Explore Boston

Hit the Road This Weekend on These Fun Road Trips From Boston

Summer is for vacation and getting away from it all. The coronavirus may have put a damper on where Bostonians can travel this summer but there are lots of getaways within two hours of the city. Discover the Best Roadtrips from BostonCheck out these historical landmarks, beachfront towns, and outdoor excursions to add a bit of fun to summer 2020. Before heading out on an adventure, be sure to don a mask and check the safety restrictions in place at your destination.

In Algonquin, Ogunquit means ‘beautiful place by the sea.’ Just shy of 90 minutes from downtown Boston, Ogunquit lives up to its name with miles of beautiful beaches, scenic coastline, and quaint colonial streets to explore. Take a stroll down Marginal Way, a 3-mile pedestrian thoroughfare along the water that terminates in the cute fishing village of Perkins Cove. This is an excellent place to go shopping in one-of-a-kind boutiques, enjoy lunch along the waterfront, or watch the manually operated drawbridge move for boat traffic. Swimming, kayaking, and kite flying are just a few ways to pass a day on the white sand beaches. Watch the lobster boats come and go; some boats even offer tours for visitors to get a look at how it’s done. 

(©James Kirkikis/Shutterstock)

In less than an hour, Bostonians can step back in time. Plymouth is the one of the oldest settlements in the United States and the oldest in New England. The historic Plymouth Rock is said to be where the pilgrims originally landed in late 1620. The glacial boulder that marks the site is now housed in a columned portico on the shore. Nearby, a replica of the Mayflower floats in the harbor. There are also plenty of memorials and statues commemorating a variety of historical figures and fallen soldiers throughout Pilgrim Memorial State Park. Take a tour with some of the world’s oldest and largest cranberry growers (A.D. Makepeace Company and Cape Cod Cranberry Growers Association) located in Plymouth. They’re promoting the economic viability of small growers and are dedicated stewards of the land. The food scene is surprisingly eclectic (outdoor seating and take out available). Gourmands can nosh on lobster rolls or explore the menus at trendier, modern bistros.


Many visitors to Salem, Massachusetts already know about its spooky past and the witchcraft trials of the 1690s. Several museums dedicated to the trials are open for visitors including the Salem Witch Museum, the Witch House (the former home of Judge Corwin, one of the judges involved in the trials), and the Witch History Museum. After learning about the omens that condemned the young women during the trials, visitors can try their luck with modern-day psychics and get a tarot or palm reading at Crow Haven Corner. Salem is more than witchcraft and sorcery. Charlotte Forten Park, Salem’s newest green space, is a 25,000 square foot park named after the abolitionist and Salem State’s first African American graduate. It’s the perfect place to lounge in the sun, stroll along the waterfront, or take in an impromptu musical performance. The park is directly connected to the downtown area making it easy to get to favorite shops and restaurants.

(©LnP images/Shutterstock)

Old Orchard Beach is a nostalgic trip down memory lane to the beach vacations of yesteryear. Seven miles of beach is bordered by an old fashioned boardwalk alive with arcades, restaurants, carnival games, and folks fishing off of the pier. Don’t let the wistful ambiance fool you, there are plenty of modern things to do including sailboat or paddleboard rentals and zip lining. The Old Orchard Beach pier looks like something out of a movie. Buildings pop up out of the ocean and seem to precariously balance on a crisscrossing network of stilts. Charter a fishing boat and get a better look at the floating structure before heading out to sea for a day of angling. All of this shmaltzy beach fun is fewer than two hours from Boston.

(©Dan Hanscom/Shutterstock)

For those still trying to safely avoid crowded areas, try taking a hike up Mount Monadnock. The state park of the same name is 2 hours from Boston and just across the border in New Hampshire. It’s only $5 to get in and parking is included. From the parking lot, there are 3 trails of varying difficulty to the 3,000+ foot summit. On clear days, intrepid hikers can see the Boston skyline from the top of the mountain in addition to the surrounding valleys. Intermediate hikers should consider taking the White Dot Trail (which is a bit steeper and rockier) to the top and then follow the White Cross Trail back to the parking lot (a much easier way down).