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South Boston’s 6 must-visit sites

Awaiting adventures range from the historic to the whimsical, including the Lawn on D, the Dorchester Heights Memorial, and Castle Island

Photo by David L. Ryan/The Boston Globe via Getty Images

South Boston—a.k.a. Southie—is a supersized neighborhood that’s chock-a-block with triple-deckers, churches, and pubs.

Depending on whom you ask, it includes Fort Point, the Seaport District, West Broadway, City Point, and Telegraph Hill. And, with its deep Irish roots, the neighborhood is also home to the best St. Patrick’s Day celebrations (pre-coronavirus, of course). And there’s other stuff—lots of other stuff.

From museums to islands, here are South Boston’s six must-visit sites. (Check ahead, though, on each of these: The novel coronavirus pandemic led in mid-March to a state of emergency and a stay-at-home advisory for Massachusetts.)


Castle Island

Boston Daily Life Photo by Craig F. Walker/The Boston Globe via Getty Images

This historic 22-acre peninsula was an island before 1928. The first fort here was built in 1634; the current Fort Independence was built somewhere between 1834 and 1851. Edgar Allan Poe served a five-month stint in the military at Castle Island in 1827.

Open sunrise to sunset, it’s particularly popular when the weather warms up. Take a stroll around the shore at Pleasure Bay.

Institute of Contemporary Art

USA - Museums - The Institute of Contemporary Art Photo by James Leynse/Corbis via Getty Images

The Institute of Contemporary Art (ICA) knows nothing but change. Founded as the Boston Museum of Modern Art in 1936, it’s moved more than 13 times. It looks like it’s staying put in the neighborhood for a while, though. In addition to permanent collections by artists such as Yayoi Kusama, the building itself is also architecturally intriguing.

Diller Scofidio + Renfro’s 65,000-square-foot space was the first museum to be built in Boston in 100 years. Make sure to take in the view of the harbor through the floor-to-ceiling glass wall. Bonus: The museum is free on Thursdays from 5 to 9 pm.

Boston Children’s Museum

A waterfront pier is in the foreground. In the distance are a row of attached red brick apartment buildings. Shutterstock

This is a fun option for people with kids or childlike souls. If you’re on a budget and free on a Friday night, then head over to pay a mere $1 for admission from 5 to 9 p.m.

Fans of novelty architecture will appreciate the 40-foot milk bottle standing nearby. Ice cream maker Arthur Gagner built this wood structure in 1930. By the time he sold it to the museum in 1943, milk bottles had changed shape to the square box. In 1977, H.P. Hood and Sons bought it, rebranded it, and gave it to the museum. It’s been restored to its original purpose as an ice cream stand.

Lawn on D

Loving The Lawn On D Photo by Dina Rudick/The Boston Globe via Getty Images

On the east side of the Boston Convention and Exhibition Center is a relatively new public park that also serves as outdoor space for conventions and events. Open May through October, it has a rotating schedule of events. Swing Time is arguably the most popular attraction, where you can spin and sway on glowing circular swings for free.

Thompson Island

View Of Boston Skyline From Southwest Tip Of Thompson Island Photo by Aram Boghosian for The Boston Globe via Getty Images

This site forms South Boston’s south shoreline. One of the Boston Harbor Islands, its salt marshes, herons, egrets, and flowering meadows are an ideal place to observe nature. Its namesake is David Thompson, who moved to the island in 1626, four years before the Puritans arrived. Ferries are available on the weekends from June to October.

Dorchester Heights Monument

Dorchester Heights

Boston architects Peabody and Stearns built this white marble monument to commemorate a 1776 colonialist victory over the British. Located in the center of Thomas Park, the structure stands at 115 feet , so it’s hard to miss.

Once you make it to the top of the steep hill, you can see the Blue Hills and the Harbor Islands. This is on the National Register of Historic Places, and sits within the Dorchester Heights Historic District.

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