8 Best Sights in Boston, Massachusetts

Nothing is more central to the city than Boston Common, the oldest public park in the United States and undoubtedly the largest and most famous of the town commons around which New England settlements were traditionally arranged. Dating from 1634, the Common started as 50 acres where freemen could graze their cattle. (Cows were banned in 1830.) Don't confuse the Common with its sister park, the Public Garden, where the Swan Boats glide and flowers bloom three seasons of the year.

On its Tremont Street side, State House employees, downtown professionals, and tourists gather to take a break and enjoy lunch at one of food trucks parked (April through October) at the Brewer Fountain Plaza. A few steps away, the Freedom Trail starts in front of the Boston Common Visitor Information Center. The Common's highest point, near the Parkman Bandstand, was once called Flagstaff Hill and is now surmounted by the Soldiers and Sailors Monument, honoring Civil War troops. The Common's only body of water is the Frog Pond, a tame and frog-free concrete depression used as a wading pool and spray fountain during summer and for ice-skating in winter.

Central Burying Ground lends the park an eerie vibe at its site on Boylston Street; in fact, the Common boasts a fair amount of haunted history. Across from the State House, on the Beacon Street side, sits the splendidly restored Robert Gould Shaw 54th Regiment Memorial, executed in deep-relief bronze by Augustus Saint-Gaudens in 1897. In addition, this is Freedom Trail stop 1.

This 300-acre patch of remaining wetland environment is indicative of the salt marsh landscape that covered Boston when early settlers arrived and which today has been filled in. As you walk or run Belle Isle's gravel paths, listen to the sound of the marsh's diverse bird community, which includes the American kestrel, belted kingfisher, great blue heron, northern harrier, and saltmarsh sparrow. Boardwalks venture into the marsh for great viewing and photo ops.

For the last 30-plus years, a number of agencies and organizations have been collaborating to create a waterfront walking path along Boston's shoreline—currently, it stretches 43 miles. Boston's Seaport District boasts a hearty portion of the Harborwalk, which winds from the Fort Point Channel, around Fan Pier, up Seaport Boulevard, and out and around the Black Falcon Cruise Terminal. Along the way, pedestrians can see art exhibits, stationary viewfinders, open green spaces, and incredible Boston Harbor views. Marked signs point the way, and maps can be found online.

Although it once was, Castle Island is no longer, well, an island. Today, this tip of South Boston is accessible by car and by foot from Day Boulevard. Castle Island's centerpiece is Fort Independence, built in 1801 (although there have been battlements on-site since 1644) and open for free tours on summer weekend afternoons. Castle Island is a popular spot for South Boston residents to walk their dogs, jog, or cycle, whether just around the island itself or along the water-set Pleasure Bay Loop. There's also a nice playground for kids. If you get peckish, stop by Sullivan's (known locally as Sully's). Open February through November, come to this Castle Island institution of more than 60 years for a hot dog and fries. Views of the harbor and its outlying islands are expansive.

You've got to really look for the garage doors that mark the entrance to this zero-frills local taproom. Once you make it inside the industrial space, you can sample flights of Downeast's fresh, unfiltered cider varieties—many of which are only available at the cider house. Bring some food to eat if you want—none is served here—and your dog.

Near the corner of Beacon and Arlington Streets, the recently redone Arthur Fiedler Footbridge crosses Storrow Drive to the 3-mile-long Esplanade and the Hatch Memorial Shell. The free concerts here in summer include the Boston Pops' immensely popular televised July 4 performance. For shows like this, Bostonians haul lawn chairs and blankets to the lawn in front of the shell; bring a takeout lunch from a nearby restaurant, find an empty spot—no mean feat, so come early—and you'll feel right at home. An impressive stone bust of the late maestro Arthur Fiedler watches over the walkers, joggers, picnickers, and sunbathers who fill the Esplanade's paths on pleasant days. Here, too, is the turn-of-the-20th-century Union Boat Club Boathouse, headquarters for the country's oldest private rowing club. You can also access the park by crossing the Frances Appleton Pedestrian Bridge linking the Beacon Hill neighborhood to the Esplanade.