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When it comes down to planning your day-to-day list of things to do, ShermansTravel experts have you covered. To make sure you get the most out of your vacation, we recommend the can't-miss museums and attractions, as well as the off-the-path activities and unique local experiences that will make your trip truly memorable.

Things to do in Massachusetts

Institute of Contemporary Art

Make time to explore ICA’s collection of modern masterpieces, which includes works by Paul Chan, Nan Goldin, and Boris Mikhailov. At the very least, stroll down to the seaport to see the dramatic Diller Scofidio + Renfro-designed building.

100 Northern Ave., MA, 617-478-3100
Tags: family | art | things to do | culture | architecture | museum

Mass Moca

For a rainy day diversion visit the massive Mass MoCA, a 13-acre contemporary art mecca that includes 27 former factory buildings which play host to a crossbreed of visual and performing arts. The museum has made itself a destination for novice art lovers and serious critics alike.

87 Marshall St., MA, 413-662-2111,
Tags: arts and culture | things to do | museum | performing arts

Mount Greylock

Head to the Berkshires to hike the highest peak in Massachusetts – 3,491-foot Mount Greylock. Those who make it to the summit enjoy panoramic views of the surrounding countryside. (Due to ongoing renovations, roads are closed to public access until 2009.)

Western Mass, MA, 413-499-4262,
Tags: hiking | views | things to do | outdoors


Known as a mecca for alternative lifestyles, Northampton is a small town with big-city appeal. Eclectic cafes, vintage clothing boutiques, kitschy shops, art galleries, and diverse restaurants line Main Street. Poetry readings and concerts are commonplace.

Western Mass, MA,
Tags: family | art | things to do | culture | history

Old Sturbridge Village

Experience 19th-century life at the Northeast’s largest outdoor history museum. Forty restored, original buildings, including homes, a country store, and a meetinghouse, contribute to the 200-acre village, which is brought to life by costumed actors.

Blackstone Valley, 1 Old Sturbridge Village Rd., MA, 508-347-3362,
Tags: family | things to do | culture | architecture | history

The Freedom Trail

Get acquainted with Boston and American Revolutionary history at the same time on the 2.5-mile-long Freedom Trail. The red-brick lined path winds past 16 historical sites, including the Paul Revere House and the USS Constitution warship.

Starts at 148 Tremont St., MA, 617-357-8300,
Tags: family | things to do | outdoors | culture | architecture | history

The Mohawk Trail

Originally a Native American trail, this scenic automobile route is the best place to catch the fiery spectacle of the fall leaves. Stop en route at Whitcomb Summit – at 2,272 feet, it affords awesome views of the surrounding forest.

Western Mass, State Route 2 from Millers Falls to Williamstown, MA,
Tags: family | views | things to do | outdoors

Wellfleet OysterFest

Wellfleet Bay Wildlife Sanctuary turns a brilliant vermilion, creating the perfect backdrop for slurping bivalves.

Main St., MA,
Tags: views | things to do | wildlife

Whale watching

Dedicate an afternoon to seeking out these majestic, marine animals off the coast of Gloucester and Cape Ann. Seven Seas runs guided boat tours that take you to their feeding hotspots and provide educational narrative along the way.

7 Seas-Whale Watch, South Shore; 7 Seas Wharf on Route 127, MA, 888-283-1776,
Tags: smart splurge | things to do | outdoors | wildlife

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