The Ultimate New England Road Trip Itinerary

Last updated on September 12, 2024

New England exceeded all expectations. It was my small-town Gilmore Girls dream brought to life – I’m not sure I’ve ever used the word “charming” quite so often. Plus the nature blew my mind. From Acadia to the White Mountains to the forests and lakes of Vermont, every state has something spectacular to offer. And the history and culture is some of the richest in all of the States. It’s the part of America I could most easily see myself living in. 

We were in New England for four weeks, doing a road trip through all six states. This post has all the details of that one-month New England road trip itinerary, including all the stops we made, the places we visited and the tips we picked up along the way.

How to use this New England road trip guide

The idea is that you choose the destinations that resonate with you and create your own route based on that. Or you could simply copy our route entirely, which I’d highly recommend as it’s one of the best trips we’ve ever been on.

We’ve divided it into overall New England road trip tips, followed by guides to each destination, including things to do, places to stay and where to eat. We also delve into each destination in more detail in other posts around the site. 

The details of the first section of the road trip can be found in our Boston to Maine itinerary, which covers Boston up to Bar Harbor.

As always, just let us know if you have any questions. And don’t miss our other road trip itineraries and guide to how to plan a road trip.

Who is this route for? Families, couples?

This New England itinerary is for everyone, from couples to families to solo travellers. We did it as a family with a 3 and 5-year-old. But, as with all our Bridges and Balloons itineraries, it would suit lots of different ages and groups. 

Our style of family travel means we try to do as many “grown-up” things as we can, while also keeping the kids happy with visits to playgrounds and family-friendly museums etc. If you’re traveling without kids, just skip those more child-focused bits.

New England road trip at a glance

• Boston
• Portsmouth
• Southern Maine
• Portland
• Acadia National Park and Bar Harbor
• Camden
• White Mountains
• Burlington and North Vermont
• South Vermont
• The Berkshires
• Litchfield Hills
• Coastal Connecticut
• Providence / Newport
• Cape Cod and Martha’s Vineyard

Our New England road trip highlights

• I fell in love with New England’s small towns. A few favourites were: Bar Harbor, Camden and Ogunquit (ME), Brattleboro and Burlington (VT), Kent, New Milford and Madison (CT), Portsmouth (NH), and Great Barrington and Oak Bluffs (MA).
• We stayed in some amazing guesthouses and glamping spots along the way. Some favourites include: Fortland Maine, Lumen Nature Retreat, Basin Harbor, Homestead Madison, The Kent Collection and the Lord Camden Inn.
• There are some brilliant, characterful roadside attractions in New England, from antiques stores to family mini golf. Always keep your eyes open for fun stops along the way. My favourite find was Suzie’s Bakes, a cute bakestand by the roadside in Connecticut.
• New England has a bounty of fresh produce. Be sure to check out local farms where you can buy all sorts of goodies from cheese to maple syrup. There’s also lots of opportunity to pick your own fruit, which felt like a quintessential New England experience.
• The nature of New England is epic. Some of our favourite places were Acadia National Park, the White Mountains of New Hampshire, the endless forests of Vermont, and all the lakes that we found in pretty much every state we visited. The beaches in Main, coastal Connecticut and Cape Cod/Martha’s Vineyard are also gorgeous.

Find all the details of these places in the sections for each destination below…

New England road trip map

New England road trip FAQs

How long do you need for a New England road trip?

New England covers a vast area across six states, so if you want to see all six of them, you’ll need at least three weeks, and ideally four. But it’s also totally possible to do a smaller one-week or two-week New England itinerary, focussing on specific states and areas of interest.

We did this entire itinerary over four weeks and adopted a fairly relaxed pace, staying in some places for three nights rather than speeding through the whole thing with single night stays the whole time. This suited us, especially as we were traveling with kids, so it was nice to give them a break from back-to-back driving days. 

When to go to New England 

We, like so many people, had always planned to go to New England in the autumn when its famous fall foliage is in full bloom and leaf peepers flock to the area. But school commitments meant we couldn’t, so we opted for summer instead. And I’m kind of glad we did as, although I’m sure the fall is spectacular, summer was also amazing, especially along the coast and by the lakes. It’s a popular destination for Americans and it had a real ‘summer vacation’ vibe to it. 

The weather in New England is variable, but we were lucky to have mostly sunny days and temperatures ranging from around 24-32 Celsius in July-August. There were also a few overcast days across the four weeks and we had some pretty epic storms. It was generally pretty humid. You’ll definitely need layers (see packing tips below).

Summer and autumn are the most popular times of year, so expect bigger crowds and inflated prices. For something quieter, go in spring when the flowers start to bloom, or winter when the mountainous regions become snowy playgrounds. 

What to pack for a New England road trip

You’ll need layers for New England’s variable climate, and don’t forget a raincoat whatever the season. 

A few more essentials:

• Insect repellant, especially in the summer
• Comfy walking shoes 
• The cute little New England Field Notes by Wildsam
• Tick remover – there are a lot of ticks in New England, so it’s important to do a daily tick check. These little devices are meant to be good for removing them.

How to get around New England 

We hired a car with Discover Cars, our favourite site for rentals. They search hundreds of other rental companies and tend to come back with the best deals. They also have good cancellation/amendment policies. I also recommend Expedia. Our actual rental was with Dollar, but it’s cheaper to book through a third party rather than with them directly.  

Bear in mind it’s often cheaper to rent for a week-long period rather than an odd number of days (you often get a discount for seven days or a month), so play around with the booking dates and see what comes up. Find the latest deals here.

We did a round trip from Boston, but if you’re starting and ending your road trip in different destinations and need to return the car somewhere else, you’ll have to pay an extra fee.

How to get to New England 

The biggest airport for New England is Boston, but there are smaller regional airports too, including one in Portland, Maine. We recommend searching on Skyscanner for the best deals. You could also look into flying to New York and driving to New England through upstate New York or Connecticut.  

Tips for driving around New England

Scenic Byways

New England has some of the most picturesque drives in the USA. Follow the scenic byways, such as the Kancamagus Highway in New Hampshire, Route 169 in Connecticut, or the Molly Stark Byway in Vermont for breathtaking views. Google maps might suggest you bypass these for shorter routes, so be sure to check the route carefully and make sure you aren’t missing something spectacular.

Toll Roads

Be prepared for tolls. Keep some cash on hand or consider an electronic toll pass for convenience (if hiring a car, you can sometimes get these directly through the car hire company).

Most toll booths don’t accept payment by card, so if you don’t have cash or a toll pass, you have to pay online that day to avoid a fine. We got caught short once or twice with no change so we had to pay online.

Weather awareness 

New England weather is unpredictable, so make sure you’re prepared for varying conditions, especially during the fall and winter months. Check weather forecasts regularly, and prepare accordingly. For example you might need to re-route because of snow or ice.

Parking

In cities like Boston and Providence, finding parking can be a challenge or at least very expensive. We have specific tips for each area in the ‘How to get around’ section for individual destinations.

But as a general rule of thumb, use public transport when exploring downtown, and try to find accommodation with free parking facilities (this was really handy for us in places like Bar Harbor and Boston). Also familiarize yourself with the different parking restrictions and signs. We got a parking ticket in Boston near Fenway Park because we misunderstood the sign. 

Where are the best places to see fall foliage in New England?

If you’re doing this route in autumn, you’re in for a treat. Some of the most spectacular places to see fall foliage on this New England road trip include:

• The Kancamagus Highway, which is surrounded by forest and has some epic viewpoints. You’ve likely seen aerial shots of this road in the fall. We stopped along the way in summer and could see a blanket of forest, which I could tell would be even more stunning in fall.
• Stowe – this cute town in Vermont has a picturesque steeple church that is one of the most photographed spots in fall. You can even do foliage tours by zipline!
• Acadia National Park (especially the view from Cadillac Mountain)
• Boston Common, Arnold Arboretum and the tree-lined streets of Beacon Hill in Boston
• Route 7 in Connecticut from Norwalk to Litchfield Hills

Where to stay in New England

We stayed in some gorgeous places in New England. As you can imagine, they do charming guesthouses really well, plus there are some lush opportunities to stay in lodges amid the region’s glorious nature.

We’ve detailed everywhere we stayed in the accommodation section for each destination below. Plus we also have separate guides to the best New England family resorts, the best family resorts in Maine, and the best Vermont resorts.

Our detailed New England road trip itinerary

Boston to Maine

We’ve included all the details of our stops from Boston to Bar Harbor in our Boston to Maine road trip itinerary. Pop over there to read more detailed descriptions for Boston, Portsmouth, Southern Maine, Portland, Camden and Acadia National Park. 

In that itinerary, we recommend staying a night in Camden en route to Acadia from Portland. But if you’re doing a full New England road trip, you might like to go from Portland to Acadia and then back down to Camden before heading to the White Mountains.

This is what we did as we felt the 5-hour drive from Acadia to the White Mountains was a bit too long with kids. It’s a 3.5 hour drive to the White Mountains from Camden, which was better.

White Mountains, New Hampshire

New Hampshire’s White Mountains are stunning and world famous for being one of the best places in the world to see fall foliage. It’s a place of epic forests, towering peaks, and pristine waterfalls and lakes. You can be as adventurous or not as you like, opting to hike mountains or simply drive around the sights. 

We had woefully little time there, spending one night en route from Camden to Burlington. It was memorable, staying at Lumen Retreat, one of New England’s best glamping spots. But if I did it again, I’d spend at least two nights there so we could explore more. Really, it’s an area where you could spend a week. I’d love to visit in the fall when the Kancamagus Highway must be stunning (it’s gorgeous enough in summer).

Things to do in and around the White Mountains

• Drive the Kancamagus Highway, a winding road through dense forest and one of America’s Scenic Byways. You could do this self-driving audio tour for commentary along the way.
• Visit the Lost River Gorge & Boulder Caves or Flume Gorge where you can do a fairly easy family-friendly hike. Both were closed when we were there due to heavy rain.
• Echo Lake is the place to go for swimming and kayaking.
• We would have really liked to drive up the Mount Washington Auto Road or go on the Cog Railway. If we’d had an extra day, this is what we’d have done.
• In the winter, there’s lots of opportunity for winter sports in the White Mountains, from sleigh rides to skiing to snowmobiling.
• Storyland looks like a fun theme park for kids where children’s favourite tales are brought to life.

Where to eat and drink in the White Mountains

• Before you get on the Kancamagus, stop at the Cheese Louise Commissary for one of the best grilled cheeses of your life.
• Go to Polly’s Pancake Parlour for a perfect start to the day.
• StrEatz gourmet food truck near Lumen Nature Retreat has an inventive menu and is a cute place to hang out amid the trees.
• There are lots of breweries in the area. Shilling Beer Co in Littleton comes highly recommended with a fab location on the river. And we enjoyed a meal and beer flight at the Woodstock Inn Brewery, which was particularly good for families.
• The Moon Cafe and Bakery is a popular spot for coffee and breakfast. The scones are excellent.
• Go to Panorama Six82 at the Owls Nest resort for a cocktail with a view.

Where to stay in the White Mountains 

Lumen Nature Retreat

We stayed at Lumen Nature Retreat, a beautiful collection of minimalist Scandi-style cabins gathered beside the water. The cabins themselves are a treat, but the highlight is the barrel sauna that looks out over a pond. See the full review in our guide to glamping in New England.

Check the latest deals and book now.

Huttopia White Mountains

We didn’t stay here, but we loved Huttopia Southern Maine and all Huttopias have a similar vibe, so I’d say this is a good option too.

Check the latest deals and book now.

How to get around the White Mountains

There’s no public transport network in the White Mountains, so you will be reliant on your car.

Burlington and Northern Vermont

Bernie Sanders, the gentleman from Burlington, has put this region on the map for international visitors like me. But long before Bernie, Burlington and Northern Vermont were popular destinations for Americans, drawing people in with their breathtaking natural splendour and welcoming, community-led atmosphere.

Burlington, the largest city in Vermont, is the epicentre of the region and a place we could easily live. On the shores of Lake Champlain, it has a stunning setting and is filled with all the indie shops and restaurants you’d expect from a place where Sanders is Senator. While there, it seemed to us that everyone had a friendly, “outdoorsy” vibe.

And it makes sense because Burlington and Northern Vermont offer a natural playground with year-round activities for outdoor enthusiasts. From the Green Mountains to the lakes, you can ski, hike, kayak, bike or whatever takes your fancy. 

Add to that some cute towns like Stowe and a world-famous ice cream factory, and you have an amazing destination. It’s one of the places we loved most on our New England trip (in part due to the incredible Basin Harbor – see the accommodation section below!).

See our full guide to the best things to do in Vermont with kids.

Things to do in Burlington and Northern Vermont

• Visit the ECHO museum, a children’s science and nature museum on the waterfront in Burlington
• Rent a bike from Local Motion or Skirack to explore the city. We rented an electric one with a trailer for the kids from Skirack, and it was the perfect way to see the city.
• Go shopping in cute downtown Burlington, especially on the pedestrianised Church Street. 
• Go to Stowe, one of Vermont’s cutest towns. Walk the Stowe Recreation Path, which runs alongside the river.
• Visit the Ben and Jerry’s factory and do a tour. Be sure not to miss the ice cream graveyard where you can see all the retired flavors. And there’s also a great playground. Both the graveyard and playground are free and available without a tour.
• Make a teddy and do a tour of the Vermont Teddy Bear company. Our boys loved doing this and the teddies are now firm favourites.
• For us, one of the best things was simply hanging out at Basin Harbor on Lake Champlain (see where to stay).
• If you’re there in winter, go skiing in one of the region’s ski resorts like Jay Peak.
• Check out the local events calendar in Burlington. It was the Festival of Fools while we were there, which was great fun and had lots on for kids.

Where to eat and drink in Burlington and Northern Vermont

We’ll have more recommendations in our upcoming guide to Burlington, but here are some highlights.

• Get pizza at Piecasso Family Pizzeria in Stowe.
• If you stay at Basin Harbor, The Red Mill is a good casual option with a kids’ playground. Or go to Ardelia’s for something more fancy. We also loved the North Dock dinners on the lakeside.
• Black Sheep Bistro – upscale dining in Vergennes. The patio seating is lovely.
• LuLu’s Scoop Shop – excellent ice cream in Vergennes.
• Gaku Ramen –  authentic Japanese ramen and rice bowls in Burlington.
• Farmhouse Tap & Grill – farm-to-table gastropub in Burlington with an excellent craft beer list.
• Honey Road – women-owned eastern Mediterranean restaurant. Semi-finalist for James Beard award.
• Henry’s Diner – a very cute classic diner in downtown Burlington.
• Burlington Bay – don’t leave Vermont without trying a creemee! This waterfront stop is a perfect place to try one (excellent views of the lake too).
• Vergennes Laundry  – wood-fired bakery with amazing cakes.

Where to stay in Burlington and Northern Vermont

We’ve written a guide to the best Vermont family resorts, and here are two of our favourites…

Basin Harbor

We stayed at Basin Harbor, which reminded us of the resort in Dirty Dancing. On the shores of Lake Champlain, it has a gorgeous setting with epic views and sunsets. Hire boats, ride bikes, play pickle ball, do yoga or simply relax beside the lake. It’s the kind of place where you could easily spend a week, there’s so much to do. 

It’s fantastic for families and our kids had the time of their lives there – they especially loved the little row boats they could take out on the water. And the breakfast buffet was the best we had in New England, filled with cakes, local specialities and a fantastic made-to-order egg counter. A highlight for us was a BBQ on the lakeside where mixing with fellow guest was encouraged and we had some great conversations.

Check the latest deals and book now.

Blind Tiger Burlington

If you’d prefer to stay in Burlington, Blind Tiger has great reviews. It’s in a historic mansion and in walking distance of Church Street, so perfect for exploring the city.

Check the latest deals and book now.

How to get around Burlington and Northern Vermont

Burlington is an ideal city for cycling, which is what we did while there, hiring bikes with a kids’ trailer from Skirack. It’s pretty hilly, so Steve got an electric bike to go with the trailer. I was okay with a normal bike and no trailer. There are good cycle paths and routes in and around the city.

Burlington also has a train station, so it is a good place to visit without a car.

However, as you’re reading this post, you’re likely on a road trip so you will have a car. We found parking easily near the Local Motion hire shop. Plus a car is definitely needed for exploring Northern Vermont, like Stowe and Vergennes. 

Southern Vermont 

“It seems like 90% of Vermont is trees”, I said to Steve as we drove from Basin Harbor down to Dummerston. And my seeming hyperbole was almost correct – the actual figure is 78%! It’s also mountainous, and as such a trip around Vermont is characterised by endless forested peaks.

And between those peaks, you’ll find little one-street “villages” with not much more than a school, library and grocery store. So tiny that the bigger places, like Manchester, feel positively urban amid it all – whereas somewhere else they’d be considered small. 

In today’s world, the space and endless greenery is a luxurious opportunity to bathe yourself in nature and imagine what life was once like. Plus the region has a rich cultural heritage to explore – we even stayed in Rudyard Kipling’s old house (see where to stay below).

While you could drive directly from Basin Harbor/Burlington to the Berkshires, we recommend stopping for a night in Southern Vermont to truly get away from it all. And whatever you do, don’t leave without trying some famous Vermont maple syrup!

For our journey, we took Route 5, staying at Kipling’s estate near the historic town of Brattleboro. An alternative route would be to take route 7A, running through the Shires of Vermont with stops at Rutland, Manchester or Bennington.

Things to do in Southern Vermont 

• Visit VINS Nature Center, which includes a raptor exhibit and canopy walk (a great road trip stop with kids).
• Go to Scott Farm Orchard – if you’re staying on the Kipling estate, visit Scott Farm Orchard next door where they grow 130 varieties of heirloom apples. They also hold community events throughout the year.
• There are loads of lovely walks you can do in the area. There was a folder full of options for us at our accommodation.
• If not staying at Kipling’s Carriage House/Naulakha (although we really think you should!) and are driving down the 7 instead, stop at the historic towns of Rutland or Bennington. In Bennington, you can climb the Battle of Bennington monument, which has sweeping views of the area.

Where to eat and drink in Southern Vermont 

• The Skinny Pancake – a Vermont institution with branches across the state. We stopped at the Quechee branch for lunch en route to Dummerston. It’s a perfect family-friendly place.
• Grab a picnic from Brattleboro Specialty Cheese & Wine Shop to enjoy at Retreat Farm next door.
• Stop at Harlow Farm to stock up on goodies from the farmstand and visit the on-site cafe.
• The Vermont County Deli has loads of local goodies and does excellent sandwiches and bagels too.

Where to stay in Southern Vermont 

Kipling’s Carriage House 

Kipling’s Carriage House is one of the most unique places we’ve ever stayed. It was Rudyard Kipling’s carriage house at his home, Naulakha, where he wrote the Jungle Book and other classics. 

You can stay in Naulakha itself, which is huge and has four bedrooms, but the carriage house was perfect for us. As with Naulakha, you get the whole place to yourself, complete with a huge kitchen and refined lounge/reading room.

Built in 1895 and preserved with antique furnishings, it’s a way to experience firsthand a piece of history. I liked hearing how carnival folk used to set up stall in the neighbouring meadow, charging punters for a glimpse of the famous author. It brings to life Kipling’s world.

The Kipling estate is also a gorgeous place in itself with splendid views of the Connecticut River Valley and not far from the cute town of Brattleboro where you’ll find restaurants, shops and brewpubs.

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Inn at Manchester

If you opt for Route 7 instead of the 5, a good place to stay the night is Manchester where you’ll find the charming Inn at Manchester. This friendly bed and breakfast gets consistently high reviews. 

Check the latest deals and book now.

How to get around Southern Vermont 

Ideally you need a car to get around Southern Vermont, but there are buses between the bigger towns. Here’s a guide to transportation options in Vermont.

The Berkshires

The Berkshires are like the Hamptons – a place where city dwellers go for an upscale weekend getaway in nature. But where the Hamptons has the seaside, the Berkshires offers forest, lakes and mountains.

It’s a place with plentiful outdoor activities as well as a rich cultural calendar, including the annual, world-class Tanglewood festival (the summer home of the Boston Symphony Orchestra). The culinary scene is booming with many renowned chefs from the city deciding to up sticks and make it their home.

We stayed in Great Barrington, a picturesque town backed by mountains and with a reputation for fantastic food and hiking. While not exactly hipster, it’s the town where you’re most likely to find them. Other popular spots in the Berkshires include Lennox and Adams. 

Drive there from Southern Vermont on the Molly Stark scenic byway for beautiful forest views. 

Things to do in The Berkshires

• If you’re there in the summer, check out the Tanglewood Music Festival. They even have family days, suitable for all ages.
• Another fun event for families is the Dance Festival at Jacob’s Pillow, a renowned center for dance.
• Visit MASS MoCA art museum. The Kidspace is great for families and there are some good restaurants/cafes next door.
• Go to the Berkshire Museum to learn about the area.
• Drive to the top of Mount Greylock for fabulous views of the area.
• Go to a Berkshire Natural Resources Council property where you can hike, snowshoe, run, birdwatch, paint pictures, take photos or hunt for geocaches.
• Try ziplining, kayaking or white water rafting with Zoar or Crab Apple.
• Ride the Berkshire Scenic Railway.
• Visit the Norman Rockwell Museum.
• Hike part of the Appalachian Trail.
• Spend time at Lake Mansfield where they have a swimming area and a good playground for kids (we had a gorgeous, lazy afternoon here).

Where to eat and drink in and around Great Barrington

• The Prairie Whale – the number one restaurant in Great Barrington with top-notch farm-to-table cuisine by Marc Firth, who built his reputation in New York.
• Baba Louie’s – a cute family-friendly spot for pizza in downtown Great Barrington (our kids loved it).
• The Egremont Barn – an iconic place to catch live music. They also have a good menu of pub classics.
• Put together a picnic from Rubiner’s Cheesemongers in Great Barrington.
• Go to Steam for excellent noodles –they’re really welcoming to kids too (our fussy eaters ate very well there!)
• Get your candy fix from Robin’s Candy.
• Xicohtencatl Restaurant, just outside Great Barrington, has fantastic Mexican food and margaritas.
• Tunnel City Coffee is a good spot for coffee near MASS MoCA.
• Pixie Boulangerie has delicious baked goods.
• We also stopped at On the Run coffeeshop near Race Brook Lodge, which is a classic local coffeeshop field with regulars chatting.

Where to stay in the Berkshires 

We did a home exchange in Great Barrington for the majority of our stay in the Berkshires, and definitely recommend the town as a great place to base yourself.

A highly recommended hotel and one that caught our eye is the Wainwright Inn, which is a beautiful historic building. Another favourite is The Barrington, a more modern boutique hotel right in the centre of town.

Race Brook Lodge

We also stayed a night in the unique Race Brook Lodge, a sprawling, ramshackle property with a rich history and creative spirit. All rooms at the rustic family-run lodge are unique, furnished with antiques and homely decor. And there’s an atmospheric shared common room with wood panels, plenty of games and a big kids playroom. Pre-covid, there was an honesty bar, but that’s currently closed. You can, however, still order food and drinks to your room/the common area via text.

There’s also a pool, playground and a big barn that hosts events. While some of the facilities feel a little faded, it’s also one of those hidden gems that’s a joy to experience. 

Our only quibble is that the onsite Stagecoach Tavern restaurant is a little too expensive – it doesn’t quite match the vibe and prices of the lodge, so we’d have preferred to see a more casual menu on offer. That said, there are places you could easily drive to eat nearby.

Check the latest deals and book now.

How to get around Great Barrington and the Berkshires

Great Barrington is easily walkable, but you’ll need a car to explore the wider area. Find out more about getting to the Berkshires here.

Litchfield Hills, Connecticut 

I won’t lie, our prime motivation for visiting the Litchfield Hills area of Connecticut was to find the real Stars Hollow (I’m a huge Gilmore Girls fan!). And it lived up to the expectations, being rich in cute small towns filled with independent bookshops, cafes and Doose’s style supermarkets. And yes, of course you’ll find gazebos on the town greens too.

If you’re a fellow Gilmore Girls fan, be sure to see my guide to where to find the real Stars Hollow.

And even if you’re not a fan, this is an area full of charm and community spirit. We stayed in Kent, a one-street town where we slept in a stylish train carriage, visited the local farmers market, ate exceptional food, and generally soaked up the small town life. 

Things to do in Litchfield Hills, Connecticut 

• Enjoy the small-town life in places like Kent and New Milford.
• Do a wine tasting or have a meal at Hopkins Vineyard.
• Hike, see the covered bridge and visit the waterfall at Kent Falls State Park. See more hiking options here.
• Go to a local event at Kent Barns.
• Visit the Railroad Museum of New England where you can ride an old steam train.
• Go to the New England Carousel Museum in Bristol.

Where to eat and drink in Litchfield Hills, Connecticut 

• Swyft – a beautiful farm-to-table restaurant in Kent
• Fife and Drum – fine dining and a lively bar in Kent
• Get coffee from Marty’s Café or Po’s Café in Washington Depot; The Villager Café or Wilson’s in Kent; or Theo’s Downtown Diner in New Milford.
• Just outside of Kent near Cornwall Bridge is an amazing bakestand called Suzie’s Bakes. I live for homemade cakes like this!

Where to stay in Litchfield Hills, Connecticut 

The Kent Collection

The Kent Collection has a collection of properties, including two beautiful small inns. One is even called the Firefly Inn as a nod to the Gilmore Girls!

We stayed in their train carriage, which wasn’t our first time staying in a train, but was certainly the most stylish. It’s been impeccably renovated with a tasteful railway theme and cosy wooden interiors.

There’s a fire pit outside for roasting s’mores in the evening, and it’s right in the centre of Kent. The train carriage sleeps four and would suit both couples and families. It was one of the highlights of our New England trip. 

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Mayflower Inn and Spa

For something more fancy, stay at the Mayflower Inn and Spa, which is where Amy Sherman-Palladino was inspired to set the Gilmore Girls in New England.

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How to get around Litchfield Hills, Connecticut

This area of Connecticut is definitely a place where you need a car. The small towns are walkable but there’s no public transport to connect them.

Coastal Connecticut

We loved our time in coastal Connecticut. The little towns along the shoreline of Long Island Sound have that classic New England charm with the added bonus of being beside the sea.

We stayed in Madison, which had a Stars Hollow vibe in terms of community. We even saw a group of locals holding a “Welcome to Madison” event for newcomers to the town. And the beaches were gorgeous, perfect for families with playgrounds next to the sand.

Probably the most famous town along the coast is the historic seaport and somewhat bohemian Mystic (yep it’s the “Mystic Pizza” one!). And there’s also the city of New Haven, home of Yale and, as locals may tell you, the best pizza in America (just don’t say that to a New Yorker!). Norwalk also has some great museums, and is home to the best diner we’ve ever been to.

Things to do in Coastal Connecticut

• Visit Mystic Seaport, a living maritime museum that takes you back in time to the 19th century and features impressive tall ships.
• Go to the Maritime Aquarium in Norwalk where you can learn about the aquatic life of the Long Island Sound. There are some great interactive exhibits and touch pools for kids.
• Stepping Stones in Norwalk is a fantastic children’s museum with loads of hands-on exhibits for kids aged up to around 10. Our boys could have stayed there all day.
• There are some good opportunities for fruit picking in Connecticut. We enjoyed blueberry picking at Bishop’s Orchard. 
• Coastal Connecticut has some gorgeous beaches. We had a lush afternoon at the Surf Club on Madison Beach, which is an easy bike ride from where we stayed at Homestead Madison. Other popular beaches along the coast include: Silver Sands State Park in Milford, Jennings Beach in Fairfield and  Hammonasset Beach State Park in Madison.
• If you go to New Haven, do a tour of Yale. And make sure to try some pizza.
• Visit some of the cute little towns like Madison, Stonington, and Essex.

Where to eat and drink in Coastal Connecticut

• We went to a fun evening event at Bishop’s Orchard farm where they had live music, food trucks and wine from the farm (the wine slushie was ace!).
• Lenny and Joe’s is a classic casual roadside seafood restaurant with generous portions and good prices. There’s an old fashioned carousel for the kids.
• The Post Road Diner is one of the best diners we’ve ever been to. A real classic with everything you expect, from chrome interiors to staff who call you honey.
• In Norwalk, the Barcelona Wine Bar has excellent reviews. We were headed there before the Post Road Diner caught my eye!
• Make sure to try pizza in New Haven – or ‘apizza’ to use the correct regional term. The most popular spots are Modern Apizza, Sally’s Apizza and Frank Pepe’s Pizzeria.
• Mystic Pizza from the 80s rom-com is an actual place! Go there for your own “slice of heaven’.
• Mystic is also known for its seafood. The Oyster Club is one of the most popular spots in town.

Where to stay in Coastal Connecticut

Homestead Madison

We loved Homestead Madison. It’s one of those guesthouses that oozes character and where you can see the owners – Ralph Guardiano and his daughter – have gone above and beyond to create a memorable, special stay. We could have happily stayed there a week. 

Ralph’s a producer and has an impressive collection of memorabilia that can be found on display throughout the inn. There’s even a cup that went down to the Titanic! And as you enjoy breakfast in the morning, you’ll find an almost life-size giraffe overlooking your table. 

Snacks and drinks are available throughout the day, including fresh sweet treats, coffee, and popcorn from a vintage machine. Come nighttime, enjoy complimentary port and s’mores by the firepit. 

And the rooms themselves are cosy with spa showers, comfortable beds and record players where you can spin LPs from Ralph’s collection. 

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The Study at Yale

If you’re staying in New Haven, The Study at Yale looks like a great option. It’s on the university’s Arts Campus and all the rooms are themed with a collegiate style and have attractive campus views. 

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The Whalers Inn

If you want to base yourself in Mystic (although we really recommend Madison), The Whalers Inn comes highly recommended.

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Providence / Newport

Rhode Island is the smallest state in the USA (it only takes an hour to get from one side to the other!), but it attracts many visitors, being an easy weekend trip from Boston and New York. The two main places to visit are the state capital, Providence, and Newport, a coastal town famous for its Gilded Age mansions. The beaches are also gorgeous.

We only went to Providence, but would have loved to visit Newport too. Cliff Walk looks spectacular, and the whole place has that charming seaside town vibe that I love. One option would be to do a guided day trip from Providence to Newport.

We were short on time and didn’t really get under the skin of Providence, but it has a reputation as a vibrant, creative city, in part due to being the location of Brown University and the Rhode Island School of Art and Design. And in the summertime, it hosts the famous WaterFire event on the river. The food scene is also thriving.

Things to do in Providence / Newport

• Visit Waterplace Park in Providence for a scenic stroll along the river. Don’t miss the epic WaterFire events in the summer.
• Explore the Rhode Island School of Design (RISD) Museum, known for its exciting art collections.
• Take a walk through Providence’s Benefit Street, lined with historic homes from the 18th century.
• Roger Williams Park in Providence has a great zoo and you can also ride the swan boats.
• Do a guided tour of Providence.
• Marvel at the mansions on Newport’s Cliff Walk, including The Breakers and Marble House.
• Enjoy the views of the harbor from Fort Adams State Park.
• Hit the beach in Newport. Popular spots include Easton’s Beach and Second Beach.

Where to eat and drink in Providence / Newport

• Head to Providence’s Little Italy in Federal Hill where you’ll find family-run institutions like Joe’s and Angelo’s.
• We didn’t eat here, but we liked the look of Ogie’s Trailer Park.
• Try local seafood at Hemenway’s Seafood Grill & Oyster Bar.
• Head to the Providence River to find exciting food trucks.
• We liked the look of this food and crime tour of the Federal Hill area!
• Go to Clarke Cooke House for seafood. Or grab a classic lobster roll at Flo’s Clam Shack.
• The White Horse Tavern in Newport is well reviewed for farm-to-table dining.

Where to stay in Providence / Newport

Omni Providence Hotel

We stayed at the Omni Providence Hotel in the centre of downtown Providence. While a downtown location would never be my first choice, it did have fabulous views of the city, including the capital building. 

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How to get around Providence and Rhode Island

Rhode Island has a good public transport network via the Rhode Island Public Transit Authority (RIPTA), which offers bus and trolley services around the state.

And Providence has an airport and train station, so is well connected to the rest of the country. The MBTA runs between there and Boston.

Parking is fairly easy in Providence and you can pay via a handy app

The easiest way to get around Newport is with the RIPTA trolley.

Cape Cod and Martha’s Vineyard

Martha’s Vineyard was one of the places I was most looking forward to on our New England road trip. It had an almost mythical image in my mind, created through years of reading about it in novels. And blogger Alex in Wanderland’s stories about life there sound dreamy. 

We were lucky to secure a Home Exchange on the island so spent five days there, exploring the island and being delighted to find it did indeed live up to the hype.

It’s an interesting mix of seaside town kitsch and elegant, upscale towns. Go to Oak Bluffs for the first and Edgartown for the second. And even with the kitsch, Oak Bluffs is still charming, especially The Campground where you’ll find those iconic Gingerbread Houses.

I fell in love with the island as much as I’d hoped to. But there are also many other options around Cape Cod. You could stay on the Cape itself, heading up to cool Provincetown at the tip. Or take a trip to Nantucket, ‘The Faraway Island’ for a quieter, more rural take on island life.

Things to do on Martha’s Vineyard

• Jump off the Jaws Bridge where the famous movie was filmed (there’s Jaws memorabilia everywhere in Oak Bluffs!)
• Hit the beach. Some of the most popular spots include South Beach, Joseph Sylvia State Beach and Inkwell Beach.
• Do the African-American Heritage Trail, which includes 22 sites that tell the island’s fascinating Black history. To this day, the island is a popular vacation spot for African Americans – Obama even has a home there.
• Visit the Martha’s Vineyard Museum to learn about the island’s history and culture.
• Visit the alpacas at Island Alpaca
• Explore the Cape Poge Wildlife Sanctuary on Chappaquiddick Island
• Enjoy the epic views and cool formations of the Clay Cliffs of Aquinnah (formerly known as Gay Head)
• Hang out in Oak Bluffs and ride the vintage Flying Horses Carousel.

Where to eat and drink on Martha’s Vineyard

• We loved Morning Glory Farm near Edgartown, which has incredible baked goods as well as the Moglo Food Truck, serving some of the best breakfast sandwiches we had in New England.
• Mad Martha’s is our favourite spot for ice cream in Oak Bluffs
• The Lookout Tavern and Nancy’s are really popular for seafood and have good views of the water
• Biscuits cafe is never without a queue in Oak Bluffs
• Backdoor Donuts is an Oak Bluffs institution, opening in the day and then again at night when the queue is always heaving.
• The Port Hunter is popular in Edgartown
• And we also loved the Behind the Bookstore Cafe in Edgartown (the bookshop itself is also excellent)

Where to stay on Martha’s Vineyard

We were lucky to do a Home Exchange on Martha’s Vineyard in Oak Bluffs, which gave us an insight into local life. Accommodation otherwise tends to be fairly expensive, especially during the peak season. You can find a full run-down of the options here. And these are a few that caught my eye.

Gingerbread Airbnb

Fellow blogger Alex in Wanderland lets out her adorable gingerbread house in the Campground in Oak Bluffs. 

Oak Bluffs Inn

Oak Bluffs Inn had a lovely vibe whenever we walked past with lots of guests gathered on the porch. It’s in an exceptional location and the reviews are just as good.

Hob Knob

Hob Knob is an elegant boutique hotel in a beautiful Gothic Revival home in Edgartown. Kelley House also looked like a stylish option.

How to get around Martha’s Vineyard 

Martha’s Vineyard has a good bus system, the Vineyard Transit Authority (VTA). It connects Edgartown, Oak Bluffs, Vineyard Haven, Aquinnah, Chilmark, and West Tisbury, so you can easily get around without a car.

This is important because it’s actually pretty hard to bring a car to Martha’s Vineyard. There is a car ferry, but it books up months in advance, and we were unable to get a spot on it. On the other hand, it’s usually possible to simply walk-on as a foot passenger (but if I were you, I’d book in peak season just to be on the safe side). 

Here are more details about how to get to Martha’s Vineyard by boat. Note that there are arrival points in Oak Bluffs and Vineyard Haven, although the Oak Bluffs dock is only open in the high season. You can catch the ferry from mainland Massachusetts at Hyannis, Falmouth or New Bedford. And it’s also possible to go direct from Rhode Island at Quonset Point. 

There’s also an aiport in Vineyard Haven.

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