Castle Island Playground

Castle Island in South Boston is one of the most beloved family destinations in the entire Boston area — and the playground here is just one reason families make the trip. The combination of a waterfront park, a historic fort, an iconic clam shack, and an excellent playground creates a full family day without paying a single admission fee (for the park, at least).

The playground itself is well-designed with solid climbing structures, slides, and equipment appropriate for children ages 2-12. But the setting is what elevates Castle Island beyond a routine park visit: the playground sits with direct views of Boston Harbor and the South Boston coastline, with Logan Airport's flight paths passing directly overhead. For children who love planes, the low-altitude approaches over the harbor are genuinely thrilling.

The paved loop around historic Fort Independence is completely flat and stroller-friendly — one of the nicest waterfront walks in Boston, with harbor views on all sides and the city skyline visible across the water. Fort Independence itself is open for free tours during summer months, adding a history dimension for older kids.

Sullivan's restaurant at the entrance to Castle Island has operated since 1951 and is as much a part of the experience as the park itself. The clam chowder, hot dogs, lobster rolls, and ice cream are all consistently excellent. Lines can be long in summer but move quickly. Check whether they accept credit cards before you go — cash has historically been preferred.

Parking in the Castle Island lots fills extremely quickly on summer weekend mornings. Arrive before 9am to get a spot easily. Street parking in South Boston is the fallback but requires a walk. The park is also reachable by MBTA bus (Route 7 from South Station area).

Fully free admission to the park and playground. Budget $15-25 per family for Sullivan's.