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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

“Campground” Cottages

Like something straight out of Alice in Wonderland, this picturesque 19th-century enclave, with its 300+ shockingly bright, diminutive cottages (formerly part of a Methodist campground), borders on surreal. At their center is the Tabernacle, unique for its octagonal cupola.

Oak Bluffs, MA, 508-693-0525,
Tags: family | architecture | historic | things to do | outdoors

Ahla Brookline Food Tour

If you're up for a nosh and want to delve into more Boston history, head off to nearby Brookline. Both the Walking Tour of Jewish Cuisine and the From Russia With Love! Tour will introduce you to local history that has nothing to do with the Freedom Trail. Meet the town's top purveyors of all things delicious (latkes, bagels, falafel and more) and, of course, eat. What could be better than that?

80 Park St. Suite 35, Massachusetts, 617-304-1570,
Tags: culinary | tour | walk | things to do | history

Boston Harbor Cruises

This company’s well-regarded boat tours range from sightseeing to whale watching. History buffs can take a break from the Freedom Trail during an easier-on-the-feet narrated harbor cruise, while photo fans can capture great images on a Lighthouse Cruise that sails past Thacher Island, home to the country’s last operating twin lighthouses. Crave adventure? Take a thrilling, high-speed spin on “Codzilla.”

One Long Wharf, MA, 877-733-9425,
Tags: cruise | culture | tour | whale watching | wildlife | things to do | history

Boston Public Library

It's part art museum, part history museum, part live-event venue, part restaurant, and, oh yeah, there are books here, too. The Boston Public Library also offers a fascinating (and free) architecture and art tour of its historic 1895 McKim Building (Sun. at 2 p.m., Mon. at 2:30 p.m., Tues. and Thurs. at 6 p.m., and Fri.–Sat. at 11 a.m.). It's no throwaway line to say that the BPL's central library has something for everyone.

700 Boylston St., Massachusetts, 617-536-5400,
Tags: family | architecture | culture | tour | things to do | history | art

Boston Symphony Orchestra

Making beautiful music since 1881, the Boston Symphony Orchestra offers a range of concerts that appeals to young listeners hearing their first live classical music as well as lifelong subscription holders. Amid the splendid setting of Symphony Hall, a visual and acoustic wonder in its own right, revolving works from Brahms to Wagner take musical flight. Free tours of the hall are available during the BSO season (Oct.–May).

301 Massachusetts Ave., Massachusetts, 617-266-1492,
Tags: culture | performing arts | things to do

Brant Point Lighthouse

For 250 years, this lighthouse – the second oldest in America – has kept ships from running ashore. At just 26 feet tall, you’ll wonder how this surprisingly short structure has done its job for so long. Parking isn’t close, but the walk is delightful.

Easton St., MA, 508-228-2500,
Tags: family | things to do | outdoors | history | great value

Cape Cod Baseball League

Take the whole family out to the ball game – it’s free! Scout out the future stars of Major League Baseball alongside real scouts at the country’s premier NCAA-sanctioned summer baseball league games. Ten different teams means there’s a game near you.

Tags: family | spectator sport | free | things to do

Cape Cod National Seashore

This 40-mile beach extending from Chatham to Provincetown is the Cape’s most popular summer attraction.

Outer Cape, MA,
Tags: beach | family | national park | things to do | editor pick

Cape Cod Rail Trail

Whether by foot, bicycle, or horseback, follow the 22-mile path of a now-defunct railroad to picturesque beaches, salt ponds, and marshes.

Mid Cape-Outer Cape, MA,
Tags: beach | family | hiking | things to do

Catch a Clam

All you need is a rake, a pail, and a permit. Head to bay beaches during low tide for the easiest clamming; permits are available in each town.

Tags: beach | family | wildlife | things to do

Charles Street

Mingle with Boston’s upper crust as you peruse the antique stores, specialty boutiques and upscale galleries that line this Beacon Hill street’s brick sidewalks. One don't-miss: Good (88 Charles St), a gift shop whose inventory of really good stuff ranges from whimsical toys to wow jewelry.

Charles St., MA,
Tags: gallery | things to do | expensive | shopping | antiques


The original Beacon Hill bar that served as the inspiration for the eponymous TV series, and whose exterior was shown in the opening credits, offers a happy hour (Mon.–Fri. 4–6 p.m.) with half-price appetizers. Pub-inspired food is served from 11 a.m. on and children are allowed on premises until 10 p.m. (there’s a kids’ food menu). Stay until closing and everyone is sure to know your name.

84 Beacon St., MA, 617-227-9605,
Tags: family | things to do | nightlife | bar | bar menu

Chicama Vineyard

Adding credibility to the island’s name, this winery – owned and operated by the Mathiesen family since 1971 – produces seven types of wines, including the more-than-worthy Chenin Blanc. After a free tour and tasting, pick up a bottle to bring home.

Stoney Hill Rd., MA, 508-693-0309,
Tags: tour | things to do | wine | editor pick

Coskata-Coatue Wildlife Refuge

Don your hiking boots – don’t forget your camera – as you set out over 16 miles of walking trails. This refuge (pronounced "co-skate-uh co-too") has 200 acres of dunes, a mature maritime oak forest, and salt marshes.

Just south of Wauwinet, Wauwinet Rd., MA, 508-228-5646,
Tags: family | hiking | things to do | outdoors | great value

Elephant Walk Cooking Classes

Get schooled by the beloved chefs/cooking instructors at The Elephant Walk restaurants. Classes – on everything from vegetarian comfort food to Cambodian curries – are a great way to bond with locals. After you all cook together, you eat together. And when you get home, your new kitchen skills will impress your friends. Sign up early since Saturday morning classes, held at The Elephant Walk restaurants in Cambridge and Boston, sell out quickly.

The Elephant Walk Restaurant, 2067 Massachusetts Ave., MA, 617-285-1056,
Tags: culinary | smart splurge | things to do | cooking class | educational

Faneuil Hall Marketplace

It's busy and crazy and sort of exhausting but it's also a Boston must. Knick-knacks and inexpensive souvenirs dominate the carts of vendors hawking everything from lobster lollipops to Boston-themed t-shirts. Plenty of typical mall stores are also on hand.

4 South Market Building, MA,
Tags: family | things to do | shopping | souvenirs | shopping mall

Felix Neck Wildlife Sanctuary

Dedicate an afternoon to trekking one of the six trails that thread this 250-acre sanctuary spanning woodlands, meadows, ponds, salt marshes, and barrier beaches. Keep an eye out for birds like ospreys, tree swallows, and wood ducks.

Felix Neck Dr. (Off Edgartown-Vineyard Haven Rd.), MA, 508-627-4850,
Tags: family | hiking | wildlife | things to do | outdoors

Fenway Park

This city has its fair share of churches, but none are considered as holy as the home of the Boston Red Sox. The team's fans – known collectively as Red Sox Nation – are one seriously loyal bunch. Learn all about their beloved circa-1912 stadium, including the infamous Green Monster, during daily tours. Want to see a game? Play begins in early April and runs through late September; for the best seats, buy tickets online long before heading to Beantown.

4 Yawkey Way, MA, 617-226-6666,
Tags: family | spectator sport | tour | things to do

Field Gallery

The Field Gallery, originally designed to showcase local talent, now includes the works of national artists, too. See local sculptor Tom Maley’s fanciful pieces outside, and rotating collections of paintings and photographs inside. Sunday afternoon receptions are a summer island tradition.

1050 State Rd., MA, 800-355-3090,
Tags: culture | things to do | outdoors | art

Freedom Trail

Hit 16 historical sites along the free, 2.5-mile red-brick Freedom Trail (which begins at the Visitor Information Center in The Boston Common) as it winds through several of the city’s must-see neighborhoods. In pleasant weather, it’s an enjoyable and heart-healthy stroll. But if it’s cold or you’re traveling with tots, there’s no need to tackle the whole thing in one day. Divide it in two and walk half one day, the other half the next, devoting some time to enjoying the surrounding neighborhoods. It's the best way to put history in context with the modern city.

148 Tremont St., MA,
Tags: walk | free | things to do | history | editor pick

Gay Head Lighthouse

Still in operation after 150 years, the scrupulously maintained Gay Head Lighthouse is a national landmark. Tour it at sunset for impressive views of Gay Head Cliffs and the Vineyard Sound.

9 Aquinnah Circle, MA, 508-645-9954
Tags: family | historic | things to do | views | editor pick


Tee times are plentiful on the Cape’s 29 public golf courses; Falmouth alone has six courses, more than any other town in New England.

Tags: golf | things to do | sports

Head of the Charles Regatta

Since 1965, the race has hosted an international lineup of handsome rowing crews, who annually congregate on the Charles River to compete in the world's largest regatta. Spectators line the banks while vendors and bands converge on the college town, creating a camaraderie that is pure Boston.

Charles River, MA,
Tags: spectator sport | things to do | festivals and events

Institute of Contemporary Art

Opened in late 2006 (as the city’s first new art museum in 100 years), the Institute of Contemporary Art's permanent home was a welcome addition to South Boston’s waterfront. Once inside, take the elevator to the light-soaked galleries on the top floor. You may not like everything up there, but it will certainly get you talking. Don't leave without a visit to the gift shop. Open Tues.–Wed. and Sat.–Sun. 10 a.m.–5 p.m.; Thurs.–Fri. 10 a.m.–9 p.m.

100 Northern Ave., MA, 617-478-3100,
Tags: architecture | museum | performing arts | things to do | art | editor pick

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 | architecture | culture | museum | things to do | art

Isabella Stewart Gardner Museum

View the collection of Isabella Stewart Gardner, who during her lifetime amassed over 2,500 eclectic words of art, including sculptures, paintings, furniture, and rare books. When you are finished exploring the masterworks, duck outside to relax in the exquisite garden courtyard. Make the most of your visit by reading up on Gardner before exploring her home – she was quite the interesting character. Open Tues.–Sun. 11 a.m.–5 p.m. (last admission at 4:20 p.m.).

280 The Fenway, MA, 617-566-1401,
Tags: culture | museum | things to do | art | gardens

Jethro Coffin House

Head to the island’s oldest residence to see how people lived back in 1686. In the warmer months, enjoy a stroll through the historic garden, which includes apple trees. Tours run mid-May through Mid-October.

Sunset Hill Rd., MA, 508-228-1895,
Tags: family | architecture | culture | things to do | outdoors | history

Martha’s Vineyard Museum

Curious about the evolution of Martha’s Vineyard? Over 30,000 artifacts ranging from paintings, sculptures, and costumes to decoys, hunting tools, and fishing boats, provide a comprehensive look at the island’s history.

59 School St., MA, 508-627-4441 x110,
Tags: family | things to do | history | editor pick

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: museum | performing arts | things to do | arts and culture

Miacomet Golf Club

This public golf course is open year round. Its views of coastline and Miacomet Pond might offer some solace if its challenging course gets the better of you.

Just west of Southside, 12 West Miacomet Rd., MA, 508-325-0333,
Tags: golf | things to do | outdoors | views | sports

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 | things to do | outdoors | views

Museum of Fine Arts, Boston

This vast museum contains traditional galleries featuring European, Asian, African, and American art, with special exhibitions – ranging from Italian masters to modernist photography – mounted on a regular basis. An expansion, completed in late 2010, tacked on a strikingly modern Art of the Americas Wing with exhibits highlighting centuries of work from North, Central and South America. Also notable is the grand, iconic-columned entrance on State Street overlooking The Fens. Open Mon.–Tues. and Sat.–Sun. 10 a.m.–4:45 p.m.; Wed. 10 a.m.–9:45 p.m.

465 Huntington Ave., MA, 617-267-9300,
Tags: family | museum | things to do | art

Nantucket Adventures

Spend three hours on the ocean with the “Seal Encounter” eco-tour. The boat’s design doesn’t disturb the seals so you can watch them without worrying about disrupting them. Tours run April 1st through October 31st.

Town Pier (Slip 77), MA, 508-228-6365,
Tags: family | wildlife | things to do | outdoors

Nantucket Chowder Festival

"Chowda" is a regional staple with more varieties than one can imagine. This one-day festival, which takes place on October 14, may not be the biggest, but it's our favorite.

Tags: culinary | things to do

Nantucket Island Community Sailing

The best way to see the island is from the water. Seasoned sailors can rent their own vessels, while novices can take advantage of private or group lessons to learn the craft. Open mid-June through Labor Day (weather permitting).

4 Winter St., MA, 508-228-6600,
Tags: family | smart splurge | things to do | outdoors

New England Aquarium

With jellyfish, seal, shark, and penguin exhibits, plus a four-story Giant Ocean Tank, The New England Aquarium is a great place to bring the kids – but you’ll have a fantastic time, too. There’s also an IMAX theater that rotates educational movies about marine and animal life on a 65-foot-tall screen. Open Sept.–June, Mon.–Fri. 9 a.m.–5 p.m. and Sat.–Sun. 9 a.m.–6 p.m.; July–Aug., Sun.–Thurs. 9 a.m.–6 p.m. and Sat.–Sun. 9 a.m.–7 p.m.

One Central Wharf, MA, 617-973-5200,
Tags: family | aquarium | wildlife | things to do | editor pick

Newbury Street

You can easily spend an entire afternoon on this eight-block-long shopper’s haven. No matter your brand of choice, from Marc Jacobs to Diesel to Burberry, they're all here. (But so are Gap and J. Crew, along with the Trident Booksellers and well-known alternative record shop, Newbury Comics.) Also home to more hair salons and spas than seem necessary, Newbury St. is the place to get pampered for a night on the town. Even if you don’t have money to burn, grab a coffee at a café and watch everybody else spend some.

Newbury St., MA,
Tags: gallery | things to do | expensive | shopping | jewelry | designer | clothing | accessories | editor pick | boutique


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 | culture | things to do | history | art

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 | architecture | culture | things to do | history

Rose Fitzgerald Kennedy Greenway

Where there was road, now there's a park. Actually, there’s a mile-long string of parks. During the Big Dig, after the city sank the elevated highway that cut through part of Boston, officials turned the ground left behind into a series of linked parks. Winding from symbol-rich Chinatown Park to water-jet-studded North End Parks, the Greenway is an ideal spot for a spring or fall stroll, a fun playground for kids, or just a refreshing place (or bunch of places) to sit and eat a sandwich.

Massachusetts, 617-292-0020,
Tags: family | things to do | outdoors | park | gardens

Swan Boats in the Boston Public Garden Lagoon

You have to ride them once (although kids will clamor for more, more, more). The Swan Boats have paddled around the lagoon of the Boston Public Garden since 1877. Afterward, stroll through the 24-acre gardens, which have been in bloom even longer, since 1837. Open daily, mid-Apr. to mid-Sept.

Bordered by Arlington, Boylston, Charles, and Beacon streets, Massachusetts, 617-522-1966,
Tags: family | things to do | outdoors | park | gardens

The Coop

If it's a Harvard or M.I.T. logoed item you're after, look no farther. But the real reason to check out The Coop is its books section. There, you’ll find every tome you didn't know you had to read but instantly want to own. It's a truly seductive place and you’ll feel smarter for simply having walked through the door.

1400 Massachusetts Ave., Massachusetts, 617-499-2000,
Tags: things to do | shopping | clothing | accessories | books

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 | architecture | culture | things to do | outdoors | 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 | things to do | outdoors | views

Wellfleet OysterFest

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

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

Whale watching

Summer is the prime time to spot whales; tours leave from Hyannis and Provincetown; book in advance to secure your spot.

Dolphin Fleet, MA, 800-826-9300,
Tags: family | whale watching | things to do | boating | editor pick

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: wildlife | smart splurge | things to do | outdoors

Whaling Museum

Get a reminder of Nantucket’s whaling past at this captivating museum. Its skeleton of a 46-foot long sperm whale is jaw-dropping, as are the downtown and harbor views from its roof.

15 Broad St., MA, 508-228-1894,
Tags: family | things to do | views | history

Yawkey Way Store

Just give in. Red Sox fever is so strong in Boston that, no matter which team you usually root for, you'll feel the need to own something Sox before you skedaddle on home. For a wall-to-wall Red Sox gear experience, simply step across the street from the stadium itself. Just don't go on a game day (unless you have tickets) since it can be so crowded it'll make you cry. (And even if you’re not a Sox fan you have to admit it's fun to say Yawkey.)

19 Yawkey Way, Massachusetts, 800-FENWAY-9,
Tags: family | things to do | shopping | souvenirs | clothing | novelty

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