Best of Boston
2015 Best Hike, Family-Friendly
Dungeon Rock, Lynn Woods Reservation
If your kids are balking at the prospect of a walk, tempt them with a trek to this spooky site. A gentle one-mile round-trip walk takes you to a 174-foot cave, once a hiding spot for a 17th-century pirate. Go between 8:30 a.m. and 2:30 p.m., Tuesdays through Saturdays, when the park ranger props open the heavy iron door, then descend a wooden staircase and explore the tunnel within.