7 Perfect Destinations For A Long Weekend In New England
The beauty of traveling in New England is how easily one great weekend can lead to another. Within just a few hours, you can go from skiing near Great Barrington in the Berkshires to sampling freshly caught lobster in coastal Maine, or wind up stargazing in Charlestown, Rhode Island, before calling it a night. If you would rather spend your getaway immersed in culture, the region also makes it easy to fit in an art museum, live concert, or comedy show without going far. So go ahead and clear a spot on your calendar, because one of these towns is bound to become the highlight of your next weekend escape.
Great Barrington, Massachusetts
If you find yourself in the Southern Berkshires, you have to check out Great Barrington. It is one of those spots that you can visit no matter the weather, thanks to its ski slopes, hiking trails, and a great performing arts scene. With the winter season still underway, you can spend a day or two at Ski Butternut, a ski area with 100 skiable acres and 22 ski trails to explore. The summer, meanwhile, brings hikes like Monument Mountain, a 1,642-foot peak that over 20,000 hikers ascend each year. Throughout the year, the Mahaiwe Performing Arts Center puts on comedy shows, dance performances, live concerts, lectures, and more. To round out your weekend, you can spend the night at the Graville House, a cozy bed-and-breakfast set in a former residence dating back to 1825. In fact, the cozy B&B earned a Michelin Key in the 2025 Michelin Guide!
Charlestown, Rhode Island
Nicknamed “the best kept secret in Rhode Island,” Charlestown is lined with miles of secluded beaches, along with more distinctive attractions like an operational observatory. If you want to start your weekend at the beach, you can head out to East Beach, which is one of the least developed beaches in the state. For some souvenir shopping in the afternoon, stop by the Fantastic Umbrella Factory, an artisan shopping center that sits on an old farm homestead, selling gifts, block prints, Native-made crafts, candy, and toys. As night falls, prepare for an evening of stargazing at the Frosty Drew Observatory, which is open on Friday nights and for special events. The General Stanton Inn will be ready to welcome you afterward, which was established back in 1740. Undergoing renovations in 2022, the rooms today are split between colonial style and more modern atmospheres.
Kennebunkport, Maine
Kennebunkport sits between the Kennebunk River and the Atlantic Ocean, offering kayaking excursions, ice skating, and a particularly notable culinary scene. Travelers hoping to explore the river can arrange a rental with Kennebunkport’s Kayak Excursions, a trusted agency in town that has been operating since 1995. Depending on how much time you will be in town, you can rent for a half day, a full day, or even a full week. You are also still in time for some winter fun at The Waterhouse Center, which hosts a large ice rink from November through March. From June through October, travelers can explore the food scene with a lunchtime walking tour from Maine DayVentures. Samplings during the tour include bites like fresh lobster straight from the fishing boat, Maine clam chowder, craft beer, and a traditional Maine “Whoopie Pie." The Colony Hotel has one of the best hotel views in the entire town, overlooking the Atlantic with a private beach.
Madison, Connecticut
Madison is a small town along the Connecticut shoreline with a lovely mix of beaches and preserves for a weekend of outdoor fun. Hammonasset Beach State Park is the perfect place to begin your recreation, featuring two miles of sandy beaches, a nature preserve, and a campground. For some mountain biking or hiking, Rockland Preserve is a great option, featuring paths that wind along rocky cliffs, ledges, and wooded areas. For some memorable seafood, you can grab dinner at The Wharf, a waterfront restaurant that is located inside the Madison Beach Hotel. Travelers can either opt to spend the night at the same hotel or lodge at The Homestead Madison if they are craving something a little bit more quaint. This boutique bed and breakfast has been family-owned and operated for three generations, set in a home built in 1958.
Manchester, Vermont
Vermont’s Green Mountains are iconic for weekend getaways, and Manchester might just be the best town in the whole range. This town is just a short drive from several ski resorts, such as the Bromley Mountain Ski Resort, a beloved ski area that overlooks the mountains with 47 trails and nine lifts. When the weather warms, head to the Lye Brook Wilderness to hike the Lye Brook Falls Trail, a 4.5-mile trail that leads to a 125-foot waterfall. Or check out art at the Southern Vermont Arts Center, which showcases works by local, national, and international artists. Once you have finished exploring for the day, you can unwind at the Inn at Manchester, an adorable inn that sits on four acres of rolling land, divided into 21 well-decorated guest rooms.
Gorham, New Hampshire
If you appreciate forests and wildlife, you will love visiting Gorham. Located in the Androscoggin Valley, within the White Mountains region, this little town has developed a reputation for its moose tours, offered through Gorham Moose Tours. These tours have between a 93% and 97% success rate, giving you a pretty good chance of spotting the majestic creature. You can also spend a day at Moose Brook State Park, which is popular for fishing, camping, and swimming in a natural pool fed by fresh mountain water. The Three Sisters Gallery is a wonderful place to view art and take classes offered throughout the year. Travelers can check into the Top Notch Inn at the end of the day, which offers amenities such as a heated pool, hot tub, stone fire pit, cornhole, grills, and more.
Northampton, Massachusetts
Northampton has received multiple recognitions for its art scene over the years, and a weekend is just the right amount of time to explore its highlights. Make sure to take a look at the Academy of Music calendar before your visit, which puts on a wide range of shows throughout the year, ranging from storytelling and comedy performances to puppet shows and film screenings. You will also find a fascinating selection of art at the Smith College Museum of Art, which exhibits pieces from the ancient era through modern times. For some exercise, grab your bike or running shoes and head to the MassCentral Rail Trail. This trail begins in Northampton and will eventually stretch 104 miles to Boston once it is completed. Finish the day out at the Ellery Hotel, which lies on the edge of Smith College, featuring renovated rooms and a complimentary light breakfast in the morning.
A Region With So Much To Discover
New England is chock-full of places to discover, making it quite difficult to narrow down the choices at times. However, these seven towns are great ones to keep in mind as you plan your next long weekend, thanks to their diversity of activities. Some of them, like Madison, offer the ultimate beach vacation, while others, like Gorham, really explore the area’s native wildlife. No matter which itinerary you decide to go with, you are bound to have a memorable time!
