Shannon O'Brien Travel Itineraries

The best destinations

Photo of Massachusetts
Photo of Massachusetts

The Best of Massachusetts

#45 best destination in the world

Map view

Flagstaff Hill, Boston Common

Photo of Boston Common

Walk difficulty: Easy

Best time to visit: June-Oct

Cost: $

  • Public park in downtown Boston, and the oldest city park in the United States
  • Firework displays over Boston Common began as early as July 3, 1745 in celebration of the fall of Louisburg, and the first anniversary of the signing of the Declaration of Independence on July 4, 1777

Freedom Trail

Photo of Freedom Trail

Walk difficulty: Easy

Best time to visit: June-Oct

Cost: $

  • 2.5-mile-long (4.0 km) path through Boston that passes by 17 locations significant to the history of the United States
  • Stops along the trail include simple explanatory ground markers, graveyards, notable churches and buildings, and a historic naval frigate

Museum of Fine Arts Boston

Photo of Museum of Fine Arts Boston

Best time to visit: June-Oct

Cost: $

  • Art museum in Boston, and the 20th-largest art museum in the world, measured by public gallery area
  • It contains 8,161 paintings and more than 450,000 works of art, making it one of the most comprehensive collections in the Americas

Coast Guard Beach, Eastham

Photo of Eastham

Best time to visit: May-June, Sept-Oct

Cost: $

  • Beach that is part of the Cape Cod National Seashore in Eastham, and is popular among locals and tourists for surfing and boogie boarding
  • It is one of five Cape Cod National Seashore beaches that are on the ocean side of the Cape, generally providing a better surf than beaches on the bay side

Faneuil Hall Marketplace

Photo of Faneuil Hall Marketplace

Best time to visit: June-Oct

Cost: $

  • Indoor/outdoor marketplace and food eatery, whose success in the late 1970s led to the emergence of similar marketplaces in other U.S. cities
  • Opened in 1742, it was the site of several speeches by Samuel Adams, James Otis, and others encouraging independence from Great Britain

Nantucket Whaling Museum

Photo of Nantucket

Best time to visit: March-April, Sept-Oct

Cost: $

  • Museum located in Nantucket that interprets The Hadwen & Barney Oil and Candle Factory as an industrial site where the complicated process of refining oil and making spermaceti candles is explained, along with the other Nantucket industries that arose from the whaling era
  • Eleven galleries and exhibit spaces featuring artifacts and art pertaining to Nantucket life, art, and ideas are on display
  • The museum displays a 46 foot (14 meter) long sperm whale skeleton is suspended from the ceiling

Heritage Museums and Gardens, Cape Cod

Photo of Cape Cod

Best time to visit: May-June, Sept-Oct

Cost: $

  • Public garden, with a nationally significant collection of rhododendrons hybridized over 1,000 varieties of daylilies and an extensive hosta collection, complemented by three gallery buildings containing a world-class collection of American automobiles, American folk art and a working 1919 carousel, as well as rare carousel figures

Great Island Trail, Cape Cod National Seashore

Photo of Cape Cod National Seashore

Walk difficulty: Moderate

Best time to visit: May-June, Sept-Oct

Cost: $

  • National Seashore that includes ponds, woods and beachfront of the Atlantic coastal pine barrens ecoregion, along the eastern shore of Cape Cod

Bunker Hill Monument

Photo of Bunker Hill Monument

Walk difficulty: Easy

Best time to visit: June-Oct

Cost: $

  • Monument erected at the site of the Battle of Bunker Hill in Boston, which was among the first major battles between the Red Coats and Patriots in the American Revolutionary War
  • The Americans, having caught word of a British plan to fortify the Charlestown peninsula, decided to get to the peninsula first, fortify it, and present sufficient threat to cause the British to leave Boston
  • A force of 1,500 colonists held off two British Army attacks, but the third attack, by British Royal Marines, forced the rebels to retreat
  • Though it was a tactical victory for the British, the battle had demonstrated that inexperienced militia were able to stand up to regular army troops in battle

Good Harbor Beach

Photo of Good Harbor Beach

Walk difficulty: Easy

Best time to visit: Sept-Nov

Cost: $

  • Small beach with prime swimming conditions, surrounded by dunes and marshes

Aquinnah Cliffs Overlook, Martha's Vineyard

Photo of Martha's Vineyard

Best time to visit: March-April, Sept-Oct

Cost: $

  • Clifftop observation point with sweeping views of the Atlantic, and a lighthouse, which is a popular viewing location at sunset

Six Flags New England

Photo of Six Flags New England

Best time to visit: June-Aug

Cost: $

  • Amusement park located in Agawam, opening in the late 19th century, it is the oldest amusement park in the Six Flags chain
  • Superman The Ride is among the park's most notable rides, having appeared as a highly ranked roller coaster since the ride opened

Springfield Museums

Photo of Springfield

Best time to visit: June-Aug

Cost: $

  • Springfield Museums operates the Dr. Seuss Memorial and five museums on the Quadrangle
  • Several statues depicting Springfield native Theodor Geisel (Dr. Seuss) and many of his creations were sculpted and placed on the Quadrangle green, known as the Dr. Seuss National Memorial Sculpture Garden
  • The George Walter Vincent Smith Art Museum is the oldest museum on the Quadrangle, and displays objects from ancient Egypt, China, Greece, and Rome

Tower Hill Botanic Garden, Boylston

Photo of Boylston

Walk difficulty: Easy

Best time to visit: June-Oct

Cost: $

  • New England Botanic Garden at Tower Hill is a 171-acre botanic garden and arboretum located in Boylston
  • The Garden features 18 distinct gardens, preserved woodlands, and miles of walking trails
  • It was founded in 1986 on the former Tower Hill Farm by the Worcester County Horticultural Society, which is the third oldest horticultural society in the U.S.

Isabella Stewart Gardner Museum

Photo of Isabella Stewart Gardner Museum

Best time to visit: June-Oct

Cost: $

  • Art museum in Boston, which houses significant examples of European, Asian, and American art
  • Its collection includes paintings, sculpture, tapestries, and decorative arts
  • The museum was built in 1898–1901 by Isabella Stewart Gardner, an American art collector, philanthropist, and patron of the arts in the style of a 15th-century Venetian palace

Fenway Park

Photo of Fenway Park

Best time to visit: June-Oct

Cost: $

  • Baseball stadium located in Boston, that since 1912, has been the ballpark of the Boston Red Sox
  • It is the oldest active ballpark in Major League Baseball

Boston Public Garden

Photo of Boston Public Garden

Walk difficulty: Easy

Best time to visit: June-Oct

Cost: $

  • Large park in the heart of Boston that was the first public botanical garden in America
  • The Public Garden contains a pond and a large series of formal plantings that are maintained by the city and others and vary from season to season
  • The garden is designed in the style of an English landscape garden

Halibut Point State Park, Rockport

Photo of Rockport

Walk difficulty: Easy

Best time to visit: Sept-Nov

Cost: $

  • State park that conserves oceanside land located on Cape Ann in the town of Rockport
  • The park offers trails and tidepools, ledges for picnicking, and expansive ocean views