Best of Boston

Best Family-Friendly Hike

Pleasure Bay Loop to Castle Island

South Boston

There’s something for every kid on this flat 2-mile stroll: a beach walk, some exciting maritime hiking on a narrow jetty where waves crash along [...] read more»

2022 Best Family-Friendly Hike

Great Blue Hill Trail, Blue Hills Reservation

Milton

Slightly challenging — yet mercifully short — bursts of uphill that give kids a sense of accomplishment. A tower to climb at the top. And, [...] read more»