Chestnut Hill Reservoir Loop
A flat 1.5-mile gravel loop around open water, with the Boston skyline on the far side.
Chestnut Hill
4.8(412)8 results · “walking” · 2026-09-12 to 2026-09-13
A flat 1.5-mile gravel loop around open water, with the Boston skyline on the far side.
Chestnut Hill
4.8(412)The city’s last working farm — a farmstand, kids’ programs, and 300 years of continuous cultivation.
Thompsonville
4.9(187)
A dead-flat grassy path along a buried 19th-century aqueduct, running for miles through backyards and woods.
Waban
4.7(121)Collegiate Gothic towers, a hilltop reservoir view, and a reading room that looks like a cathedral.
Chestnut Hill
4.7(168)A flat, paved rail-trail through the old mill district, with public art and a mile of easy walking.
Newton Upper Falls
4.6(158)
Grand Victorians, Shingle Style porches and Colonial Revivals on Newton’s most photogenic hill.
West Newton
4.6(94)A short, pretty riverside walk past old mill dams where the Charles drops toward Wellesley.
Newton Lower Falls
4.4(62)A flat two-mile residential loop linking the farm, Nahanton Park and Winchester Street.
Thompsonville
4.3(37)