Best Short Road Trips From Boston For Groups

In any season, the noise found on the winding streets of Boston can grow from an idle chatter to a distracting roar. Droves of Celtics fans, which were once endearing and convivial, can become annoying and brash. And with work, school, and maybe a hobby or two to maintain, it can become difficult to maintain closeness with even the best of friends and truest of family.

That’s where a well-timed group trip can be the difference between a burnout-related accidental ghosting and a chance to connect away from the bustle of everyday life. New England is a treasure trove of endless forests, endearing beach towns, and everything in between. The best thing about all these vacation destinations? The best group getaways from Boston are less than a three hour drive away.

Kennebunk and Kennebunkport, ME

A short, hour-and-a-half drive from Boston will have a gaggle of vacationers crossing not one but two state lines to end up in the idyllic town of Kennebunk, Maine and the neighboring seaside community of Kennebunkport.

On the drive up, stop by the Maine Diner in Wells, Maine, of Diners, Drive-ins and Dives fame, for a stack of pancakes and a pick-me-up cup of joe.

To learn more about the historic nature of these seaside towns, try the Haunted Ghost Walking Tour which meet at The Kennebunkport Historical Society. Perhaps you’ll spot the long, white skirts of the famous poltergeist which once appeared over an unmarked grassy knoll in the town. If you’d rather stretch your arms than your legs, grab the group for a half-day kayak rental in Cape Porpoise for a water tour of what’s known as Kennebunkport’s “fishing harbor village.” You’ll be able to spot the signs for lobster rolls from the water.

Indulge in more history with a stay at the Waldo Emerson Inn, built in 1753, where it’s rumored that Ralph Waldo Emerson spent some summers. Or, for a slightly larger group of friends or family, The Cottages at Cabot Cove can provide a quieter, secluded getaway.

Newport, RI

This town on a peninsula, just 71 miles from Boston, offers clear views of the sea and the white sails of boats that dot the ocean landscape.

Driving down to Newport from Boston takes about an hour and a half. Hit the road early so you have time to stop at The Beehive Cafe in Bristol, Rhode Island, a family-owned cafe with a mind for locally sourced food and drink. Order the Honey Pot, a specialty latte with espresso, a milk of choice and (you guessed it) honey.

After arriving in Newport, take antsy passengers ready to stretch their legs to the Cliff Walk, a 3.5-mile walking path with sweeping views of oceanfront, Gilded Age mansions and the sea beyond. Audio tours featuring information about the most important families of that age can be added to the experience.

Book a room at Hydrangea House Inn where a cozy porch just begs for morning chats over coffee. Or take a quick drive or bike to Fort Getty Park and Campground where you and the group can see if your friendship can handle sharing a tent.

Amherst, MA

Head west from Boston long enough and you’ll soon be engulfed in an emerald sea of pine, maple, and hemlock trees.

Amherst is famously the home of many well-known writers, both living and dead. Literature-lovers should make a stop at the Emily Dickinson Museum to see the birthplace and home of the famous American poet. To please a slightly younger crowd of bookworms, visit The Eric Carle Museum of Picture Book Art to see illustrations from children’s favorites such as The Very Hungry Caterpillar and Brown Bear, Brown Bear, What Do You See?

In the warmer months, set out for the Amherst Farmers Market to pick up a loaf of fresh sourdough from Berkshire Mountain Bakery or a pick me up from Stout Pigeon coffee. But if a chill fills the air and walking around a historical sight or museum doesn’t suit a more sedentary-minded group it’s easy to spend the afternoon at Amherst Cinema, followed by dinner at Lili’s, a local favorite for authentic Xi’An Chinese Cuisine. Specials include Biang Biang handmade noodles and dumplings. 

Choose to rest at the Inn on Bolton, a historical hotel originally built in 1926 and refurbished in 2011, where you’ll find a complimentary coffee and newspaper awaiting you each morning.

Rockport, MA

For a quick escape from city life, Rockport, Massachusetts is the perfect pick. Located on the easternmost tip of Cape Ann, Rockport is usually represented by Motif #1, an iconic red fishing shack at the end of a dock in Rockport Harbor.

Take a bike or kayak over to Thacher Island, the former home of mafia-hitman-turned-informant, Joe “The Animal” Barboza, which is also the only known place in the United States to spot twin lighthouses. If the island doesn’t satiate the need for a little adventure, on your group’s next stop, take a dip in Back Beach, a spot for beginner scuba divers to get their feet wet.

After a jam-packed day of land and sea, grab a sweet treat at The Ice Cream Shop, whose nostalgic storefront appears to be pulled right from a 1980s rom-com featuring a summer love in a small beach town. If the traditional ice cream on a cone doesn’t float your boat, try out the Summer Breeze, a blended drink with sherbet and lemonade, instead. Refreshing treat in hand, take a stroll through the rest of Bearskin Neck, a historical commercial dock area, and pick up some souvenirs at the Rockport Candle Company, Slant Rhyme Studio, Carol Lee’s Cottage or any number of coastal shops on the edge of the Altanic.

Mystic, CT

If you want to be far enough away from Boston to go from staycation to true vacation, head to the town of Mystic, Connecticut, which sits on the Mystic River, in the southwest corner of The Nutmeg State.

Grab a pick-me-up breakfast sandwich and coffee at Mystic Depot Roasters. We recommend the special bacon, egg and cheese called The Mystic. Then, take your refreshments to the Peace Nature Sanctuary, named for its significant historical “peace meetings” during social justice movements of the 1800s, and where visitors can find the vestigial structures of Camp Mystic, a girls summer camp which existed in the 20th century on this 30-acre land preserve alongside wild pink lady slippers. (The flower, not the shoe.) If you want to see more than just flora and fauna, The Mystic Aquarium offers close-ups with penguins and tiger sharks or go back in time to the 1870s at the Mystic Seaport Museum Adventure.

Sliding into a blue, diner-style booth at Mystic Pizza to share a large house-special pie is the perfect way to rest your weary legs after a day spent sight-seeing. In the evening, pop by Deviant Donuts for sweet treats shaped for some of the sights and sounds of Mystic.

And if a sugar coma takes hold, spend a night at the Taber Inn or take a trip further back in history to the House of 1883 Bed and Breakfast.

Albany, NY

Clocking in at about 2 hours and 40 minutes away from Boston, Albany is the oldest city in the state of New York, the home of the state capitol building, and known for a breakfast-sounding performance art center called The Egg, as well as a spring tulip festival celebrating its Dutch roots.

Take your crew to Albany’s Empire State Plaza to take a peek at the seemingly endless reflecting pool. Keep walking toward the southern end of the plaza to the New York State Museum and New York State Library. Originally built in 1914, the New York State Museum Carousel is perfectly suited to a large band of friends or family as the “working artifact” requires at least 10 riders.

Take a ride around town with Albany’s new bike sharing program called CDPHP. Pedal the affordable, green mode of transport to Bon Appetit, on Wolf Road, in for Middle Eastern and American fusion fare. Wash down your falafel plate with Albany’s own Nine Pin Cider at Nine Pin Cider Works. It’s easy to find by its distinctive green “Drink NY” siding. For dinner and a show, stop by the historical Palace Theatre, a 2,800-seat venue built in 1931.

Accommodations can be found at the quaint Century House, where breakfast is included.

Conway, NH

This two-and-a-half-hour drive allows you just a glimpse of the expansive White Mountains in Conway, New Hampshire. Before embarking on a sojourn, fuel up at Peach’s Restaurant—you can’t miss the vibrant paint on the facade in the same shade as the establishment’s name. Order the lemon crepes if you’re feeling sweet or, for a more savory option, the eggs Benedict crepes. Or head over to The Met Coffeehouse, a locally owned establishment that offers locally roasted coffee beans to boot.

One in town, take a step closer to the living history of Conway on the Conway Scenic Railroad. The Mountaineer train ride will take you and your party on a journey through the viridescent valleys of the Crawford Notch. For an extra fee, lunch will be provided on the journey. Just outside North Conway is Diana’s Baths, where 75 feet of cascading waters can be found just a quick, and fairly easy hike from the parking lot. For a more quiet body of water, the 24-acre Pequawket Pond Preserve sits right in Conway waiting for visitors to enjoy an afternoon of quiet reflection amongst the local wildlife.

With a more whimsical audience in mind, take a quick car ride outside of Conway to the fairy-themed to Story Land. Take younger folks up on the Great Balloon Chase or Swan Boats and end the afternoon with an amusement park classic: ice cream. 

Portland, ME

At just 2 hours away from Boston, Portland, Maine brings the best of both words: medium city bustle and waterfront serenity. 

A quick eight-mile drive from the main city will land visitors at Crescent Beach State Park, where paddleboards and sea kayaks are available for rent. For indoor activities, try Another Round, a bar and cafe with more than 150 board games available to play. For a crew with green thumbs, visit Terrarium and leave with a DIY souvenir of personally curated plant creation.

Cultural centers such as the Portland Museum of Art or the Children’s Museum & Theatre of Maine provide the group an opportunity to see the works of greats classics or modern takes from locals. And don’t forget to check out Portland’s unique Victorian architecture at the Victoria Mansion. Portland’s homes, which are often made up of complex, colorful shapes on their facades, are great material to take a peek at while exploring this waterfront city on foot.

You’ll find Belgian-style fare at Duckfat, including sandwiches, fries and milkshakes. Take your food with you on a quick walk over to Fort Allen Park to enjoy the view of the salty seas as well.

The Old Orchard Beach Inn offers a homey approach to accommodations in the city. Or, stay right on the beach at the Atlantis Motel.

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