Boston Common

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.

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).