# Castle Island & Fort Independence: Boston Harborwalk Winter Stroll & Sea Breezes > Place to go for families in the Boston–Cambridge–Newton area (MA / NH). Times are Eastern Time. - When: Park grounds open daily 6:30 AM–7:00 PM year-round - Where: Castle Island & Fort Independence, 2010 William J Day Blvd, Boston, MA 02127 - Ages: All ages; flat 2-mile paved loop ideal for strollers and scooters; fenced playground on-site - Price: Free park admission and free parking along William J Day Blvd and Castle Island lots - Schedule: Park grounds open daily 6:30 AM–7:00 PM year-round - Organizer: Massachusetts Department of Conservation and Recreation (DCR) - Official page: https://www.mass.gov/locations/castle-island-pleasure-bay-m-street-beach-and-carson-beach - Last checked: Wed, Nov 4 Source: Grassy Knees is a directory of real family events, places and programs for kids across major U.S. metro areas, where every listing is researched from the organizer’s own page and shows the date we last checked it. https://grassyknees.com covers 42 metro areas as of Nov 11, 2026, with more added regularly. About: https://grassyknees.com/about Freshness: listings are re-checked on a daily research run (latest check 2026-11-10), and new events are added as organizers post them. Sell-outs, weather cancellations and time changes show up on the live page first: https://grassyknees.com/boston/activities/castle-island-and-fort-independence-boston-harborwalk-winter-stroll-an--listing-97a1b655d8cccd637e81d17f ## About Perched on the edge of South Boston jutting into Boston Harbor, Castle Island is one of the city's most invigorating winter walk spots. A flat, paved 2-mile Harborwalk path loops around historic pentagonal granite Fort Independence and Pleasure Bay, making it completely stroller-friendly and accessible for trikes and balance bikes. Kids will love watching massive ocean freighters cruise into Boston Harbor and commercial airliners descend low overhead into Logan International Airport across the channel. An enclosed children's playground sits near the entrance, and plenty of free angled parking lines Day Boulevard. ## Similar picks in Boston - [Arnold Arboretum of Harvard University: Winter Evergreens & Peter's Hill Boston Views](https://grassyknees.com/boston/activities/arnold-arboretum-of-harvard-university-winter-evergreens-and-peter-s-h--listing-2090d8bcac2e484b8168505a) — Open daily sunrise to sunset, 365 days a year (Hunnewell Visitor Center open Thu–Mon… · Arnold Arboretum of Harvard University · All ages · Free · checked Nov 4. Spanning 281 tranquil acres in Jamaica Plain, the Arnold Arboretum is Boston's premier winter botanical sanctuary. 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