The 10 best Massachusetts day trips in state and beyond, perfect for hiking, shopping, scenic views


As the temperatures rise and school lets out for the summer, it’s a good time to find new places to explore.

Whether those day trips take you to the Berkshires, out east to the shore or to another New England state, each one of these has its own charm perfect for anyone looking to get away.

Will your summer take you to any of these locations?

Purgatory Chasm State Reservation

Town: Sutton, MA

Purgatory Chasm is a unique natural state reservation landmark offering endless ways to explore the outdoors. “Follow trails to rock formations such as The Corn Crib, The Coffin and Lovers’ Leap. After exploration, settle down for an afternoon picnic,” wrote about the park. There is a parking fee to state residents for $5 and $20 for out of state. Inside the park, patrons have access to grilling, restrooms, a playground, picnic areas and the visitors center. The reservation is open from sunrise to sunset.

Purgatory Chasm

Purgatory Chasm.

Mount Holyoke Range State Park

Town: Amherst, MA

Fans of hiking can enjoy the scenic view from way up in the mountains. “The 3,000-acre Mount Holyoke Range State Park features a 7-mile mountain ridge line. The park also includes streams, wetlands, woods, and thickets. Visitors can explore more than 30 miles of blazed trails,” wrote. Parking is free and the park is open Sunday-Saturday from 9 a.m. to 4 p.m.

Mount Holyoke Range State Park

Mount Holyoke Range State Park (Massachusetts Office of Travel and Tourism)

Mystic, CT

The town of Mystic in Connecticut has so much to offer if you don’t mind taking a drive over state lines. The town includes many options for attractions like the aquarium, dining, shopping, recreation and lodging. With a purchase of a Mystic Pass, buyers will get one admission to Mystic Aquarium and one admission to Mystic Seaport Museum. You can browse Mystic’s website here.

Mystic, Connecticut

In 1933, a man was bitten by a shark in Mystic, Connecticut.

Mount Greylock State Reservation

Town: Lanesborough, MA

For the hikers who really want a thrill, Mt. Greylock is the highest point in Massachusetts at 3,491 feet, according to The park is also one of the best camping spots for hikers. The campsite features 27 camping sites along the base of the mountain packed with picnic tables, fire rings, hiker shelters, bear-proof food storage lockers and solar-powered composting toilets.

Mt Greylock mountain

An aerial photo of Veterans Memorial Tower on top of Mount Greylock.

Woods Hole

Town: Falmouth, MA

Located on Cape Cod, there is so much to do here that can fill up the day. Take a trip on the Steamship Authority, visit the Nobska Point Lighthouse or the Woods Hole Science Aquarium. The town also has an array of beaches and restaurants. Look for a
full itinerary list of what to do in Woods Hole here.

Woods Hole, Massachusetts

A view of Woods Hole, Massachusetts. The village in Falmouth was named one of “40 American towns you haven’t heard of but should visit ASAP” by Town & Country magazine. (BenFrantzDale/Wikimedia Commons)

Rockport, MA

Just north of Boston, this quaint town is a great option for those looking to spend the day. The town comes complete with shops, a small beach, a jetty and more. “Visit Rockport for our miles of lovely beaches, boulder-strewn paths through woods and glades, and that uncommonly magical light that has inspired painters since Winslow Homer. In an hour’s pleasant drive north of Boston, you can enjoy a romantic getaway, exquisite dining and a unique shopping experience year round,” Rockport’s website states. For a full look at the Rockport map, click here.

Rockport, Massachusetts

Rockport, Massachusetts. (Lisa Poole/AP)

Lee Premium Outlets

Town: Lee, MA

Not everyone wants to get active on a day trip. If hiking isn’t the right fit, leisurely strolling through the Lee Premium Outlets is a great way to spend a day. For shopping lovers, the outlets offer a vast selection of stores and places to eat. The outlets are open Monday to Thursday from 10 a.m. to 6 p.m., Friday to Saturday from 10 a.m. to 8 p.m. and Sunday’s from 12 p.m. to 6 p.m.

Lee Premium Outlets

Lee Premium Outlets. (Premium Outlets)

Castle Hill on the Crane Estate

Town: Ipswich, MA

Castle Hill is a 56,881 square foot Tudor Revival mansion in Ipswich, Mass., built from 1926 to 1928. “Castle Hill is a hiker’s paradise with hiking circuits that wind through manicured gardens, lawns, and paths,” according to Trustees. Tours of the house are available with both guided and self-guided options. Visitors can even play croquet on the lawn, or just hang out inside the guest houses. The house even looks out to an ocean view of Crane Beach.

Crane Beach in Ipswich, Massachusetts

Crane Beach in Ipswich, Massachusetts. (Chitose Suzuki/AP)

Cape Ann whale watching

Town: Gloucester, MA

Cape Ann Whale Watch in Gloucester “provides guaranteed whale sightings for every whale watching tour out to Stellwagen Bank, a national marine preserve about 12 miles off the coast of Gloucester,” according to the See The Whales website. Booking a whale watching session is available here. Day trippers can also check out Good Harbor Beach in Gloucester if whale watching isn’t enough.

Good Harbor Beach in Gloucester, Massachusetts

Good Harbor Beach in Gloucester, Massachusetts. (AP Photo/Lisa Poole)AP

Salem, MA

If Halloween is too spooky, visiting the town of Salem is a lot more tame in the summer. Known for the 1692 witch trials, this town has a haunting history. Guests can tour the Witch House, the home of Judge Jonathan Corwin and the only structure in Salem with direct ties to the witch trials, according to the house’s website. “It is also full of colonial architecture, world-class museums, shopping, and restaurants,” Adventures in New England wrote.

Names of Victims of the Salem Witch Trials

Massachusetts lawmakers on Thursday, May 26, 2022, formally exonerated Elizabeth Johnson Jr., clearing her name 329 years after she was convicted of witchcraft in 1693 at the height of the Salem Witch Trials. (AP Photo/Stephan Savoia, File)AP

Have a favorite day trip that didn’t make the list? Email [email protected]

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