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Best Weekend Getaways from Boston: Part One

Summertime in New England is rapidly approaching. As more and more places begin re-opening, the time to plan incredible weekend getaways from the Greater Boston area is now. We’ve rounded up a few of our favorite drivable destinations to inspire your next trip. 

Beacon, New York (~3 hours by car)

Beacon, NY best weekend getaway from boston

Known as a creative haven in the Hudson Valley, the town of Beacon, New York is chock full of contemporary art installations and scenic views of the Hudson River. Take advantage of the complimentary Beacon Bus Loop for a free tour around town or grab a camera and take the trek to Beacon Overlook. 

Where to stay in Beacon: 

Experience country life at the Beacon Hermitage—a quaint bed and breakfast located four miles from Beacon’s Main Street. Take in the silence or explore the nature trails and nearby waterfalls. 

What to do in Beacon: 

Check out the bustling Main Street full of quirky shops, art galleries, cafes, and restaurants. Dia Beacon is a well-known contemporary art museum featuring works from the 1960’s to now and attracts thousands of visitors annually. Looking to unleash your inner artist? Hudson Beach Glass offers tourists a wonderful gallery to explore and glassblowing workshops. 

Where to eat in Beacon: 

Head over to The Pandorica—a Dr. Who-themed restaurant—and split a plate of Satan’s pit of pierogies. Looking for something light? Check out Bank Square Coffeehouse and fuel up on homemade maple bacon apple muffins.  

Block Island, Rhode Island (~3 hours by car + ferry)

Block Island best weekend getaway from boston

Off the coast of Little Rhody lies beautiful Block Island. With over 17 miles of beaches and 30 miles of hiking and walking trails, this tiny-but-mighty destination is perfect for a weekend getaway from Boston. Pro tip: planning on bringing your car across the ferry? Book your tickets in advance.

Where to stay on Block Island: 

The Inn at Ballard’s offers visitors access to a private beach (complete with cabana rentals), oceanfront tiki bars, and a variety of dining and overnight accommodations to choose from. Located a few steps from the ferries, Ballard’s makes any Block Island vacation convenient.

What to do on Block Island: 

Check out the farmer’s market open seasonally between 9:00am and 11:30am (rain or shine) on Wednesdays and Saturdays or take the 141-stair trek to Mohegan Bluffs for views you won’t regret. Feeling adventurous? Book a tour of the whole island by helicopter or horseback. 

Where to eat on Block Island:

Chow down on fresh seafood while enjoying the views from Dead Eye Dick’s or grab a lobster roll from the island’s best-known food truck: Southeast Light Delights. Looking for a cozy dinner date spot? Head over to Kimberly’s and take advantage of their substantial wines-by-the-glass menu options and family feel. Also worth mentioning is the 1661 Inn which offers two fantastic restaurant options: one focusing on breakfast for a cool $40 per person (hotel guests receive a discounted price) and the other showcasing a full sushi bar and incredible views of the Great Salt Pond. 

Mystic, Connecticut (~2 hours by car or ~90 minutes by Northeast Regional train)

Mystic Connecticut Best Weekend Trip from Boston

Once known as a ship-building capital, Mystic is a quaint waterfront town perfect for escaping city life. Accessible by car and train from Boston proper, this charming village is home to an incredible aquarium and seaport district. Fun fact: the 1988 movie Mystic Pizza was inspired by film writer Amy Holden Jones’ trip to Mystic, Connecticut. 

Where to stay in Mystic: 

The Whaler’s Inn offers overnight visitors a taste of history and a central location. Check out their hotel packages if you’re looking to add a romantic flair to your stay. Lovers of peace and quiet can book a room at the Mermaid Inn; a quaint bed and breakfast owned and operated by a local artist. 

What to do in Mystic:

Check out the nationally renowned Mystic Maritime Museum filled with local folk art, boat exhibits, and ships—some are even rentable! Head over to Adventure Mystic for an assortment of kayak, boat, snowboard rentals or purchases. Classes and lessons are also available for a variety of sports and activities.  Whale watching tours are readily available during migration season and Mystic is home to several stunning and historical lighthouses.

Where to eat in Mystic: 

Grab a slice from the original Mystic Pizza location on West Main Street or jump timelines and order breakfast from Somewhere in Time Cafe.  Prefer a casual sit-down dinner date spot for two? The Captain Daniel Packer Inne Restaurant & Pub is a great choice with an English pub-influenced menu and creative libations.  

Montreal, Quebec, Canada (~5 hours by car)

Montreal Mont Royal

Grab your passport and take the scenic route up to Montreal, Canada for a weekend away. Filled with plenty of green spaces, cultural and historical sites, and a killer food scene, Montreal is the perfect place for city slickers, families, and couples alike. Stroll along the cobblestone streets in Old Montreal taking in the sights, sounds, and scents of Europe without leaving North America. Fun fact: Montreal has more restaurants per capita than any other Canadian city. 

Where to stay in Montreal: 

Visitors will find plenty of recognizable hotel chains located between the neighborhoods of Quartier Concordia and Gay Village such as the Intercontinental: Montreal, Courtyard by Marriott Montreal Downtown, and the Fairmont Queen Elizabeth. Travelers looking for a more local (and budget) experience should consider the Airbnb options available—many include parking. 

What to do in Montreal: 

Head to Mont Royal park for incredible views of the city. Accessible year round, this lookout point is the perfect place for leaf peepers, snow shoeing, and photo opportunities. Walk or train to the Jean Talon farmer’s market, open seven days a week with vendors selling local cheeses, artisanal meats, and ice wine. Museum junkies have a variety of options to choose from such as the Montreal Museum of Fine Arts, the Montreal Museum of Archeology and History, and Saint Joseph’s Oratory.   

What to eat in Montreal:

No trip to Montreal is complete without a smoked meat sandwich from Schwartz’ Deli. With take-out and sit-down options, this Canadian classic is an absolute must! La Banquise operates 24/7 and has over 20 types of poutine available—perfect for a late night snack or hangover cure. Diners seeking a French bistro atmosphere should head over to L’Express; a centrally-located hot spot with an authentically-French menu and European decor.

White Mountains, New Hampshire (~2.5 hours by car)

white mountains new hampshire best weekend getaway from boston

Located at the northern end of the Appalachian Mountains and covering New Hampshire and Maine lies the stunning and rugged White Mountains. While there are several towns with easy access to this stretch of summits we love Conway for the convenience factor, shopping outlets, and unlimited year-round activities. Don’t forget your camera!

Where to stay in the White Mountains: 

Red Jacket Mountain View Resort (also home to Kahuna Laguna Water Park) is a family-friendly full-service resort sprawled across over 40 acres of land. Almost every guest room and suite comes with mountain views from private balconies. The budget-friendly Red Elephant Inn Bed & Breakfast is another fantastic choice for accommodations near Conway. With a 5/5 ranking on TripAdvisor, the Red Elephant includes free parking, free breakfast, and a central location to many restaurants and hiking trails. 

What to do in the White Mountains: 

Get a closer look at Mount Washington by taking the 7.6-mile Auto Road and scope out the highest mountain peak in the Northeast. Prefer sitting back and taking in the views? True to its name, the Conway Scenic Railroad offers a variety of tours-by-train ranging in length from one hour to nearly six hours. With waterfalls (Diana’s baths), picnicking spots, hunting, and a nearby indoor water park (Kahuna Laguna Water Park), Conway and the White Mountains have something for everyone. 

Where to eat in the White Mountains: 

Vito Marcello’s Italian Bistro (formerly Bellini’s) combines a charming setting with authentic Italian cuisine. Reservations are recommended as Vito Marcello’s is only available for dinner. With an award-winning restaurant, meals to-go, cider tastings, and weekend rotisserie selections, the White Mountain Cider Company is a great stop on any traveler’s itinerary. Closed on Tuesdays and Wednesdays. 


What are your favorite weekend getaways from Boston?