Massachusetts day trips: 9 family-friendly spots for the summer

Sunset at Menemsha, Martha’s Vineyard. (Massachusetts Office Of Travel & Tourism)

When I first moved to Boston’s North Shore in Massachusetts as a cub reporter in the early 1980s, I had a lot to learn. Coming from New Hampshire, I knew about Boston and Cape Cod, but not much else. And I had plenty of time to explore, provided I didn’t stray far from my apartment.

My reporting colleagues and I were supposed to work a “40-hour week,” but we were expected to be “on call” 24/7 (with no added pay, I might add). That translated to staying close to home. Since I was new to the area, I focused on visiting nearby attractions, like the beaches of Plum Island Wildlife Refuge, a birding paradise that is situated on the bustling Atlantic Flyway for migratory waterfowl; the properties of the Trustees of Reservation; and the Bay Circuit Trail. An early convert to mountain biking in the 1980s, I learned to ride off-road while learning more and more about my new surroundings.

It was, literally, a “back to the future” moment for me, because that’s what I did as a kid, when our favorite mode of transportation was our bikes (the original “trail bikes”) and our legs. I’ve taken the same approach to my adopted home state. But I’m the first to claim I’m not an expert on all things Massachusetts. For that kind of intimate local knowledge, I enlisted the help of an old friend, travel writer Steve Jermanok.

In his latest book, “New England in a Nutshell,” Jermanok distills many of the stories he’s written over the past quarter-century to a quick-read, round-up format. The more than 50 categories and 300 entries include 10 Classic New England Hikes, 8 Summer Drives That Will Keep You Smiling, 6 Hidden Art Historical Gems, Top 12 Country Inns to Get Pampered, and 6 Favorite Lobster/Clam Shacks. 

Here are some of our favorites:

Bay Circuit Trail and Greenway

Appalachian Trail visionary Benton McKaye first broached the idea of intertwining open spaces and communities around Boston, via recreational opportunities, in the 1920s. The Trustees of Reservations formally proposed the parkway in 1937, but while the state legislature approved the concept, it was never funded. In the 1980s, interest in the trail surged. The Bay Circuit Alliance was formed in 1990, and trail work resumed in earnest. In 2012, the Appalachian Mountain Club and the Trustees of Reservations took the reins of the alliance.

Today, thanks to the sweat equity supplied by an army of conservation-minded volunteers, the Bay Circuit Trail and Greenway is a 230-mile multi-use tapestry linking myriad patches of green spaces and 37 communities north to Newburyport and Ipswich, west to Sudbury and Framingham, and south to Kingston and Duxbury, creating an urban recreational greenway that allows convenient contact with nature for outdoor enthusiasts and neophytes alike. It includes dozens of entry points on private, quasi-public and public lands, including local, state and federal properties, both small and large — such as Harold Parker State Forest in Andover, Callahan State Park in Marlboro and Framingham, and Burrage Pond Wildlife Management Area in Hanson and Halifax, home to one of the world’s largest cranberry bogs.

Trustees of Reservations

Outdoor lovers in the commonwealth owe a debt of gratitude to the trustees, which is comprised of more than 100,000 members and manage more than 100 properties — accounting for more than 25,000 acres — throughout the state, from Agassiz Rock in Manchester-by-the-Sea and Boston Community Gardens to Swift River Reservation in Petersham and Notchview in Windsor. The deCordova Sculpture Park and Museum in Lincoln, Fruitlands Museum in Harvard, Castle Hill on Crane Estate in Ipswich, and the gardens of Stevens-Coolidge Place in North Andover are special sites.

South Shore

Within a short drive of Boston, Quincy and Hingham provide a welcome respite from the asphalt jungle. Some of the best rock climbing in Massachusetts is found at the Quincy Quarries Reservation (these quarries are also known for providing the stone used for the famed Bunker Hill Monument). The Adams National Historic Park and Boston Harbor Islands National and State Park are well worth your time. Nearby, the 6,000-acre Blue Hills Reservation has some of the best hiking and mountain biking trails in eastern Massachusetts.

With tree-lined carriage paths and sweeping views of the Boston skyline, only 15 miles away, World’s End reservation in Hingham (a Trustees of Reservation parcel) will make you feel like you’re worlds away from the city. The 251-acre coastal landscape includes rocky shores, broad hillsides and open fields bracketed by pockets of woodlands, making it an ideal escape for walking, picnicking, jogging, horseback riding or simply enjoying nature and the outdoors. 

There are a number of quaint shops in Hingham, as well as Bathing Beach, a great spot to watch the boating set sail by. For lunch, stop by the Bloomy Rind, which offers a great selection of gourmet cheeses and sandwiches.

Cape Cod

True story: Back in my “wild single days,” shortly after graduating from college, my buddies and I had a good friend who lived in Falmouth on Cape Cod. So on Friday nights, we’d go dancing in Boston, and when the clubs shut down well after midnight, we’d set off for Cape Cod. It is the only way to avoid mid-summer weekend traffic jams. Still, Cape Cod is worth the inconvenience. From kitschy to classy, the Cape offers myriad attractions.

“Cape Cod is blessed with a fantastic web of bike trails. Drive to the Orleans Cycle Shop and park, heading towards Eastham on the Cape Cod Rail Trail,” said Jermanok. “Then veer off the CCRT to the Salt Pond Visitors Center, where there’s another fantastic bike trail that dips and curves through forest to Nauset Light Beach. Watch the seals poke their heads out of the water like periscopes. Then head back to the CCRT and Orleans, stopping first at Arnold’s for the requisite lobster roll and onion rings.”

The Beachcomber in Wellfleet, the Cape Cod National Seashore, the artist colonies of Provincetown, the Heritage Museum and Gardens in Sandwich, and the John F. Kennedy Hyannis Museum also should be on your to-visit list.

Martha’s Vineyard 

Like Cape Cod, I prefer Martha’s Vineyard during the spring and fall, when the island takes on a more relaxed pace. But there’s no denying the electric vibe on Martha’s Vineyard during summer, when a surge of vacationers brings a seasonal energy.

“This is another fantastic biking locale, especially when the crowds leave in September,” said Jermanok. “Take the one-hour ferry from New Bedford, where ample parking is available, and soon you’re biking from Oak Bluffs on to Edgartown and the island of Chappaquiddick.”

Don’t overlook the raw and beautiful fishing village of Menemsha, on the western edge of Martha’s Vineyard, and the stunning clay cliffs of Gay Head.

New Bedford 

Nestled in the southeast corner of the commonwealth, New Bedford is home to the largest Portuguese community in North America, which is evident in a number of outstanding dining options. My college sweetheart was a native of Lakeville, just outside New Bedford, and during our sojourns to her home we’d go out to eat, and I learned to love delicacies such as sea scallops and quahogs. 

The New Bedford Whaling Museum is the best place to start so you can see how whaling played a major role along the New England seaboard in the 19th century. Then wander down the cobblestone streets to the same Seamen’s Bethel (home of the New Bedford Port Society) that Herman Melville wrote about in Moby Dick. 

“You can still see memorial tablets dedicated to the whalers who lost their lives,” said Jermanok. “Afterwards, end your day with a meal at a Portuguese restaurant like Antonio’s.”

Looking to get back to nature? The  516-acre Copicut Woods in nearby Fall River is both a prime destination and the southern gateway to the 13,600-acre Southeastern Massachusetts Bioreserve. 

North Shore

Salem, the “Witch City,” forever will be associated with one of the most harrowing and deplorable chapters in American history, the Salem Witch Trials that claimed 20 innocent victims (those kangaroo court sessions actually took place in neighboring Danvers, which was part of Salem at the time). For that reason alone, you want to avoid Salem during the last half of October. Trust me on this.

But this city is awash in history, from the House of Seven Gables made famous by Nathaniel Hawthorne, and a rich sailing tradition that made Salem a major player in a fledgling nation’s economy, highlighted by the Salem Maritime National Historic Site.

“Salem-Peabody Essex is a gem of a museum, with an eclectic mix of wares from 19th-century scrimshaw to the Yin Yu Tang House, brought over in its entirety from China,” said Jermanok. “Right behind the Peabody Essex is one of my favorite cemeteries, with headstones dating from the 1700s.” 

Salem also is home to a growing cuisine scene, with a number of superb restaurants reflecting numerous ethnicities crowding a bustling downtown. And for true students of the witch trials, visit the Rebecca Nurse Homestead in Danvers, commemorating one the victims of this travesty, and featuring a reproduction of the 1672 Salem Village Meeting House.

Cape Ann

East of the Annisquam River, Cape Ann is made up of Rockport, a town best known for high-quality granite, the arts and a stubborn adherence to Prohibition, and the nation’s oldest seaport, Gloucester (which is actually split by the river). Combined, they offer an abundance of natural and manmade riches, enough to nurture mind, body and soul. But ignoring the outlying towns of Essex, Manchester-by-the-Sea and Ipswich that make up the commonwealth’s “other” cape would be a shame.

This intriguing patchwork of marshland, farms and seaside villages, steeped in maritime history and brimming with character, make for a energizing escape that adventure seekers, nature lovers, art enthusiasts and travel buffs crave. Plus, it doesn’t draw the same suffocating throngs as Cape Cod to the south. That doesn’t mean that Cape Ann can’t feel a little cramped between Memorial Day and Labor Day. But on the whole, you’ll find yourself with a little more elbow room to explore.

Niles Beach on Gloucester’s Eastern Point is a draw for windsurfers, kiteboarders and paddleboarders, as is the stretch of sand at Pavilion Beach in Ipswich between Great Neck and Little Neck. Surfers congregate at Rockport’s Long Beach, while scuba divers favor Back Beach in Rockport or Manchester’s little-known White Beach. Popular spots for sunbathing and beachcombing include Gloucester’s Good Harbor Beach and Wingaersheek Beach, Ipswich’s Crane Beach, and Singing Beach in Manchester. Essex River Basin Adventures in Essex provides all kinds of rental gear.

“The combination of beaches and clam shacks on the North Shore of Massachusetts is unbeatable,” said Jermanok. “When the kids were younger, we loved gently sloping Wingaersheek Beach in Gloucester.

“These days, we usually head to Crane Beach in Ipswich, stopping at Russell Orchards to pick strawberries (or apples),” he said. “Afterwards, all roads lead to Woodman’s, which supposedly invented the fried clam over a century ago.”

North Adams 

For a longer day trip, take the classic Mohawk Trail through the countryside to the Berkshire Mountains and stop in at the largest contemporary art museum in the country, the Massachusetts Museum of Contemporary Art, better known simply as Mass MoCA. “It took 12 years to transform the buildings of the former Sprague Electric Company into an art extravaganza that now spans 26 buildings across 16 acres,” said Jermanok. “The latest addition in 2017 includes works by light artist James Turrell, whose pieces bathe the rooms in hypnotic colored lights.”

The North Adams Museum of History and Science is another attractive option in town. If you feel like heading outdoors, you can find great trails on the slopes of nearby Mount Greylock, the state’s highest peak at 3,491 feet. There’s also the Natural Bridge State Park offering great trails and picturesque views. Cool off after your adventures with some liquid refreshment at Bright Ideas Brewing.