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Portland Head Light on a sunny summer day with flowers in the foreground

17 Fun Weekend Getaways from Boston

Boston is truly one of the best cities in the United States. It’s located right on the east coast and is filled with some of the most amazing restaurants and photo spots on the east side of the Mississippi River. However, everyone needs a getaway sometimes, and luckily there plenty of fantastic weekend getaways from Boston!

Some places on this list can be visited utilizing public transportation, such as the Peter Pan bus, Greyhound bus, or Amtrak. For the most part, you will need to either have your own car or rent a car for these weekend trips from Boston.

Here are the best weekend getaways from Boston–plus some tips on how to plan your trip!

Note: This blog post was written for Our Escape Clause by former Boston resident Krystianna of Volumes & Voyages. Thanks for joining us, Krystianna!

Two white chairs set up overlooking a blue sky on a New England coast

Boston Weekend Getaway Travel Tips

Pack for all types of weather.

The Northeast is notorious for having strange and unpredictable weather. This year, there was a random snow day in May, and sometimes it will randomly be really warm in the middle of November.

For the most part, you’ll want to pack for the season, but don’t be afraid to also pack layers because you genuinely don’t know what you’re going to get.

Harbor of Kennebunkport Maine, one of the best weekend getaways from Boston

Be prepared to make stops along the way!

There are so many great places to visit in the northeast, and you will most likely pass by some of these spots along your drive. Try to plan on pulling off at least a few times during your ride to or from your destination if you’re driving a car.

Especially if you’re heading up to Vermont or Maine, you’re going to pass by some epic viewpoints driving from Boston.

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Rental car prices can vary dramatically depending on pickup location.

Don’t just rent from the first rental car place that you find. Instead, be sure to check out other rental car options in the area, including Boston’s suburbs. You might be surprised at the deals you’ll be able to find.

Need to rent a car for your getaway? We recommend shopping with Discover Cars! They’ll compare prices and inclusions from multiple brands to ensure you’re getting the best deal for your trip.

Curving road surrounded by fall foliage in New England, as you'll see during fall road trips from Boston MA!

The Best Cities for Weekend Getaways from Boston

Portland, Maine

Nestled on the coast of southern Maine, Portland is one of the easiest weekend getaways from Boston and is a classic New England getaway.

While you’re there, be sure to stroll around the Old Port, admire Portland from above at the Portland Observatory, snap photos at the Portland Bug Light, tour the beautiful Victoria Mansion, and visit a few of Portland’s famous breweries.

And, of course, you can’t visit Portland without heading out to John Williams Park and admiring the famous Portland Head Light for yourself!

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Distance from Boston

1 hour, 45 minutes by car or 2 hours, 30 minutes by train.

How to Get to Portland from Boston

While driving is the easiest way to visit Portland (you’ll have more options for exploring and day trips while you’re there, there are also direct trains between Portland and Boston, making this one of the best Boston weekend trips for travelers who don’t want to drive.

Portland Bug Light as seen from the side with a sailboat passing by behind it

New York, New York

New York City is America’s most popular city for a good reason: it’s loaded with great things to do! Absolute must-sees for a weekend in New York City include Central Park, the Statue of Liberty, Times Square, and the Empire State Building. Fans of museums and history should also opt to visit the Metropolitan Museum of Art or the Modern Museum of Art.

If you’re lucky enough to be visiting during the wintertime, you absolutely must head to Rockefeller Center to see the giant Christmas tree. The Rockettes also perform in the winter months. Be sure even to try to catch a Broadway show, but book your tickets well in advance.

There are lots of great neighborhoods to stay in during your weekend. Just remember that New York City is vast, and the closer to the city center you are, the less you’ll have to spend on transportation, and New York City traffic can be horrendous. Opt to try to stay near SoHo for its charming architecture, Greenwich Village to be in the trendy part of the city, or Brooklyn, which is known for being hipster and upbeat.

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Distance from Boston

4-6 hours.

How to Get to NYC from Boston

The easiest way to get to New York City is to drive, but having a car in NYC can be a hassle!

We recommend taking the Amtrak or the Megabus from Boston’s South Station–the train is a bit more comfortable, and less likely to experience delays due to traffic (a big risk with bus travel between the two cities) but also much more expensive than taking the bus!

Empire State Building or Top of the Rock: Girl with Binoculars on Empire State Building

Burlington, Vermont

Burlington is drastically different from Boston, but that’s what makes it the perfect weekend getaway spot.

This quaint, lakeside city in Vermont is the most populated part of the whole state. However, it only has a population of 43,000 people, with the majority of citizens being college students at Champlain College and the University of Vermont.

One of the best things to do in Burlington is to go to Church Street, which is a marketplace quite like Newbury Street and Quincy Market in Boston. It’s a beautiful cobblestone street lined with areas to shop. Other popular spots include the Ethan Allen Homestead Museum, Waterfront Park, and the Fleming Museum of Art.

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The Ben & Jerry’s Factory is only a short ride away from Burlington, so plan on taking a detour there on your way to Burlington or on your way back to Boston. There are free tours here offered daily, and you honestly won’t want to miss it.

Distance from Boston

3 hours, 15 minutes.

How to Get to Burlington from Boston

It’s most simple to drive to Burlington using I-93 N and I-89 N.

It is possible to take an Amtrak if you have the time, but you have to make a significant detour to New York City since there isn’t a direct route to Burlington, which can take almost a day. 

Sailboats parked on the edge of the lake in Burlington Vermont, one of the best weekend getaways from Boston

Newport, Rhode Island

Just south of Boston is the gorgeous city of Newport, Rhode Island. It’s most famous for its large mansions that are home to many of America’s celebrities, and in many cases, date back to the Gilded Age. One of the best activities to do here is to go on a trolley tour, which will bring you around to many of the area’s best mansions.

Other fun things to do in Newport include swimming and shopping. There’s also the Newport Art Museum, Castle Hill Lighthouse, the Redwood Library and Athenaeum, and Brenton Point State Park. This area is unlike many of New England’s other cities because it really doesn’t feel like a city at all!

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Distance from Boston

1 hour, 20 minutes.

How to Get to Newport from Boston

It’s easiest to travel to Newport car, but you could also hop on two buses (one from Boston to Providence and then Providence to Newport) in under 2 hours.

Mansion in Newport Rhode Island with lawn in the foreground

Best Small-Town Weekend Trips from Boston

Mystic, Connecticut

Mystic, Connecticut, is a quintessential New England town. It’s located right on the water and is breathtaking. There are great views almost everywhere you look. 

Fun places to explore include the Seaport Museum, Misquamicut State Beach, Ocean Beach Park, and the Napatree Point Conservation Area. Honestly, if you’re looking for a small town right on the coast, then Mystic is the place for you!

Distance from Boston

1 hour, 40 minutes.

How to Get to Mystic from Boston

Driving is the simplest way to get straight to Mystic, but you could also take the Amtrak straight from South Station in Boston.

This will only take 1.5 hours!

Historic tall ship in the harbor of Mystic Connecticut, one of the best weekend getaways from Boston ma

Bennington, Vermont

The small town of Bennington, Vermont is located in the southwest corner of the small state, not far from either Vermont’s border with New York or Massachusetts. It serves as the perfect weekend getaway because it’s so vastly different from Boston!

While there, be sure to check out some local restaurants, including Blue Benn Diner, Jensen’s, and Papa Pete’s. There’s also a lovely brewpub called The Tap House, which is fantastic.

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There aren’t a whole lot of places to stay in the town, besides the Hampton Inn. You could opt to stay in one of the bed and breakfasts in the surrounding area of the town. If you’re a fan of the outdoors, be sure to do one of the many hikes in the area, like the hike to the white rocks.

Distance from Boston

2 hours, 50 minutes.

How to Get to Bennington from Boston

It’s easiest to drive here from Boston. It’s possible to take multiple buses, but this can turn into a whole day ordeal.

Historic Henry Covered bridge in Bennington Vermont painted with aging red paint

Manchester, Vermont

Manchester is located only 30 minutes north of Bennington, Vermont, but if possible, it is even more charming! This town is historic and is filled with some of the most beautiful buildings in all of Vermont, and is also a popular place to go shopping. Be sure to check out the Manchester luxury outlet shops and also the Northshire Bookstore.

Similar to Bennington, there are a few hikes in the area that are worth doing, and these ones are a lot less strenuous than other hikes in southern Vermont. 

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Distance from Boston

3 hours.

How to Get to Manchester from Boston

Driving is the only realistic way to get to Manchester from Boston.

Fall foliage along a small street in Manchester Vermonth with a white church visible in the background

Saratoga Springs, New York

Saratoga is a quaint town in New York that is most famous for hosting the Saratoga Races! These occur every summer, so if you’re lucky enough to be visiting during the summer months, then you’ll want to try to go and spend at least one day at the horse races. It’s truly an unforgettable experience.

Other popular places in Saratoga to explore include Saratoga Spa State Park, Saratoga National Historical Park, and the National Museum of Dance & Hall of Fame.

There’s also a really gorgeous shopping area in downtown Saratoga, which is home to the Northshire Bookstore’s New York branch. This bookstore is beautiful and it’s great to support local sellers.

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Distance from Boston

3 hours.

How to Get to Saratoga from Boston

You’ll want to drive to Saratoga from Boston. You could also utilize the bus, but it will take a lot longer.

Historic red farmhouse and cannon near Saratoga NY, one of the best weekend trips from boston MA

Portsmouth, New Hampshire

For a classic, small-town New England getaway complete with historic homes, a beautiful harbor, plenty of seafood restaurants, and a relaxed vibe, you can’t beat the local favorite of Portsmouth, New Hampshire!

While you’re there, visit the popular Strawbery Banke Museum, shop the charming boutiques, explore downtown and the harbor on foot, and enjoy a seafood dinner on the water.

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Distance from Boston

1 hour, 15 minutes.

How to Get to Portsmouth from Boston

You can reach Portsmouth from Boston by either bus or car.

Harbor of Portsmouth NH as seen from across the water. Portsmouth is one of the best weekend getaways from Boston MA

Nature-Focused Boston Weekend Getaways

Acadia National Park, Maine

The first national park east of the Mississippi is absolutely one of the best weekend trips from Boston for those looking for some hikes, some stunning coastal views, and some of the best sunrises and sunsets in New England!

Some of the best things to do in Acadia National Park include watching the sunrise on Cadillac Mountain (during part of the year, this is the first place the sun rises on the continental USA!), strolling around Jordan Pond, hiking the Beehive Trail, checking out the Bass Harbor Headlight, and exploring the Carriage Roads.

Don’t forget to enjoy the charming town of Bar Harbor while you’re there, which is home to great restaurants, a cozy New England vibe, and plenty of beautiful places to stay!

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Distance from Boston

4 hours, 30 minutes.

How to Get to Acadia NP from Boston

The best way to reach Acadia National Park from Boston is to drive. 

While there is a shuttle bus at the park in the summer, it’s vastly easier to visit Acadia with a vehicle.

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North Adams/Berkshires, Massachusetts

The Berkshires are a beautiful region of western Massachusetts that are always highly overlooked and underrated. This area is very rural land is filled with lots of great outdoor activities. This is also the perfect place to go if you are interested in seeing fall foliage.

North Adams serves as the perfect home base for exploring the Berkshires. In North Adams, be sure to check out the Natural Bridge State Park, Windsor Lake, and Cascade Trail.

If it ends up raining a bit while you’re there, don’t worry, there’s also lovely art museums and history museums worth exploring.

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Distance from Boston

2 hours, 40 minutes

How to Get to North Adams from Boston

You can only get to North Adams from Boston by car, but you’ll pass some magnificent scenery along the way!

Cascade Falls near North Adams MA, one of the best boston weekend getaway ideas

Lake Champlain, Vermont

Lake Champlain is a gorgeous lake in Northern Vermont and Northeastern New York. It’s absolutely beautiful and is filled with lots of great outdoor activities, like biking trails, hiking trails, kayaking, canoeing, swimming, and more.

The lake covers a lot of ground, so there are many great towns to set yourself in for exploring the area.

Of course, you could opt to stay in Burlington, but other popular areas to stay include St. Albans and Shelburne. You could also choose to stay on the New York side, such as in Plattsburgh or Champlain. Just know that the prices can drastically change depending on where you opt to stay.

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Distance from Boston

4 hours, 35 minutes.

How to Get to Lake Champlain from Boston

Like most of the outdoorsy places, you do have to drive to get to Lake Champlain from Boston.

bright orange sunset over lake champlain

Kennebunkport, Maine

Kennebunkport is a beautiful town and coastal area in southern Maine. The scenery here is absolutely breathtaking, from the Goat Island Lighthouse to Ocean Avenue. Some popular places to explore here include Gooch’s Beach, Walkers Point, and the Rachel Carson National Wildlife Refuge.

There are lots of more secluded areas around Kennebunkport that you could easily stay in. This makes it perfect for a quiet escape from the city, and ranks it among the best weekend getaways from Boston!

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Distance from Boston

1 hour, 30 minutes.

How to Get to Kennebunkport from Boston

The only way to get to Kennebunkport from Boston is to drive, but you’ll drive right along the coast the entire time! 

4 photos from New England: winding road, covered bridge, portland head light, echo lake. Black and red text on a white background raeds "17 epic getaways from boston"

 

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