Top 10 Weekend Getaways From Boston

Our research is editorially independent but we may earn a commission for purchases made through our links.

While Boston is a great city to be in, occasionally you’ve got to make an escape, and a day trip may not be enough. Fortunately, you’ve got a myriad of options when it comes to great weekend getaways. From beach retreats to mountain escapes, you’re sure to find just what you’re looking for among this list.

Provincetown and the Cape Cod National Seashore, Massachusetts
Cape Cod, Massachusetts

Provincetown and the Cape Cod National Seashore, Massachusetts

The Cape Cod National Seashore is a 40-mile stretch of beautiful dunes and picturesque lighthouses. Provincetown, on the northern end of the Cape, is just a two-hour drive from Boston and hosts a colorful downtown lined with grand mansions, fine dining restaurants and tasty seafood shacks, art galleries and interesting shops. It’s a great place for people watching and offers a wide range of activities, from beach walks to hiking, biking, swimming and fishing. Tour one of the five historic lighthouses that are open to the public, or take a whale watching tour to watch for humpback whales, seals, dolphins and other marine life.

Martha's Vineyard, Massachusetts
Oak Bluffs Beach, Martha's Vineyard

Martha's Vineyard, Massachusetts

Martha’s Vineyard is a popular weekend getaway for many East Coast residents, and Bostonians are lucky to have it practically at their doorstep, a ferry ride away from Falmouth. The storybook town of Oaks Bluff on its northeastern shore with its vibrantly-painted gingerbread cottages is also home to beaches that face Vineyard Sound making it ideal for swimming with very minimal surf. Visitors can also enjoy rides on the oldest carousel in the country – the Flying Horses Carousel has been spinning since 1876.

Newport, Rhode Island
The Breakers, Newport, Rhode Island

Newport, Rhode Island

Newport is one of the country’s top spots for sailing, but it offers a whole lot more to do on a weekend escape from Boston. Touring the Newport mansions is a must-experience, including The Breakers, a National Historic Landmark that’s arguably the most magnificent and famous of them all. A symbol of the Vanderbilt family’s social and financial preeminence during turn-of-the-century America, it was built as a summer home for Cornelius Vanderbilt II in 1893 and has over 65,000 square feet of indoor space along with a perfectly manicured 13-acre lawn overlooking the Atlantic.

Nantucket, Massachusetts
The beautiful Nantucket shore

Nantucket, Massachusetts

Nantucket Island sits 30 miles off the coast from Cape Cod, accessed by ferry. It offers lots to enjoy on a relaxing weekend, from beautiful beaches and grand mansions to fine dining, outstanding shopping, lighthouses and a whaling museum that features the skeleton of a 46-foot-long bull sperm whale that came ashore on a beach here in 1998. When you want to get active you’ll find multiple paths that branch off in every direction for hiking or biking. History buffs won’t want to miss exploring the historic district with its over 800 pre-Civil War houses.

Kennebunkport, Maine
Kennebunkport, Maine

Kennebunkport, Maine

This southern Maine seaside town is a 90-minute drive north of Boston, located along the Kennebunk River about a mile from its mouth on the Atlantic. It’s famous for Dock Square, which hosts a variety of local craft shops that sell everything from hand-crafted jewelry to souvenir t-shirts. You’ll also find a diverse array of eateries like legendary mouth-watering lobster served at Mabel’s Lobster Claw Restaurant. Enjoy boating excursions, including whale watching tours and lobstering adventures where you can step into the shoes of a real-life fisherman and even pull up a lobster trap. You can also head out onto the water on your own by renting a kayak, canoe or kayak.

Stowe, Vermont
Stowe, Vermont in the fall

Stowe, Vermont

Located three hours from Boston, Stowe is popular for skiing in the winter, but in the warmer months you can enjoy some of the region’s best hiking, golfing, mountain biking, kayaking, swimming and scenic drives. In autumn it’s absolutely bursting with color. But its appeal lies beyond the mountains as the village itself is postcard perfect, with covered bridges and church steeples set against the Green Mountains. Stock up on made-in-Vermont items like cider donuts and maple syrup, and catch a show at the Stowe Theatre Guild which hosts entertaining musicals.

Bretton Woods, New Hampshire
Mount Washington National Park in Bretton Woods

Bretton Woods, New Hampshire

Just a little over two-and-a-half hours from Boston, Bretton Woods hosts New Hampshire’s largest ski area, and also offers lots to do during the warmer months of the year. One of the most popular attractions is “The Cog.” The Mount Washington Cog Railway runs both steam and biodiesel-powered locomotives that climb 3,500 feet or so up to the highest summit in New England at 6,288 feet. From here, you’ll enjoy panoramic views that span the valleys and mountains of New Hampshire, Maine, Vermont, Canada and the Atlantic.

Portland, Maine
lighthouse on the coast, Portland, Maine

Portland, Maine

Portland, Maine offers city delights with small-town charms and the opportunity to enjoy all sorts of recreational activities. It hosts a stretch of the Appalachian Trail for scenic hikes along with opportunities for biking, swimming and every type of paddling you can think of. After a day of play, you can look forward to indulging in one of the country’s top food scenes. New restaurants seem to pop up every week, and there are countless award-winning options here.

Portsmouth, New Hampshire
Portsmouth, New Hampshire

Portsmouth, New Hampshire

Portsmouth is only a few hours from Boston but it feels like it’s world’s away. This historic seaport offers beaches, parks, beautiful gardens and a fascinating indoor/outdoor living history museum. The Strawbery Banke Museum traces the town’s earliest history which dates back to 1623 as one of the oldest in America. Step back in time for a glimpse into centuries past through restored homes from four different centuries and work artisans who illustrate New Englanders’ lives in the early years.

Sturbridge, Massachusetts
Sturbridge Living Museum, Sturbridge, Massachusetts

Sturbridge, Massachusetts

Just an hour from Boston is the beautiful town of Sturbridge Old Sturbridge Village, a living history museum where you can step back in time to the early 19th-century, exploring authentic homes, a general store, schoolhouse, pottery shop, tavern, sawmill, barns, church and more.

You May Also Like
12 Best Resorts in Maui for Couples

Travel Deals

8-Day Active & Discovery Danube River Cruise


Fiji: Your Easy Island Escape w/ Nonstop R/T Flights


9-Day South Africa Safari Cruise w/ Luxury Lodge Stay


27' Coachmen RV Apex Ultra-Lite 245BHS


Vail | Book Direct for Best Rates + Cash Back Rewards


Air & 13-Day Australia Cities, Wilderness & Wildlife Safari


Ace Hotel New Orleans | Up To 35% Off


33' Coachmen RV Pursuit 33 BH


Air & 6-Day Colombia & Peru Vacation


Air & 9-Day Australia: Sydney, Great Barrier Reef & Wildlife


The Westin Las Vegas Hotel & Spa | Save On 5 Nights


12-Day Brazil to Peru Tour w/ Domestic Flights


10-Day Northern Europe | Pick Your Perk


25' 2008 Four Winds RV


Air & 11-Day Dundee's Awesome Adventure Tour