Castle Island and Pleasure Bay loop

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Castle Island and Pleasure Bay loop

Photo: Chris Wood (User:chris_j_wood). · CC BY-SA 4.0 · Wikimedia Commons

🏖️ Beach · Boston

2.5 hours · Free · No reservation needed

age fit
0–1 yr
★ 4.0
1–3 yrs
★ 5.0
3–5 yrs
★ 5.0
5–10 yrs
★ 5.0
  • 🚗
    About 25 min drive
    From Newton · Parking: Large free lot at the end of William J. Day Blvd, fills by midday on summer weekends
  • 🍼
    Stroller-friendly
    Flat surfaces — bring the stroller
  • 🌳
    Little shade
    Great on sunny days · Good on cool days · Handles heat · Wind-OK
  • ⏱️
    Typical visit: 2.5 hours
    Best seasons: Spring · Summer · Fall

The peninsula at the tip of South Boston: below old Fort Independence runs a 2-mile paved loop along the water, with planes taking off and landing low out of Logan on one side and the calm shallows of Pleasure Bay on the other, a playground at the foot of the fort, and hot dogs and fried clams at Sullivan's that are every Bostonian's summer memory.

💡 Tips
Fully accessible for strollers and scooters, and a 2-year-old can watch planes all afternoon. Pleasure Bay is shallow but has no lifeguards and the water is cold; for real swimming go to M Street Beach or Carson Beach next door. Sullivan's closes for winter (reopens around late February). Free fort tours on summer weekends.

What this place offers

✓plane watching
✓boat watching
✓fort
✓beach
✓paved loop
✓playground
✓Sullivan's hot dogs
✓restrooms

Featured in these guides

This weekend's weather in Boston

Forecast at the destination itself (coast and hills often differ from home)

🌧️
Sat 10/17
Rain · 41–62°F · 80% rain
🌤️
Sun 10/18
Partly cloudy · 40–58°F · 1% rain

Location

Boston, Massachusetts

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