10 Best Weekend Trips From Boston, Massachusetts - Updated 2023

weekend getaways from boston

Covering over 49 square miles (127 square kilometers) and having a population of nearly 700,000 people, Boston is known to be the biggest city in the Commonwealth of Massachusetts. It has become famous for its innovations in art, music, sports, and technology. A constantly thriving and developing city, Boston has become a popular tourist destination for travelers around the world and around the country. There are a lot of places to visit and things to do in the city, including shopping, picnicking, strolling, visiting museums and heritage streets, photography, and food trips. It is also in a convenient location, so once you’ve toured Boston, you can head to other nearby cities and towns for the weekend. It can be overwhelming to choose what to do, so to help you out, check down below for our picks for the best weekend trips from Boston, Massachusetts to add to your itinerary.

1. Cooperstown, New York

Cooperstown Street
Source: Photo by Wikimedia Commons user Marcbela used under PUBLIC DOMAIN

With scenic views of the lakes and mountains, Cooperstown is 376 kilometers (234 miles) away from Boston and is a popular place to do outdoor activities such as biking, hiking, ice fishing, and skiing. The area is popularly known for sites like National Baseball Hall of Fame and Museum, Otsego Lake, Cooperstown Dreams Park, Lake Front Park, and Heroes of Baseball Wax Museum. With a wide array of inns and bed and breakfast properties available, this is an easy place to explore and a great location to experience the more forested side of New York.

2. Portland, Maine

Docks in Portland Maine - August 2008
Source: Photo by Wikimedia Commons user Stilfehler used under CC BY-SA 1.0

Having a growing population of over 66,000 people, Portland is the most populous city in the state of Maine and is 183 kilometers (114 miles) away from Boston. People who love art, history, and food will love the experience of visiting this metropolis. It is filled with many parks, historical sites, gardens, and award-winning restaurants. Specializing in the service sector and tourism to gain funding, Portland is a popular place with many tourist attractions such as Victoria Mansion and Portland Museum of Art. The city also hosts numerous events throughout the year, such as the Old Port Festival, Seaweed Week, and Love Fest.

3. Brandon, Florida

Source: Photo by Wikimedia Commons user FightingRaven531 used under PUBLIC DOMAIN

Brandon is a suburban area of Tampa and is rated as one of the best places to live. It is 260 kilometers (162 miles) away from Boston. The area offers so many recreational activities that families will love doing, such as golfing, shopping, trying out escape room adventures, visiting museums and exhibits, going indoor skydiving, and more. Some of the most popular attractions that you might want to consider visiting include Dinosaur World, Wat Thai Temple, Tampa Bay Grand Prix, and Eureka Springs Park. The place is also abundant with natural sites like parks and lakes.

4. Provincetown, Massachusetts

Provincetown Harbor Coastline
Source: Photo by Wikimedia Commons user Jacob Beach used under CC BY-SA 4.0

Only 90 kilometers (56 miles) away from Boston and located at the tip of Cape Cod in Barnstable County, Provincetown is a place surrounded by water. Experience the pleasant feel of stepping on the white sand shores of Provincetown as you enjoy the fresh breeze coming from the ocean. The place celebrates individuality and freedom of expression, and it is a place that is very LGBT-friendly, even known as “the Gayest City in America”. Tourist attractions that you should try to visit and explore are Pilgrim Monument, Herring Cove Beach, Race Point Lighthouse, Long Point, and Provincetown Art Association and Museum.

5. Peterborough, New Hampshire

Peterborough, New Hampshire
Source: Pixabay

Located on nature’s doorstep, Peterborough is 101 kilometers (63 miles) away from Boston and is a popular destination for people who like the outdoors and going on adventures. The place is filled with many great trails, parks, lakes, heritage spots, and sports and wellness centers. Enjoy the magnificent views of the jagged mountains, valleys, and unique lakes as you spend your time hiking, camping, or fishing. Some of the recommended areas you should visit include Greenfield State Park, The MacDowell Colony, Temple Mountain, and Nubanusit Lake.

6. Providence, Rhode Island

Downtown Providence, Providence, RI, USA - panoramio
Source: Photo by Wikimedia Commons user LEONARDO DASILVA used under CC BY 3.0

Providence is 69 kilometers (43 miles) away from Boston and is the most populous city of Rhode Island. It is a place with many business establishments, historical buildings, and beautiful views of magnificent rivers, skylines, and city lights. If you love partying, shopping, street photography, and art, you’ll love visiting this destination. Some of the top attractions in the area are RISD Museum, Benefit Street, and Waterplace Park.

7. New Haven, Connecticut

Harkness Tower, Yale University, New Haven CT
Source: Photo by Wikimedia Commons user John Phelan used under CC BY-SA 3.0

With a growing population of 130,000 people, New Haven is the second-most populous city in Connecticut and is 223 kilometers (139 miles) away from Boston. The place is popularly known as the home of the prestigious Yale University. It also has historic sites, museums, and beautiful Victorian architecture. This is the place where many great inventions were made, like vulcanized rubber, Winchester repeating rifle, and sulfur matches. Some of the popular attractions that you should consider visiting are East Rock Park, Lighthouse Point Park, It Adventure Ropes Course, and New Haven Green.

8. Newport, Rhode Island (from USD 135.0)

112 kilometers (70 miles) away from Boston, Newport is a seaside city in the famous Rhode Island. The place is known for its colorful history, old historic buildings, its overall spectacular scenery, and being given the title of “Sailing Capital of the World”. Visiting the island, tourists will have a chance to view the summer homes of several important families such as the Rockefellers, the Vanderbilts, and the Astors. While here, try out some of the best cuisines in America and enjoy the most beautiful sunset views. Some of the most popular places to visit in Newport include Marble House, The Elms, Cliff Walk, International Tennis Hall of Fame, Fort Adams State Park, and Rough Point.

Newport Mansions from Boston Small-Group Day Trip with Guide

Duration: 11 hours

153 reviews

9. Martha's Vineyard, Massachusetts (from USD 115.0)

A summer colony that is a popular year-round vacation destination, Martha’s Vineyard is an island 140 kilometers (87 miles) away from Boston. Visit the island and be greeted by world-class beaches, farm-fresh food, marvelous views of the sea, and a quiet and relaxing environment. Some of the top attractions on the island are Joseph Sylvia State Beach, Aquinnah Cliffs Overlook, Cuttyhunk Island, and Moshup Trail. Although separated from the mainland, this is still a place where you can enjoy shopping, and some popular stores you might recognize in the area are Phillips, Lululemon, Lorraine Parish, Laughing Bear, and Lennox & Harvey.

Martha's Vineyard Daytrip from Boston with Round-Trip Ferry & Island Tour Option

Duration: 12 hours

1607 reviews

10. Woodstock, New York

Source: Photo by Wikimedia Commons user HighAtop94 used under CC BY-SA 4.0

Woodstock is 307 kilometers (191 miles) away from Boston and is a place known for its huge support for music and the arts. But at the same time, they deeply value their natural attractions. In 1969, the town refused a permit to host a festival due to concerns of violence and the possibility of destruction of the town’s natural resources. That said, they have many preserved forested areas that everyone can still enjoy today. A few of the popular places in Woodstock include Ashokan Reservoir, and Catskill Center.

Hassle-free trips from Boston

Boston is a popular city with many great tourist attractions, but there are also so many other places near the city that you can visit. Though it can be a hassle to drive to these popular tourist attractions, many transport services allow you to visit other cities or towns so you don’t need to gas up your car. So, pick a place to visit and be sure to enjoy a trip to these best weekend trip destinations from Boston.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Some guy in his early twenties, having a knack for tech, philosophy, and the arts. Jayric Maning is currently busy doing some personal projects while sneaking in some writing on the side and doing...Read more

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