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)33 results · “free” · 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)
A beloved independent bookstore with a serious author-event calendar and excellent staff picks.
Newtonville
4.9(288)Hemlock-shaded trails above a rocky river gorge, with a stone aqueduct arch that echoes fifteen times.
Newton Highlands
4.8(276)The city’s last working farm — a farmstand, kids’ programs, and 300 years of continuous cultivation.
Thompsonville
4.9(187)The classic Newton shot: a stone arch over a gorge, best in the last hour of light in October.
Newton Upper Falls
4.8(197)Meadows, woods and a canoe launch on the Charles — Newton’s premier birding spot at 180+ species.
Oak Hill
4.8(164)
A dead-flat grassy path along a buried 19th-century aqueduct, running for miles through backyards and woods.
Waban
4.7(121)A gentle Charles River cove with a sandy edge, big shade trees and one of Newton’s best-loved playgrounds.
Auburndale
4.7(96)One of the busiest public libraries in Massachusetts: huge children’s wing, museum passes, quiet study floors.
Newton Centre
4.9(508)67 acres of woodland loop trails, a cross-country course, and a Tuesday farmers market in season.
Newton Highlands
4.7(231)An open-air shopping block with big-name retail, a cinema, and better-than-average patio dining.
Chestnut Hill
4.4(287)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)
Eat on Washington Street, walk fifty feet to the cinema — Newton’s easiest night out.
West Newton
4.5(172)
Hop onto the paved riverside path here and ride all the way into Boston without a traffic light.
Newton Corner
4.6(143)Real bocce courts with real regulars — show up, watch a while, and you will get invited in.
Nonantum
4.7(86)A long, open slope that becomes the neighborhood sledding destination after every storm.
Oak Hill
4.6(94)
Grand Victorians, Shingle Style porches and Colonial Revivals on Newton’s most photogenic hill.
West Newton
4.6(94)
Three brunch spots within a block of the Washington Street rotary, none of them requiring a reservation.
Newton Corner
4.3(118)
Shaded modern play structures, a toddler section, and a splash pad in summer.
Newton Corner
4.5(88)Put in on the Charles’s quiet southern bend — no motorboats, no crowds, herons everywhere.
Oak Hill
4.7(61)Four striped courts, open play mornings, and a very welcoming regular crowd.
Auburndale
4.5(73)Quiet, rooty single-track through Newton’s biggest stretch of unbroken woodland.
Oak Hill
4.5(72)
A flat six-mile out-and-back on quiet streets and aqueduct paths, ending at coffee.
West Newton
4.5(66)
A Victorian-era pocket park with a pond, weeping willows and Newton’s oldest planted landscape.
Newton Corner
4.4(67)Over a hundred garden plots on a sunny hillside — open to walk through, with a waitlist to grow.
Oak Hill
4.6(55)A short, pretty riverside walk past old mill dams where the Charles drops toward Wellesley.
Newton Lower Falls
4.4(62)A pedestrian bridge over the Charles connecting Newton to Wellesley — great heron spotting at dusk.
Newton Lower Falls
4.6(47)Public hard courts with a backboard, rarely a wait outside weekend mornings.
Waban
4.3(57)A twenty-minute wooded loop that feels like a real hike to a five-year-old.
Waban
4.4(48)A quiet neighborhood playground that never feels crowded, with a full ball field beside it.
Newton Lower Falls
4.4(39)A flat two-mile residential loop linking the farm, Nahanton Park and Winchester Street.
Thompsonville
4.3(37)A self-guided loop past 19th-century mill housing, a 1811 church, and the old paper works.
Newton Lower Falls
4.2(33)