Boston’s largest park occupies land that was once a community cow pasture right in the middle of town. It’s a great jumping-off point for exploring Beacon Hill or Newbury Street (not to mention that it’s the starting point for the Freedom Trail), but the park itself also justifies its own trip. Take littles to check out the Make Way for Ducklings statue—based on Robert McCloskey’s famous children’s book—or for a ride on the unabashedly fun swan boats, which occupy the small lake in Boston Public Garden. In the winter, the frog pond on the northern edge of the Common hosts ice-skating. A visit to the original Cheers is also a cheesy but worthwhile outing for nostalgic grown-ups.
Chatham Lighthouse Beach
While you really can’t go wrong with any of the beaches along either Cape Cod Bay or the Atlantic Ocean side, this particular one, at the foot of a historic lighthouse, is unique in that you can swim (or wade) out to a beautiful sandbar where locals like to set out picnics and barbeques. While the surf can be too intense for the littles to handle on certain days, the beach is great for long seal-spotting strolls and shell-collecting expeditions. Fair warning: parking can be a pain, so consider biking.
4 Yawkey Way, Fenway
There is nothing more Boston than walking down Yawkey Way on game day. Even if you’re not a baseball fanatic, Fenway can make you feel like one for a few hours. The stadium, which was originally built in 1912 and then reconstructed in 1934, is arguably the most historic in the MLB. Bonus points if you see a home run over the Green Monster while you’re there. If nothing is on the schedule while you’re in town, keep in mind that they still offer tours on non-game days, where you can go up in the Green Monster and peek into the locker rooms.
Harvard’s quintessentially New England campus is a pretty ideal place for strolling, particularly if you have a high schooler in need of a bit of motivation. While there, check out the collection at the Peabody Museum of Archaeology and Ethnology, which is housed in a quaint old building, and the Harvard Museum of Natural History, which is famous for its gorgeous glass flower replicas: Both are open to the public. When you’ve had your fill of the campus, tool around in Harvard Square—restaurants, shopping, street performers galore—and then take a walk along the Charles River, where you’ll find the boathouses for the sailing and rowing teams of all the local universities.
25 Harbor Shore Drive, South Boston
Originally an incubator for MoMA, the establishment officially became the Institute of Contemporary Art in 1948. It’s dedicated to identifying new artists and showing contemporary works in all mediums—including performance, film, and literature. What’s little known yet fascinating about the ICA is that the museum has introduced many of the most influential twentieth century artists, like Georges Braque and Edvard Munch, to US audiences. Aside from the stellar permanent collection, what keeps locals coming back is provocative exhibits in line with the cultural and political landscape. Currently on show are Caitlin Keogh’s investigation into gender and representation through large-scale paintings and Kenyan-born artist Wangechi Mutu’s A Promise to Communicate, an installation of the grey rescue blankets used in humanitarian relief efforts around the world.
Lighthouse Mini Road Trip
Starting at Chatham and driving up the cape to the Easternmost tip of Provincetown—and stopping at the historic lighthouses along the way—is an iconic New England experience. While some are closed to the public, many will have staff on hand to share historically significant tidbits and even take you for a look inside. Best of all, there’s no need to pack a lunch: Each town you’ll pass will have plenty of can’t-go-wrong seafood shacks to choose from, where you can also always find the requisite soft-serve.
Minute Man National Historic Park
174 Liberty St., Concord
Every year on Patriots' Day (which is a statewide holiday in Massachusetts), the Lexington Minute Men stage a major reenactment of the Battle of Lexington on the Lexington green. Waking up early to fully experience the drama is something of a rite of passage for kids growing up in Boston. Whether or not you’re there for Patriots' Day, Minute Man National Historic Park has a lot to offer—visitors can take tours of historic homes lining the fields, kids can try on historic clothing, and the historic Wayside, which was home to authors like Louisa May Alcott, is open for exploring. Be sure to visit Buckman Tavern, where you can see the tavern’s original door and the musket bullet that’s still lodged in it.
Walk the Freedom Trail
In 1951, the citizens of Boston preserved and dedicated the historic Freedom Trail, a two-and-a-half-mile walk through the city that passes sixteen historically significant sites, starting with Boston Common and ending with the USS Constitution. While the Freedom Trail Foundation offers tours—led by guides in colonial outfits, no less—it’s actually more fun to grab a map and do a self-guided version, as the red line marking the trail’s path throughout the city makes it all but impossible to get lost. Just make sure you don’t miss the Old State House (where the Declaration of Independence was first read to the people of Boston in 1776), Paul Revere’s House, and Old North Church (where Robert Newman famously hung two lanterns in the belfry, alerting Revere that the British were coming over the Charles River).
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