39 Best Sights in Side Trips from Boston, Massachusetts

On a peninsula within Gloucester’s working harbor, the town's creative side thrives in this neighborhood, one of the oldest continuously working artists' colonies in the United States. Its alumni include Winslow Homer, Maurice Prendergast, Jane Peterson, and Cecilia Beaux. While some venues stay open year-round, expect many to be closed in winter; but no matter the season, it's a picturesque place.

Near Derby Wharf, this 9¼-acre site focuses on Salem's heritage as a major seaport with a thriving overseas trade. It includes the 1762 home of Elias Derby, America's first millionaire; the 1819 Custom House, made famous in Nathaniel Hawthorne's The Scarlet Letter; and a replica of the Friendship, a 171-foot, three-masted 1797 merchant vessel. There's also an active lighthouse dating from 1871, as well as the nation's last surviving 18th-century wharves. The 1770 Pedrick Store House was moved from nearby Marblehead and reassembled right on Derby Wharf; the two-story structure once played a vital role in the lucrative merchant seaside trade. The grounds are open 24/7, but buildings open on a seasonal schedule.

An informative and fascinating introduction to Salem's witchcraft hysteria, this museum offers a look at 1692 with 13 life-size stage sets featuring narration of what life was like at that time. There is also a 15-minute guided tour through the exhibit Witches: Evolving Perceptions, which describes witch hunts through the years, from Europe to America. Tickets are sold online exclusively. In winter, the museum might not open in bad weather, plus it closes for a couple of weeks in January for upkeep. Call ahead to confirm hours.

Dedicated by Nobel laureate Elie Wiesel in 1992, this quiet, contemplative space—an antidote to the relentless marketing of the merry-witches motif—honors those who died because they refused to confess that they were witches. A stone wall is studded with 20 stone benches, each inscribed with a victim's name, and sits next to Salem's oldest burying ground. Many people leave small tokens on the sites to commemorate the victims to this day. Six locust trees were planted to represent the injustice of the trials, as they are the last to bloom and the first to lose their leaves.

View artifacts from all facets of American life, put in social and political context. Specializing in the history of American Freemasonry and Fraternalism, the changing exhibits and lectures also focus on local events leading up to April 1775 and illustrate Revolutionary-era life through everyday objects such as blacksmithing tools, bloodletting paraphernalia, and dental instruments, including a "tooth key" used to extract teeth. Self-guided tours are free; you can opt for a one-hour guided tour for $6.

In a quiet Cape Ann town 32 miles north of Boston, this beach gets its name from the musical squeaking sound its gold-color sand makes when you step on it. The beach is popular with both locals and out-of-towners in summer, but parking is quite limited and near impossible for nonresidents. It's also worth a visit in fall, when the crowds have gone home and you'll have the splendid shores all to yourself. There's a snack bar at the beach, but it's worth taking a 10-minute stroll up Beach Street into town. The easiest, and cheapest, way to get here is by MBTA's Newburyport/Rockport Commuter Rail line from Boston's North Station to the Manchester stop, which is a 15-minute walk from the beach. From downtown Boston the train takes 45 minutes. Amenities: food and drink; lifeguards; showers; toilets. Best for: swimming; walking.

This garden cemetery on the National Registry of Historic Places served as a place of inspiration and a final resting place for American literary greats like Louisa May Alcott, Ralph Waldo Emerson, Henry David Thoreau, and Nathaniel Hawthorne. Each Memorial Day, Alcott's grave is decorated in commemoration of her death.

Consider a sail along the harbor and coast aboard the meticulously maintained 65-foot schooner Thomas E. Lannon, crafted in Essex in 1997 and modeled after the great vessels built a century before. Drinks and snacks are available for purchase. From mid-May through mid-October, the Ellis family offers two-hour sails, including trips that let you enjoy the sunset or music.

Nathaniel Hawthorne lived at the Old Manse in 1842–45, working on stories and sketches; he then moved to Salem (where he wrote The Scarlet Letter) and later to Lenox (The House of the Seven Gables). In 1852 he returned to Concord, bought this rambling structure called The Wayside, and lived here until his death in 1864. The home certainly appealed to literary types: the subsequent owner of The Wayside, Margaret Sidney, wrote the children's book Five Little Peppers and How They Grew (1881), and before Hawthorne moved in, the Alcotts lived here, from 1845 to 1848. Notably, The Wayside is a site on the National Underground Railroad Network to Freedom program, as the Alcotts helped at least one enslaved person on his way to Canada and freedom. An exhibit center, in the former barn, provides information about the Wayside authors and links them to major events in American history (open for special events). Hawthorne's tower-study, with his stand-up writing desk, is substantially as he left it.