Take a Moment for a Family Road Trip in Massachusetts

The Bay State is full of travel memories waiting to be shared by generations.

By Yankee Staff

Jun 11 2023


Hancock Shaker Village, Pittsfield

Photo Credit : Massachusetts Office of Travel and Tourism

Sponsored by the Massachusetts Office of Travel and Tourism

The classic New England road trip has its roots right here in the Bay State. In 1914, the Mohawk Trail, a 69-mile stretch of road through northwestern Massachusetts, became the region’s first scenic byway — not to mention one of the earliest auto touring routes in the country. With that designation, it introduced a new wave of visitors to some of the most scenic beauty in New England.

Hancock Shaker Village, Pittsfield
Photo Credit : Massachusetts Office of Travel and Tourism

But a memorable road trip is about so much more than just the scenery. And in Massachusetts, there’s no shortage of fun to explore along the way, especially for families. There are award-winning zoos and museums, sandy beaches and stunning hikes, adventure-themed mini golf courses, and historical sites where all ages can learn something new. So pack the cooler, grab the kids, and let’s go!

1. Merrimack Valley/Greater Boston

Lowell to Boston; approximately 70 miles

Kimball Farm, Westford
Photo Credit : Massachusetts Office of Travel and Tourism

Farmland, sweet treats, and spectacular history define this itinerary. Begin your travels in Lowell, where the country’s industrial beginnings are celebrated at Lowell National Historical Park. Tour the refurbished mills that helped build the nation, then hop a canal tour for a unique look at the city and the remarkable water system that once powered it. Moving on to Westford, you’ll find lunch and something to sweeten your day at Kimball Farm, known for family fun (mini golf, bumper boats), fried seafood, and 50-plus flavors of homemade ice cream. In neighboring Harvard, The Trustees’ Fruitlands Museum is a 210-acre showcase of art exhibitions, walking trails, and stunning views. Keep your step count climbing at the deCordova Sculpture Park and Museum in Lincoln, the largest sculpture park in New England, whose contemporary, large-scale installations scattered across 30 acres will appeal to art fans of any age. Just 10 minutes away, in Concord and Lexington, the Minute Man National Historical Park commemorates the opening battles of the American Revolution: Hike the famous Battle Road Trail, grab a selfie on the North Bridge, and help your youngster earn a Junior Ranger badge. Finally, end your road trip in Boston, where a week of exploring family activities would still only scratch the surface.

DeCordova Museum and Sculpture Park, Lincoln (“Two Big Black Hearts” by Jim Dine)
Photo Credit : Kindra Clineff

The capital of Massachusetts and the largest city in New England, Boston is a cosmopolitan destination with 23 vibrant neighborhoods to explore, diverse multicultural cuisine, and a history of innovation that spans everything from the invention of the telephone to advances in gene editing. Among the don’t-miss attractions are the Seaport’s Boston Tea Party Ships & Museum; the Public Garden’s venerable Swan Boats; Fenway Park, the oldest ballpark in the nation; and the Charles River Esplanade, home to the annual Boston Pops Fireworks Spectacular. But for getting your bearings, you can’t beat a trip up to the brand-new View Boston (opening June 15), a 360-degree observation deck in the Back Bay that offers breathtaking views of a city where rich history is infused with an exciting, thoroughly modern appeal.

Fourth of July on the Charles River Esplanade, Boston
Photo Credit : Massachusetts Office of Travel and Tourism

More suggested stops along the way: Lowell–Concord River Rafting with Zoar Outdoor; Westford–The Butterfly Place, Nashoba Valley Ski Area; Harvard–Carlson Orchards; Acton–Discovery Museum; Concord–Verrill Farm; Lexington–Liberty Ride Trolley Tour; Boston–New England Aquarium, Museum of Science, Puttshack, Boston Harbor Cruises, Boston Duck Tours

2. North Shore

Salisbury to Salem; approximately 50 miles

Crane Beach on the Crane Estate, Ipswich
Photo Credit : Holly Perry

It wouldn’t be a summer road trip without a little beach time, and a favorite stop in Massachusetts is Salisbury Beach, which runs nearly four miles long (make sure your visit includes a spin on the recently added Salisbury Beach Carousel). When you’re ready for some indoor diversion, head over to the Tannery Marketplace in Newburyport, a prime North Shore shopping destination with 50 different retailers as well as a large farmer’s market. Moving down the coast to Ipswich, you can marvel at Castle Hill on the Crane Estate, whose 365 on-the-water acres are managed by The Trustees and anchored by a 59-room Stuart-style mansion; plus, another fine stretch of sand, Crane Beach, can be found here. In Essex, it’s all about the seafood — most notably at Woodman’s of Essex, birthplace of the fried clam — while those who want to try their sea legs can catch a whale watching tour from nearby Gloucester. Something witchy is always brewing in Salem, and at the Salem Witch Museum you can bone up on the history and legacy of the city’s infamous 18th-century trials. Just a few blocks away, the Peabody Essex Museum is not only home to the biggest collection of materials related to the witch trials, but also one of the largest art museums in North America. Its treasures are drawn from Massachusetts and far beyond, including a completely rebuilt Chinese house that’s more than 200 years old.

Hammond Castle Museum, Gloucester
Photo Credit : Colleen Blair

More suggested stops along the way: Amesbury–Amesbury Carriage Museum, Cider Hill Farm; Newbury–Spencer-Peirce-Little Farm; Gloucester–Hammond Castle Museum, Maritime Gloucester; Manchester-by-the-Sea, Singing Beach; Beverly, North Shore Music Theater; Salem–Real Pirates Salem, House of the Seven Gables, Mahi Cruises

3. South of Boston

Fall River to Plymouth; approximately 55 miles

Battleship Cove, Fall River
Photo Credit : Sergio Dabdoub

The big guns come out for this road trip — namely, Battleship Cove in Fall River, a maritime museum and war memorial where families can explore the world’s largest collection of World War II naval vessels. The sights are just as oversized in New Bedford, where the fascinating New Bedford Whaling Museum tells the rich story of this bygone New England industry, complete with several real whale skeletons and the largest model ship you’ll find anywhere. Visiting New Bedford in August? Look for the four-day Feast of the Blessed Sacrament, the world’s top Portuguese cultural festival. In East Wareham, kids will scream with delight at Water Wizz, southern New England’s biggest outdoor water park, whose famous Pirate’s Plunge has recently been revamped. In Carver and Plymouth, you can take a hike — and do so much more — at the 14,000-acre Myles Standish State Forest, which has miles of trails for hiking, biking, and horseback riding, plus a great swimming beach. (If you’re road-tripping through Carver in autumn, don’t miss King Richard’s Faire, New England’s biggest Renaissance festival, as well as tours of local cranberry bogs at harvest time.) Then swing over to the coast for a bit of time-travel at Plimoth Patuxet Museums, which brings to life the stories of the Pilgrims and the Indigenous people who came before them.  

The Bay State is full of travel memories waiting to be shared by generations.
Island Creek Oysters, Duxbury
Photo Credit : Colleen Blair

More suggested stops along the way: Westport–Horseneck Beach State Reservation; New Bedford–Buttonwood Park Zoo; Wareham–Great Neck Wildlife Sanctuary; Plymouth–Captain John Boats and Pilgrim Belle Cruises, Priscilla Beach Theatre;Duxbury, Island Creek Oysters

4. The Cape & Islands

Sandwich to Hyannis; approximately 60 miles

Pirate’s Cove, South Yarmouth
Photo Credit : Mark Fleming

This ramble through the Upper, Mid-, and Lower Cape begins in Sandwich, where you and your family can stop into the Sandwich Glass Museum to explore a kaleidoscope of rare, locally made glass and learn to make a treasure to take a home. Nearby, Heritage Museums & Gardens beckons with 100 acres of blooming wonders plus exhibits ranging from classic cars to folk art. Motor east to Dennis to visit the engaging Cape Cod Museum of Art and maybe catch a show at the Cape Playhouse, a summer-stock theater landmark since 1927. Outdoorsy activities await in Brewster’s Nickerson State Park, a prime spot for hiking, swimming, kayaking, and biking (in fact, its eight miles of bike trails connect to the popular Cape Cod Rail Trail, another regional highlight). Take a deep dive into the research and conservation efforts of the Atlantic White Shark Conservancy at the Shark Center Chatham (there’s a second outpost, Shark Center Provincetown, that just opened in 2022). Have some kids who love to play pirates? They can discover swashbuckling fun at Pirate’s Cove mini golf in South Yarmouth as well as visit West Yarmouth’s Whydah Pirate Museum. One of the Cape’s most beloved summer traditions is taking in a Cape Cod Baseball League game, as elite college players take the field in towns across the region. To learn about the league and its history, head to Hyannis’s new Cape Cod Baseball League Hall of Fame and Museum (opening July 22, 2023). And for those looking to break up their road trip with a little island time, Hyannis is also where you can catch a high-speed ferry to Martha’s Vineyard or Nantucket — where a whole new adventure begins.

Bass Hole (Gray’s) Beach, Yarmouth Port
Photo Credit : Betty Wiley

More suggested stops along the way: Brewster–Cape Cod Museum of Natural History; Yarmouth Port–Edward Gorey House, Bass Hole (Gray’s) Beach; Chatham–Chatham Fish Pier; Hyannis–Cape Cod Melody Tent, John F. Kennedy Hyannis Museum, Cape Cod Maritime Museum; Nantucket–Children’s Beach, Cisco Brewers, Nantucket Whaling Museum, Critter Cruise; Martha’s Vineyard–Polly Hill Arboretum, Flying Horses Carousel, Island Alpaca Company, Maria Mitchell Association

5. Central Massachusetts

Fitchburg to Brimfield; approximately 70 miles

New England Botanic Garden at Tower Hill, Boylston
Photo Credit : David Long

Orchards, antiques, and city delights give this road trip a feel all its own. Begin with Fitchburg and the Great Wolf Lodge, whose indoor water park and arcade offer a full day’s worth of fun. The action continues at Wachusett Mountain State Reservation in Princeton, where 3,000 acres are loaded with hiking and biking opportunities. There are cute animals to pet and outdoor mazes to explore at Davis Farmland in Sterling, while Boylston lures families with the New England Botanic Garden at Tower Hill, a 171-acre oasis that includes The Ramble, a kids’ attraction that’s half garden/half playground. For city lovers, Central Massachusetts’s urban flair shines brightest in Worcester: After exploring the city’s growing culinary scene, bring your curiosity to the EcoTarium, a nature and science museum with hands-on exhibits, nature trails, and a seasonal train ride. History, meanwhile, gets top billing at Old Sturbridge Village, a 200-acre living history museum that re-creates New England life in the early 1800s. Finally, grab a treasure from the past for your own home at the Brimfield Antiques Show in nearby Brimfield, where multi-day shows in May, July, and September pull in hundreds of exhibitors from around the Northeast.

EcoTarium, Worcester
Photo Credit : Massachusetts Office of Travel and Tourism

More suggested stops along the way: Fitchburg–Fitchburg Art Museum, Hollis Hills Farm; Sterling–Rota Spring Ice Cream; Clinton–Wachusett Reservoir Dam, Museum of Russian Icons; Worcester–Worcester Art Museum, Polar Park; Charlton–Tree House Brewing Company; Sturbridge–Wells State Park

6. Springfield & Pioneer Valley Through Hampshire/Franklin Counties of Western Massachusetts

Deerfield to Agawam; approximately 55 miles

Naismith Memorial Basketball Hall of Fame, Springfield
Photo Credit : Paul Schnaittacher

Kick off this ramble through Franklin, Hampshire, and Hampton counties with a visit to Yankee Candle Village in South Deerfield. At this, the state’s second most popular tourist attraction, your family can explore different scents, interactive exhibits, and possibly the world’s only candle-making museum. A short drive south brings you to Amherst and the chance to stroll the beautiful campus of historic Amherst College; don’t miss the the terrific, kid-friendly Beneski Museum of Natural History, filled with minerals and fossils from around the world. In nearby Northampton, you’ll find a thriving, walkable downtown with a bevy of international dining options — not to mention Herrell’s Ice Cream, which pioneered gourmet cookie and candy mix-ins in the 1970s. Hay rides, mini golf, and a petting zoo are all on tap at McCray’s Farm in South Hadley, while more than a century of basketball history takes the spotlight at the Naismith Memorial Basketball Hall of Fame in Springfield, the city where the sport was born. (If you’re visiting Springfield in the fall, don’t miss The Big E, the largest agricultural fair on the eastern seaboard.) For a grand finale, head over to Six Flags New England in Agawam, where the kids will delight in everything that goes up and down and all around at this expansive amusement park.

The Eric Carle Museum of Picture Book Art, Amherst
Photo Credit : Seth Kaye; image © The Eric Carle Museum of Picture Book Art

More suggested stops along the way: Deerfield–Historic Deerfield; South Deerfield–Mount Sugarloaf, Magic Wings Butterfly Conservatory & Gardens; Amherst–The Eric Carle Museum of Picture Book Art; Northampton–Norwottuck Rail Trail, Botanic Garden of Smith College; Springfield–Springfield Museums, The Zoo in Forest Park & Education Center, Springfield Armory

7. The Berkshires

Stockbridge to North Adams; approximately 40 miles

Tanglewood, Lenox
Photo Credit : Massachusetts Office of Travel and Tourism

The Berkshires region of Western Massachusetts comes into full focus on this road trip. The route begins in Stockbridge, which hometown artist Norman Rockwell helped put on the national map some three-quarters of a century ago. The power of his iconic illustrations endures to this day, and many of them can be explored at the Norman Rockwell Museum, home to the largest collection of Rockwell art in the world. In Lenox, summers are made for relaxing under the stars to the music of the Boston Symphony Orchestra at Tanglewood, while in Pittsfield you can step back in time at Hancock Shaker Village. Families can bring their hiking boots (and cameras) to Lanesborough, home to Mount Greylock State Reservation and the highest peak in Massachusetts. For the final leg, push northward to North Adams, which hosts one of the most ambitious museums in the country, MASS MoCA, and sits right on the scenic byway that began it all: the Mohawk Trail.

MASS MoCA, North Adams
Photo Credit : Lillie Marshall

More suggested stops along the way: Stockbridge–Berkshire Botanical Garden, Naumkeag; Lenox–The Mount: Edith Wharton’s Home, Berkshire Scenic Railway Museum; Lanesborough–Ramblewild Adventure Park, Ashuwillticook Rail Trail; Hancock–Jiminy Peak; North Adams–Wigwam Western Summit, Natural Bridge State Park