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8 Best Day Trips from Boston

April 30, 2021

We love our dynamic Brighton neighborhood. However, when we need a break from the hustle and bustle of city life, our location couldn’t be more perfect. The Overlook puts you less than a 2-hour drive from some of the best day trip destinations in New England. We’ve listed several recommendations, perfect for a quick getaway.


Portland, ME

With cobblestone streets and picturesque lighthouses, Portland, ME has everything you could want in a small New England town. From boutiques and art galleries, to quaint pubs and charming cocktail bars, there’s so much variety. Not to mention, their eclectic food scene is top-notch. Try out restaurants owned by some of America’s award-winning chefs. The best part? It’s a 2-hour drive from The Overlook.


Ogunquit, ME

Feeling artsy? Head just a 1.5-hour drive up to Ogunquit, a popular beach town on the breathtaking coast of Maine. This destination includes an array of artistic attractions. Check out The Ogunquit Museum of American Art, which highlights over 3,000 pieces of work from the late 1800s to the present. Wander through the eye-catching galleries around town, like The Barn Gallery or Sea Bell Gallery. You can also catch a show at the Ogunquit Playhouse.


Portsmouth, NH

Once a major seaport and naval center, Portsmouth is home to some intriguing American history. Explore Albacore Museum, a tourable Cold War-era submarine, and the Strawbery Banke Museum, a 10-acre, outdoor museum that features historic buildings from the 17th and 18th-century. Portsmouth also offers an upscale shopping and dining experience along Market Street and Congress Street.


Cape Cod’s Shining Sea Bikeway

Looking to go on an adventure with your bike? Cape Cod’s well-known Shining Sea Bikeway is a 22-mile trail that begins just over an hour drive from The Overlook in North Falmouth. Built on the remains of the Old Colony Railroad, this trail winds along the picturesque Vineyard Sound Shoreline. Pass through some cranberry bogs, a few charming Cape Cod-style houses and a stunning beach before reaching the end.


Northampton, MA

Attracting tourists from all over the country, Northampton is a hip, artsy town that’s just under 2 hours from The Overlook. Head out for a day of kayaking along the Connecticut River. Make sure to grab a coffee from one of their local cafes on the way. You can also enjoy a day of shopping at the popular Thorne’s Marketplace, a three-story mall that’s home to charming, local boutiques and shops, including a candy store and a natural wellness market.


Newport, RI

The best thing to do in the charming seaside city of Newport is going for a peaceful stroll along their famous Cliff Walk, a 3.5-mile oceanside trail that offers refreshing sea breezes on one side and gorgeous sights of Gilded Age mansions on the other. When you’re done with your walk, head over to Marlborough Street for lunch at the White Horse Tavern, also known as the oldest operating restaurant in the U.S. Just under a 2-hour drive from The Overlook.


Providence, RI

In the mood for a major food tour? Located about an hour away from The Overlook and home to Johnson Wales University’s College of Culinary Arts, Providence is filled with kitchen talent, making it a food lover’s dream. The city’s downtown neighborhood is known for its must-try seafood restaurants, Federal Hill is loaded with impressive Italian eateries and shops, and Yoleni’s is a 40,000 square-foot Greek market that serves up authentic dishes and over 800 different artisanal goods.


Lexington, MA

No car? No problem! The best part about taking a day trip to Lexington is that it can easily be done on two wheels! Grab your bike and cruise about 12 miles along the Minuteman Bikeway, which begins in North Cambridge and runs right through Lexington. This vibrant town is known for their historic landmarks from the Battle of Lexington, and their array of local mom and pop shops.


When you’re ready to escape, our ideally located Brighton apartment community puts you close to it all. Let’s hit the road!

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