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Summer in New England: 15+ Awesome Weekend Trips From Boston

Summer in New England can be an idyllic American experience with small town charm, great beaches and even better seafood. In summer, New England is blessed with so much nature and good weather that you spend a large part of the time outdoors. For culture vultures, the best weekend trips in New England also include time spent at festivals from jazz to film and books. Here we look at some of the best places to visit for weekend trips in New England. Although chosen for accessibility as weekend trips from Boston, some of these New England destinations make great weekend trips from New York City as well.

Connecticut

Connecticut makes for easy weekend trips in New England being convenient from both Boston and New York City.

We have visited Litchfield County with friends and by ourselves several times. Although Litchfield county is well known as a fall destination in New England because of the vibrant colors of its foliage, we also enjoy it’s small town America charm during the summer. Boston to Litchfield is a couple of hours drive.

We think Mystic is better suited for summer in New England with children as there is so many activities for them to do. The drive from either New York or Boston to Mystic is a couple of hours. Haven driven Boston-New York many a time, Mystic is a convenient mid-point for the trip.


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Litchfield County

Litchfield county is a Connecticut’s largest county but the lowest in population. Located in Northwestern Connecticut, it shares a border with the Berkshires which runs into the state of Massachusetts. Locally, the Berkshires are known as the Litchfield Hills and everyone else in the country knows them as part of the Appalachian mountains.

With its rolling countryside and little towns, Litchfield county is as picturesque as summer in New England can get. We remember seeing our first tractor pull at a festival at the little town of Washington, named for George Washington who rode through several times during the American revolution.

 

Litchfield county is one of the best weekend trips from Boston for adults with antiques and art galleries galore. Check out the Haight Brown Vineyard, the state’s first vineyard with a small tasting room and a lovely patio with a view over the 10 acres of vines. The Litchfield Jazz Fest has been running for almost 25 years every July and attracts some big names. The town of Litchfield is also very pretty – lots of white colonial architecture set around a village green.

There are plenty of bed and breakfasts in Litchfield and the surrounding towns. We have also stayed at the Mayflower Inn and Spa in Washington, Litchfield county.

purples flowers in a window box, white shutters, brown wooden exterior in Litchfield county USA
On your weekend trips from Boston, escape to the idyllic countryside of Litchfield County in Connecticut.

Mystic

Being a child of the 1980’s, the first I head of Mystic Connecticut was from the movie Mystic Pizza (1988) which propelled Julia Robert to fame as a waitress at the pizza joint. Mystic Pizza is still there and still booming a place as ever with both takeout and eat in restaurant options.

Mystic Connecticut though is more than its pizza fame. The little downtown area is charming with lots of little boutiques as well as the obligatory Black Dog store. In terms of weekend trips Boston and New York are nearby cities. The town of Mystic lies on the Mystic River so there’s plenty of water based activities for that summer in New England feel. There’s even an annual Maritime Music festival in June.


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There’s a lot to do in this town making it one of the best weekend trips in New England. Family-friendly options include the Mystic Aquarium with its Beluga whales. Next door to the Mystic Aquarium is Olde Mistick which is a little shopping center set up like an 18th century village.  The Mystic Seaport Museum has sailing ships as well as a living village experience with costumed actors giving explanations. My kids were also fascinated with just watching the Mystic River drawbridge in action.

All the big hotel chains like Hyatt, Hilton and Marriott have a presence in Mystic but we preferred staying at the historic mansion turned hotel, Inn at Mystic.

Charles W. Morgan The Last Wooden Whaleship in the World Built and launched in 1841
Mystic Connecticut has a a maritime museum as well as an aquarium making it perfect for weekend trips from Boston with kids

Maine

Maine has thousands of miles of coastline making it a great destination for summer in New England. The temperature averages a comfortable 70ish degrees in July and August making it great for outdoor activities.

Although Ogunquit is less than a two hour driving time from Boston, go as far north as Bar Harbor and Acadia National Park can take 5+ hours.



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Acadia National Park

The only national park in New England, Maine’s Acadia National Park is the perfect summer getaway for outdoor enthusiasts. Whether you enjoy hiking, kayaking, biking, building sandcastles on Sand Beach, or even just driving around Mount Desert Island there is something for everyone.

We spent three days in Acadia National Park and left feeling as if we needed even more time to explore. Some highlights of Acadia include the Beehive Trail, the popular Bass Harbor Lighthouse, sea kayaking with seals and porpoises, and biking the carriage roads around Eagle Lake.

If you do make the trip, take time for some fantastic food including lobster rolls, New England clam chowder or lobster bisque, and Jordan Pond House’s famous popovers.

I recommend staying in downtown Bar Harbor at cute bed and breakfasts like Primrose Place and if you do nothing else during your visit, be sure to start your day early to get a glimpse of a phenomenal Acadia sunrise (I promise it’s worth it).

– Danielle Schleig, Wanderlust While Working

Sunrise at Otter Point Acadia
Just a mere 5 hour drive from Boston, experience sunrise at Otter Point in Acadia for one of the best best long weekend trips from Boston (Image credit: Danielle Schleig)

Bar Harbor

Bar Harbor, Maine provides the perfect mix of mountains and rugged ocean coast creating scenic views for miles.

Located in southeast Maine on Mount Desert Island, Bar Harbor is the Gateway to Acadia National Park, known for its stunning scenery. Here you can hike and bike beautiful trails and canoe or kayak on the lake. Ride aboard a lobster boat out on the ocean and go whale and seal watching.

The city sits at the foot of Cadillac Mountain – the highest point along the North Atlantic seaboard and one of the first places in the country to see the sunrise. Viewing the sensational sunrise from the summit should be on everyone’s Bar Harbor bucket list.

Another experience not to miss includes a short walk over a land bridge taking you to Bar Island. This area is only accessible during low tide, otherwise it’s under water and part of the ocean floor!

Enjoy fresh lobster, clams, scallops, and oysters at a variety of restaurants in town.

Whether you desire to lodge in a luxurious inn, stay in a bed and breakfast, or rent a quaint cottage, Bar Harbor provides accommodations for every traveler.

Bar Harbor abounds with outdoor beauty and enjoyment making it the perfect New England summer getaway.

– Deanne Haines, Scenic and Savvy

View of Bar Harbor in Maine
For long weekend trips from Boston to Acadia National Park, stop by Bar Harbor, known as the gateway to Acadia (Image credit: Deanne Haines)

Deer Island

The downeast region of Maine is full of natural wonder. In the state’s gorgeous Penobscot Bay lay some of New England’s most picturesque islands. Among them is the perfect American destination, Deer Island, Maine.

Deer Island is a great destination for couples seeking a romantic getaway, families looking for kid-friendly fun in nature or groups who enjoy outdoor activities. The way of life is peaceful and laid back, and you notice that immediately upon reaching Deer Island. It has all the charms of small town America like a local playhouse and shops selling homemade local jams.

The biggest draw for visiting Deer Island is the unspoiled nature. The island is home to several nature preserves but a favorite of most visitors is Crockett Cove Woods Preserve. The forest there is a fog forest, meaning the forest floor is covered in a layer of moss and lichen.

You can also enjoy the natural elements of Deer Island from the water. Canoeing and kayaking is a popular activity and rental companies are all over the island to provide equipment or tours.

The island has a lot of cottages and bed and breakfasts to rent for your stay like the Inn on the Harbor. A more budget-friendly option is to stay at Deer Island Hostel, but you can’t go wrong in this gorgeous destination.

– Derek Hartman, Robe Trotting

kayaking on Deer Island maine
Get out and enjoy nature such as on weekend trips to Deer Island (Image credit: Derek Hartman)

Kennebunkport

The Kennebunks are the collective name for the town of Kennebunk and the harbor, Kennebunkport. Both are connected by a bridge to create one entity. The Kennebunks are quintessential summer New England towns – fresh seafood, antique stores and cold ocean water beaches.

Historically, Kennebunk was a fishing and shipbuilding village. Now, it’s more known for luxury vacations along the lines of Martha’s Vineyard or Nantucket. The whole summer vacation ethos started in the mid to late 19th century. The most famous summer residents are the Bush Family who have a compound near Kennebunkport.

Just like in Ogunquit, Maine and Newport Rhode Island, there’s an easy cliffside walk on Parsons Way that provides stunning views of both mansions and the ocean. For a family holiday, there are plenty of things to do in the Kennebunks from the beaches to the Trolley Museum which is devoted to mass transit transportation. The tours you can take in town range from food tours to town trolley tours, lobster ship tours and whale watching trips.

We stayed at the White Barn Inn and Spa in Kennebunkport. One of our favourite holiday memories was the waiter at the White Barn Inn restaurant telling me that I had made a very good choice when I ordered the water. We also amused ourselves at dinner trying to decide if the waiter’s French accent was fake. In any event, the food and service at the dinner was excellent as was our hotel stay.

In terms of family-friendly accommodation, we have friends who like The Lodge At Cove Inn (3 star) for families with young children. They liked the rooms but thought the pool was overrun with little ones. Next time we go, we want to try glamping at Sandy Pines Camping which looks like a lot of fun, especially for our outdoorsy teen kids.

The bridge to Dock Square in Kennebunkport, Maine
The bridge to Dock Square in Kennebunkport, one of the best weekend trips from Boston with kids.

Ogunquit

Having spent a July 4th weekend with friends in Ogunquit Maine several years ago, we can say that it’s a perfect place for short trips from Boston. In less than a couple of hours, you can cross New Hampshire and be in southern Maine. Along the way you pass Kittery Outlets which is an eyesore but does have good value shopping.

Ogunquit is more of what you would expect from ocean-side weekend trips in New England in the summer – lots of fresh seafood and beaches bordering the brisk ocean. Maine actually harvests the most lobster in the USA so you will definitely want to try the lobster here.

The cliffside walk is called Marginal Way and it’s an easy walk with mansions on one side and ocean on the other. Activities for fun weekend trips New England style include trolley tours through the town or boat tours and sunset sails on the water. The Neddick Nubble Lighthouse is a beautiful structure but not open to visitors.

We stayed at Cliff House which had fantastic views of the July 4th fireworks over the water.

Ogunquit Beach with the tide out at sunset
In terms of weekend trips New England has places like Ogunquit Maine with its beautiful beach and great coastal walk

Windjammer Cruises

When it comes to great summer places to visit in New England, there are so many choices. But perhaps nothing combines a slow travel adventure with an immersive slice of New England’s sailing history quite like a Maine Windjammer Cruise on Penobscot Bay.

A windjammer cruise by definition goes wherever the wind takes you, and generally appeals to the adventurous spirit who’s looking to stop the clock and unplug for a while.

The fleet of historic windjammer cruises in Maine is small — only about a dozen original schooners still sail out of Rockland and Camden for 3-7 night cruises. Some ships have been renovated to accommodate luxury travelers, while others offer a more rustic experience.

But they all have several things in common: the cuisine is typically outstanding, ships accommodate small groups around 20 or less in cozy accommodations, and the simple pleasures of the day are celebrated like reading, chatting, napping, or exploring ashore on daily excursions. Guests can even pitch in to help with the sailing and rigging if they choose.

If you’re looking for a unique New England travel experience, hop a windjammer cruise, pack light, and experience the maritime history of mid-coast Maine.

– Lori Sorrentino, TravelinMad

Windjammer cruise in New England
In summer, New England presents opportunities for a Maine Windhammer cruise (Image credit: Lori Sorrentino)

Massachusetts

Massachusetts is one of the larger New England states with some of the best long weekend trips from Boston. At about an hour’s drive, both Rockport and Old Sturbridge Village are short trips from Boston. Going across the state, however, to Williamstown and the Berkshires can take about 3 hours.

Summer traffic to Cape Cod and the Islands can be terrible as it seems all of Boston is on its way to the shore. Technically driving time from Boston to either Chatham or Falmouth should take between 1-2 hours. You need to take ferries to the islands of Martha’s Vineyard or Nantucket from either Woods Hole or Hyannis. Alternatively, you can also fly from Boston to Hyannis in Cape Cod or either Martha’s Vineyard or Nantucket.

Cape Cod and the Islands

For a timeless summer in New England experience, you can not beat time spent on Cape Cod and the Islands. The weather is near perfect in July and August with daytime temperatures in the high 70’s and low 80’s.

The towns of Cape Cod are all different from artistic Provincetown to preppy Chatham. The Kennedy family compound is in the biggest town, Hyannis. The Cape Cod National Sea Shore covers 40 acres of beaches and ponds. Try the Cape Cod Rail Trail or the Shining Sea bike path for a fabulous biking experience. Go seal watching off the coast of Chatham at Monomoy Island. Keep in mind though along with the seals come sharks who spot seal dining opportunities.

We are partial to Martha’s Vineyard obviously. Before settling on Martha’s Vineyard though, we did look at buying Chatham as well. In the end, we decided we just couldn’t deal with how busy Chatham got in the summer. We wanted our summers to be an escape from the traffic and crowds of city life. Getting to an island may be a pain but at least it limits the number of people on the island!

Martha’s Vineyard and Nantucket are smaller variations of the whole Cape Cod experience. Less strip malls, more charm. On the other hand, the price of all that charm means no theme parks for the kids (such as Water Wizz or the Cape Cod Inflatable Park).

In Chatham we have stayed at the Chatham Bars Inn which has a great beachside location. Friends, however, who stayed there last year said it was looking tired and overcrowded. We have also stayed at Chatham Inn right on the Main Street.

On the other end of the Cape, we have stayed at Inn on the Square in  Falmouth. The Cape Cod Family Resort in West Yarmouth has been recently renovated and provides a good value stay.

A welcome to Chatham sign with shark bite marks
Chatham is perfect for weekend trips, Boston is only a couple of hours away.

Rockport

Rockport, Massachusetts is a perfect place to enjoy summer in New England! Just 30 miles north of Boston, on Cape Ann, Rockport is artist’s colony meets traditional fishing village meets charming vacation town. It truly is a one-of-a-kind place.

Rockport is small, so in the summer months it can get very crowded. But there is a reason that people flock here to enjoy the area. While in Rockport, you’ll want to make sure you take a stroll along Bearskin Neck, a tight collection of shops and restaurants right along the harbor. You can pop into quirky art galleries, grab delicious ice cream, or settle down with a classic lobster roll and watch the boats.

There is so much to do in Rockport. You’ll want to get out on the water if you can: either by renting a kayak or joining a boat trip. You can head to nearby Gloucester for whale watching with one of my favorite companies: 7 Seas Whale Watching.

And of course, there are beaches! Long Beach, between Rockport and Gloucester, is your best bet for a wide, sandy beach. Perfect for enjoying a hot summer’s day.

While in Rockport, there are many places to stay, I enjoy the Rockport Inn & Suites. It is not right downtown in Rockport, but I think this allows vacationers to escape the hustle and bustle and have a more comfortable and spacious place to stay that has all the desired amenities.

– Amy, New England With Love

Rockpart Massachusetts harbor
In a little over 3 hours from Boston, you can be enjoying Rockport Massachusetts, one of the best weekend trips from Boston (Image credit: Amy Hartle, Two Drifters)

Old Sturbridge Village/Brimfield

For historical weekend trips from Boston, visit Old Sturbridge Village another living history museum. This museum is very large and took us all day to see it all. The village is comprised of a farm, houses and stores with costumed actors showing how things were done in bygone times.

We were mildly amused when we saw a large group of Amish people visiting. We weren’t sure what they could learn about living in the past when they were doing similarly themselves in the present.

Brimfield Antiques Flea Market is held nearby Old Sturbridge Village. This antiques show runs for about a week on specified weeks in May, July and September. This show began in the 1950’s and has hundreds of vendors.  Wear comfortable shoes – this show is ginormous and a treasure trove of everything from antiques/vintage to garage sale stuff.

Children are welcome to visit Brimfield and there’s always stuff to look at. There’s a giant food court too that they can visit. Brimfield though isn’t anywhere as much fun as nearby Six Flags New England.

Old Sturbridge Village has accommodation at the Old Sturbridge Inn and Reeder Family Lodges. There’s also bed and breakfasts and inns nearby. The Old Sturbridge Inn does good value packages that include staying at the Inn  and visiting Sturbridge Village and/or visiting Six Flags New England.

dyeing yarn as done in the 19th century
A museum worker showing how dyeing works at Old Sturbridge Village, one of the educational long weekend trips from Boston

Williamstown

Williamstown is nestled in the Berkshire Mountains in the the northwest corner of Massachusetts, a few miles from the borders of New York state and Vermont. Incorporated in 1765, Williamstown is home to Williams College, my alma mater. It is a quintessential New England college town, complete with a white Congregational Church on the green.

Summer activities abound. You can largely enjoy Williamstown’s charm without using your car. When there’s not a pandemic mandating the closure of many institutions, popular summer activities include:

  • A trio of world class art museums: the Clark Art Institute, the Williams College Museum of Art, and the Massachusetts Museum of Contemporary Art;
  • The Taconic Golf Club, an historic, scenic, par 71 golf course; and
  • The Williamstown Theatre Festival that attracts well known actors and has incubated plays that end up on Broadway.

For hiking, Williamstown is crisscrossed by many hiking trails and is home to Mount Greylock, at 3489 feet, the highest peak in Massachusetts. For those looking for less of a challenge, ask about the Pine Cobble Trail.

Eating in Williamstown: Walk down Spring Street, the 1 block long “commercial hub” that is home to an ever changing array of eateries appealing to the college crowd. Off Spring Street, I can personally recommend, Mezze Bistro and Bar, a farm to table restaurant where students would likely take their parents for a pricier meal.

Where to Stay: Check out the old stalwart, but moved and newly imagined Williams Inn. There is also a choice of motels and Bed & Breakfast inns. Book ahead. Williamstown is a popular summer destination.

– Suzanne Fluhr, Boomeresque

President's House, Williams College, Williamstown, MA
For a summer New England break away from the shore Williamstown is one of the best weekend trips from Boston (Image credit: Suzanne Fluhr)

New Hampshire

New Hampshire may have a limited ocean front but there’s plenty of water options nonetheless. New Hampshire has dozens of lakes with the largest, Lake Winnipesaukee covering 71 square miles. For a different kind of summer New England experience, head into the White Mountain National Forest. Driving from Boston to the White Mountain National Forest takes a bit over 2 hours.

White Mountain National Forest

The White Mountains of New Hampshire are spectacular in any season. Most flock here for the remarkable fall colors.

There are many things to do for all skill levels whether you are a thrill-seeker or a needing a family adventure. Whatever your looking for these mountains have it.

Foremost is hiking trails, the most popular trails are Mt Chocorua and Tuckerman’s Ravine.  However, solitude can be found on the lesser known trails such as Osceola Mountain located off the Kancamagus Highway or West Rattlesnake with great lake views.

If swimming in a cool mountain stream is your idea of summer fun, try taking the backroads off RT112, finding that special swimming hole along the Swift River or the Wild Ammonoosuc River.  The large smooth rocks create refreshing pools and natural waterfalls to relax in.

Maybe a scenic drive-getting lost on the backroads is your way to discover hidden farm stands with fresh produce, find wooden covered bridges, visit a winery or eat at a diner-style restaurant where the locals go for homemade meals.

Find a cozy bed & breakfast in Lincoln, Bath or Conway New Hampshire, take your time and enjoy the beauty these mountains have to offer.

– Wendy Norton, Travel The Parks

White Mountains in New Hampshire
Long weekend trips from Boston to the White Mountains involves lots of outdoors fun (Image credit: Wendy Norton)

Rhode Island

New England’s smallest state is packed with fun summer destinations. Driving from Boston to Newport takes about two hours and to Block Island 3+ hours (because of the ferry needed).  You can also fly from Logan Airport in Boston directly to Block Island.

Block Island

Block Island is a small island off the coast of Rhode Island.  It has some beautiful pristine beaches that are not crowded. Some are ideal for clamming or fishing.  There are also plenty of trails for hiking or biking. You can also visit the two historic lighthouses on the island and take in the stunning views from the cliffs.

Block Island also has lots of shops where you can find unique gifts.  In the evenings, you will have plenty of bars and restaurants to enjoy.  If you like lobster, you will be in heaven because it is relatively cheap!

It’s not the easiest place to get to, it’s best to take a ferry to Block Island.  The journey is worth it!

The National Hotel is located right in the middle of the town, so it’s a convenient place to stay.  It has a wonderful restaurant, The Tap & Grille, and is listed on the National Register of Historic Buildings.

– Anisa Alhilali, Two Traveling Texans

a beach on Block Island
Long weekend trips from Boston include visiting places like Block Island which feels a world away from the city. (Image credit: Anisa Alhilali)

Newport

Founded in 1639 Newport, on the coast of Rhode Island, America’s smallest state 75 miles south of Boston is one of New England’s great summer cities.

No other city boasts such a calendar of fun filled experiences. The annual Flower Show, Folk and Jazz Festivals, the Hall of Fame Tennis Championships and International Boat Show just some of the many events.

But Newport is not just organised festivals and celebrations. Home to the America’s Cup between 1930 and 1983 Newport is often referred to as the ‘Sailing capital of the world’. Where better to enjoy water sports and other outdoor activities such as cycling or hiking?

Alternatively a walking tour of the famous colonial mansions sitting proudly along scenic clifftop trails is a magnificent way to enjoy the crisp sea air. These elegant mansions once summer homes to America’s richest families are a fascinating insight in to the Gilded Age of the late 19th Century.

In addition to its charming boutiques and historic accommodation options such as Hotel Viking Newport’s fine restaurants serving local seafood, wines and beers affords the perfect end to your stay in this glorious city.

Newport, Rhode Island truly has something for everyone.

– Paul Rought, The Two That Do

Visiting Newport Rhode Island with kids?  We give you the lowdown on

Newport Rhode Island cliff walk with views of water
For weekend trips, Boston city slickers can enjoy the small town charm of Newport, Rhode Island (Image credit: Paul Rought)

Vermont

Summer in Vermont is also for outdoor activity lovers. The mountains and rivers of Vermont give you plenty of opportunities for land and water based activities such as hiking, kayaking and fishing.

Driving to Waterbury or Burlington for your weeekend trips from Boston takes 3 to 3 1/2 hours.

Burlington

Summer is one of the best times of the year to visit the New England region and the small, hip city of Burlington, Vermont is thriving with activities, interesting eateries (including a historical food tour), and surrounding sights.

The city is located by Lake Champlain, and one can enjoy several water-based activities like swimming, kayaking, boating, and paddling in the warm months. Families can also bike to the interconnected islands on the lake. The waterfront is great for a walk during sunset too.

Because the city has been home to several migrant communities, one can easily witness their influence on the food culture. We were surprised to find Nepali, Japanese, and even middle eastern restaurants and specialty French-style bakeries. One can also find small makers, food vendors, and local produce at the Sunday farmer’s market held in the town center.

The Essex Resort & Spa with its indoor and outdoor pools and tastefully done up rooms would be our choice of stay in the city.

– Supriya Manot, Fun Travelog

Burlington Vermont on Lake Champlain
Trips from Boston to neighbouring Vermont could take you to Burlington and majestic Lake Champlain. (Image credit: Supriya Manot)

Waterbury

Waterbury is an historic and artsy enclave closer to Boston and the Green Mountains than Burlington. It’s home to several iconic food and drink brands you may have heard of – Green Mountain Coffee, Ben & Jerry’s, and Cold Hollow Cider Mill.
Waterbury also has plenty to do for a small town in the middle of Vermont. There are mountain bike trails for cycling enthusiasts.  The Waterbury Arts Fest is a two day street festival in July celebrating local artisans. Waterbury also has a happening craft beers scene and there’s lots of great restaurants to go along with the beer too. If you are a coffee lover, visit Green Mountain Coffee Visitors Center at the Historic Waterbury Train Center. Ben & Jerry’s does half-hour factory tours as well as a fun flavor graveyard where you can find retired flavours.
When you are in Waterbury, stay at the colorful Grunbuerg Haus Inn & Cabins which will transport you to the Austrian Alps. It’s not the only Austrian hotel in the area – there’s also the Trapp Family Lodge in nearby Stowe, Vermont (owned by descendants of the von Trapp family of Sound of Music fame).
barn in Waterbury Vermont
For weekend trips, New England towns don’t come much cuter than Waterbury Vermont.

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15 places to visit in New England in Summer
15+ places to visit in New England in Summer Summer Vacation | Maine | Connecticut | New Hampshire | Vermont | Massachusetts Travel Destinations | Honeymoon | Backpack | Backpacking Vacation | Budget | Wanderlust | Off the Beaten Path #travel #honeymoon #vacation #backpacking #budgettravel #offthebeatenpath #bucketlist #wanderlust #Massachusetts #USA #America #UnitedStates #visitMassachusetts #TravelMassachusetts #discoverMassachusetts #familytravel #Vermont #Maine #Connecticut #New Hampshire

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