10 Best Places To Go For The Weekend Near Boston
Where to Go for a Break Near Boston?
The best places to go for the weekend near Boston are only a few hours away from the city. Thanks to Boston’s geographic position you don’t have to travel far to discover quaint seaside towns, historical New England gems and artsy villages on a weekend escape. Find outdoor adventures and cultural treasures; see where the celebs live and hang out; party on down with a fun LGBTQ crowd and devour some of the best lobster you ever tasted.
Find out more about the best places to go for the weekend near Boston with this guide and enjoy your adventures.
1. Portland, Maine
Historic adventures in Maine’s largest city
Ideal para: Famílias, Alimentação, Aventura
Head north for just under 2 hour’s drive to the largest city in Maine and fall for the charms of Portland with its picturesque lighthouses and thriving craft brewery scene. Stroll the pedestrian-only cobblestone Wharf Street in Old Port, the city’s heritage centre; browse the shops, discover your new favourite cafe and devour the lobster rolls for which the state is famous.
Combine culture with adventure and take to the water on a Maine-built wooden windjammer schooner tour, these stunning boats are listed on the National Register of Historic Places.
Portland, Maine
2. Provincetown, Massachusetts
Art, history and LGBTQ fun
Ideal para: Alimentação, Vida noturna, História
Drive 2 hours south and follow the curl of the coastline around Cape Cod Bay to reach its northern tip and the charming historical seaside town of Provincetown. This is where the Pilgrims landed aboard the Mayflower in 1620 and history buffs can enjoy a deep dive at the town’s museum and Pilgrim monument.
Along with its storied history, Provincetown is also the site of America’s oldest continuous art colony, explore its many galleries and enjoy the town’s creative vibe. At night, P-town, as it’s known by locals, comes alive with its LGBTQ-friendly club scene. Head to Commercial Street for cabarets, restaurants, clubs and more.
Provincetown, Massachusetts
3. Ogunquit, Maine
Sea views and sandy beaches
Ideal para: Casais, Famílias, Alimentação
Drive 90 minutes up the Maine coast to Ogunquit, a peaceful resort town famed for its sandy beaches, thriving arts scene and delicious seafood restaurants. Take a stroll on the Marginal Way, a 2.4-km coastal path connecting Ogunquit to Perkins Cove, to see panoramic Atlantic Ocean views, a picturesque lighthouse and rugged cliffs. Soak up the sun on Ogunquit Beach’s white sand; wake up early, the sunrise here is spectacular.
Join locals in the almost 100-year-old tradition of picking a live Maine lobster from the tank at the Ogunquit Lobster Pound to enjoy cut and cracked with melted butter.
Ogunquit, Maine
4. Watch Hill, Rhode Island
Historic family fun
Ideal para: Casais, Famílias, Alimentação
Cut through Massachusetts on a 2-hour drive south from Boston to Rhode Island’s coastal village of Watch Hill with its beautiful beaches and chances to spot birds and celebrities. Part-time residents include Conan O’Brien and Taylor Swift, who wrote Great American Dynasty about her Holiday Home. There are plentiful ospreys and piping plovers too.
Kids will love riding the Watch Hill Flying Horse merry-go-round, the oldest continuously operating carousel in North America, and everyone will love the St. Clair Annex, a family-owned ice cream shop which opened in 1887. Try a Turtle Sundae with hot fudge, butterscotch, pecans, whipped cream, a cherry and two scoops of house-made ice cream.
Watch Hill, Rhode Island
5. Mystic, Connecticut
Pizza and paddling
Ideal para: Famílias, Alimentação, Aventura
Head straight across the east coast into Connecticut to dive into Mystic’s historic maritime past on the Block Island Sound and explore its New England charms. Don’t miss the Seaport Museum, the US’s largest maritime museum. Inspired by the seafaring past? Paddle the Mystic River on a kayak or hop on board a historic schooner for a guided sunset cruise.
Grab a slice of pizza at Mystic Pizza, the restaurant that inspired the 80s movie starring Julia Roberts, or chow down on the town’s equally famous seafood at one of the many restaurants in the historic downtown waterfront district.
Mystic, Connecticut
6. Kittery, Maine
The gateway to Maine
Ideal para: Compras, História
A 90-minute drive north takes you to York County, Maine where you’ll find Kittery, the state’s oldest incorporated town. With a rich seafaring and military past, you can explore the nearby Portsmouth Naval Shipyard on Seavey’s Island and visit the almost 300-year-old Fort McClary which is one of Maine’s most important historic forts showcasing different modifications for five different wars.
While you’re in Kittery, take a stroll over Memorial Bridge which connects to downtown Portsmouth and offers superb views over the Piscataqua River. Splurge on artisan-made crafts at Wallingford Square at the heart of the Kittery Foreside.
Kittery, Maine
7. Washington, Connecticut
Philosophy, dance and the Gilmore Girls
Ideal para: Famílias, Compras, História
Drive 3 hours southwest from Boston into Connecticut to explore the five quaint ”villages” which make up Washington, an artsy New England gem with a Gilmore Girls connection. The TV show’s creator, Amy Sherman-Palladino, stayed at the Mayflower Inn for two weeks as she brainstormed the cult show which still inspires legions of fans to visit the area to sip coffee like Lorelai and Rory and snap fall-themed photos.
Not a Gilmore fan? Take a walk over the Henry David Thoreau Bridge at the Hidden Valley Preserve and read inscribed quotes from the philosopher-poet. Or groove every July at the Litchfield Jazz Festival or take in a performance from world-renowned modern dance company Pilobolus, based in Washington.
Washington, Connecticut
8. Stockbridge, Massachusetts
Cultural getaway
Ideal para: Casais, Famílias, História
Exploring this picturesque town, a gateway to the Berkshires and Taconic Mountains, a 2.5-hour drive from Boston, is like walking through a Who’s Who of American cultural icons. The Norman Rockwell Museum is here, offering visitors a chance to see the artist’s work and study, Lincoln Memorial sculptor Daniel Chester French had his home here at Chesterwood, and just 10 minutes away, you can take a guided tour of author Edith Wharton’s home, The Mount.
Mix nature with culture on a hike a stone’s throw from Main Street. Cross the wooden footbridge to walk in the footsteps of the area’s famous residents on the trails maintained by the Laurel Hill Association, America’s oldest village improvement society.
Stockbridge, Massachusetts
9. Kennebunkport, Maine
Lighthouses and lobster
Ideal para: História, Foto
A 90-minute cruise straight up the coast from Boston to Kennebunkport offers a weekend of long, sandy beaches, heritage lighthouses and delicious lobster rolls in this popular resort town. Visit Cape Porpoise Pier to get the best views over Goat Island Light Station which was built in 1833.
Year-round the 5 km crescent-shaped Goose Rocks Beach is a must-visit for long sandy walks and superb views over the Atlantic out to nearby Timber Island. Be respectful of the beach house owners and stay off the fragile dune grass.
Kennebunkport, Maine
10. Martha’s Vineyard, Massachusetts
America’s upper-crust vacation spot
Ideal para: Casais, Famílias, História
Take the ferry from the mainland on a 3-hour trip from Boston to the wealthy resort island of Martha’s Vineyard, just south of Cape Cod. Comprised of six towns across 260 square km, Martha’s Vineyard has sandy beaches, farmer’s markets, artisanal stores and plenty of world-class events, including an annual Food & Wine Fair, an International Film Festival and a free-to-the-public Book Festival Summer Series.
Spielberg’s 70’s classic Jaws was filmed here, and although the annual JawsFest no longer happens, you can still take a self-guided tour through the various locations and snap selfies at the real-life Amity at Edgartown.
Martha’s Vineyard, Massachusetts
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