Nine Awesome Urban Hikes around Boston
Why trek all the way to Vermont when you can explore Boston’s hidden-in-plain-sight green spaces?
As city dwellers continue to search for ways to get outside close to home amid the disruptions of the pandemic, an emerging idea has taken root: You can go for a great hike in the middle of a city. And with its wealth of parks and urban wilds—parcels of preserved rustic greenery surrounded by city infrastructure—Boston offers a veritable smorgasbord of urban hikes. So this summer, fall, and beyond, discover the rugged side of the city by throwing some snacks in a backpack and going for a walk through one of these unsung green spaces.
D. Blakeley Hoar Sanctuary
Brookline and Chestnut Hill
Distance: 0.7-mile loop hike
Why go? A neighborhood secret at the nexus of Brookline and Chestnut Hill, D. Blakeley Hoar Sanctuary is a surprisingly rustic pocket of wilderness surrounded by homes that are equally as majestic. Winding boardwalks crafted from recycled plastics take you through tunnels of flora as the buzzing, chirping, and rippling of the sanctuary’s crown jewel—a stunning red maple swamp—drown out echoes of the roads nearby.
Don’t miss: The impressive “Roxbury Puddingstone” rock formations that run along the sanctuary’s north boundary (it’s the state rock of Massachusetts) and a mysterious “bridge to nowhere” that veers into the swamp—it once connected to trails in the neighboring Leatherbee Woods, which were destroyed by flooding.
Best for: Birders and families looking for a good starter hike along the short but scenic trails.
How to get there: The entrance to the sanctuary is located by the tennis courts at Baker School. Park on Beverly Road, enter the school driveway (a large sign for the sanctuary is posted here), and descend stairs to the tennis courts to reach the trailhead. You can also take the MBTA’s 51 bus to Independence Drive at Beverly Road.
Belle Isle Marsh Reservation
Distance: 0.6-mile loop hike
Why go? Once the site of a drive-in movie theater in Eastie, Boston’s last remaining salt marsh has been restored to its natural state, making it a reliable stopover for birds such as ospreys and sandpipers. The gentle, flat loop path through the marsh features boardwalks that lead to viewing platforms, allowing you to get into the thick of the green, reedy understory of the wetlands with your camera or binoculars.
Don’t miss: The panoramic views of downtown Boston and the harbor from the viewing platforms along the path will make you the envy of your Instagram followers. As you head toward the wooden open-air observation tower at the north end of the marsh, look across the nearby meadows to spot blooming yellow mustard flowers.
Best for: A wide range of visitors—including hikers with mobility limitations—thanks to the smooth, level trails.
How to get there: You can reach the reservation by taking the MBTA Blue Line to Suffolk Downs station and walking northwest along Bennington Street to the reservation entrance. Ample parking is also available at the trailhead.
Jamaica Plain and West Roxbury
Distance: 1.6-mile loop hike
Why go? As the Arnold Arboretum’s shaggier (but no less picturesque!) next-door neighbor, Allandale Woods is one of Boston’s larger urban wilds. Fittingly, the 86 acres offer a constellation of rocky root-festooned trails that take hikers past old stone walls, over wooden footbridges, and beside ponds with lily pads worthy of a French impressionist painter.
Don’t miss: All kinds of natural and artificial wonders dot the landscape, from vernal pools where frogs spawn and sing to an old springhouse where former landowner Henry W. Wellington tapped water from a natural spring.
Best for: Novice hikers seeking a reprieve from city life.
How to get there: Public transit riders can take the MBTA’s 38 bus to Centre Street at VFW Parkway. A path accompanied by a posted trail sign enters Allandale Woods here. If you’re driving, park near the intersection of Leland and Crehore roads and then walk to the southern end of Leland, where another signed trail descends into the woods.
Pleasure Bay Loop to Castle Island
Distance: 2.1-mile out-and-back hike
Why go? It’s not often that you get to walk across an expanse of water, but the sea-breeze-scented hike to Castle Island is an exception. Joining up with the Boston Harborwalk (which runs 43 miles from Dorchester Bay all the way to Eastie), the hike kicks off with a pleasant amble on the beaches at Pleasure Bay. Then things take a dramatic turn as the path veers east onto a narrow stone jetty that juts out into the whitecapped harbor waters before curving northeast and arriving at Fort Independence.
Don’t miss: The harbor views from the jetty and the sight of waves crashing against the rocks are the epitome of maritime hiking. When it’s over, treat yourself to a brisk dunk in Pleasure Bay.
Best for: Inquisitive kids and history buffs alike will be impressed with Fort Independence’s massive stone walls.
How to get there: Parking is available next to Fort Independence in a designated lot, and the MBTA’s 7, 9, and 11 buses offer direct access to Pleasure Bay. Disembark at Farragut Road opposite 2nd Street, walk southeast across Evans Field and William J. Day Boulevard, and begin your hike from the beach.
Skyline Park to Lost Pond Sanctuary and Kennard Conservation Area
Brookline and Newton
Distance: 3.2-mile loop hike
Why go? Once the site of a town landfill, Skyline Park is a gleaming example of what a restored green space can look like. Meandering paved paths climb a breezy and exposed hillside to reach a lovely viewpoint of the Brookline and Newton woods. From there, things get muddier as you follow a dirt path over footbridges into the adjacent forests of Lost Pond Sanctuary and Kennard Conservation Area, where peat moss bogs and wildflowers await.
Don’t miss: Woodland views from the hilltop of Skyline Park kick things off on a high note before you reach Lost Pond’s “quaking bog,” where the ground gently wobbles from visitors’ footsteps. From there, keep an eye out for fern marshes and smoky volcanic rock outcroppings in the Kennard forest.
Best for: Families with curious kids—or leashed dogs.
How to get there: There are two parking lots in Skyline Park. Or, begin your hike in Kennard Conservation Area by parking on Pond Brook Road, where a trailhead is located at the end of the street.
Franklin Park Loop
Roxbury, Dorchester, and Jamaica Plain
Distance: 2.3-mile loop hike
Why go? Whether you’re poking around abandoned bear cages or the stony remnants of an athletic field house, a loop hike through Franklin Park sometimes feels like wandering into an episode of Lost. Designed by visionary landscape architect Frederick Law Olmsted, the green space boasts a labyrinth of paths that meander through a deciduous forest to vine-ensnared ruins of relics past.
Don’t miss: Climbing the winding stone staircases into “The Wilderness” on the park’s west side before proceeding to the aforementioned field-house ruins and the old “bear den” cages near White Stadium.
Best for: Literal and spiritual eight-year-olds—not to mention Atlas Obscura fans—will love exploring the park’s quirkier artifacts.
How to get there: Forest Hills MBTA station is half a mile from the park. Walk east along Arborway from the station and turn left after crossing Circuit Drive to enter the southern end of Franklin Park. Free parking is available in several lots within the park, including in the zoo lots.
Stony Brook Reservation
Hyde Park and Roslindale
Distance: 2.8-mile loop hike
Why go? A shadowy expanse of hardwoods, Stony Brook Reservation is a quieter alternative to the city’s more heavily trodden urban forests, boasting a network of rugged paths that sidewind through old trees and boulders. The reservation’s centerpiece, Turtle Pond, is the source of Stony Brook—the namesake stream that trickles through the woods before disappearing into a pipeline and flowing for miles beneath Boston.
Don’t miss: The dock at Turtle Pond offers memorable vistas, as do the blooming wetlands near the reservation’s northernmost entrance.
Best for: Solitary hikers, families, and wildlife enthusiasts alike (just be sure to wear closed-toe shoes while exploring the rougher and rockier trails).
How to get there: From Forest Hills MBTA station, take the 34 or 40 bus to Washington Street at West Roxbury Parkway. A short dirt path from a shopping plaza lot leads to Blue Ledge Drive and Stony Brook Reservation’s northernmost entry gate. Parking is available along Enneking Parkway in small pull-outs that offer trail access.
Emerald Necklace Traverse
Distance: 7.8-mile one-way hike
Why go? Frederick Law Olmsted not only designed many of Boston’s best parks, but also laid them out in the shape of an “Emerald Necklace” draped around Boston. Today, you can walk from Franklin Park to Boston Common along a chain of urban green spaces connected by trails and short street walks (print out a map from the Emerald Necklace Conservancy website before setting out). This epic journey through the city’s parks and wilds is best paired with recharge stops at restaurants along the way. When it’s over, you can gaze out at the Boston Public Garden from Flagstaff Hill—ideally at dusk—before taking the subway back to where you started.
Don’t miss: The winding path to the top of Bussey Hill in Arnold Arboretum offers a tantalizing glimpse of downtown Boston—your destination. And from Olmsted Park to the Fenway Victory Gardens, you’ll find beautiful footbridges, cascades, and even sculptures along the Muddy River.
Best for: Those who want a hike they’ll really feel the next morning—without the two- to three-hour car ride north.
How to get there: To begin your traverse from Franklin Park, take the Orange Line to Forest Hills station. Walk east on Arborway to the park entrance. (Parking is also available at lots in Franklin Park.) At the trail’s end, near Boston Common, Park Street and Downtown Crossing stations will connect you to the Red, Orange, and Green lines.
Neponset River Greenway
Mattapan and Dorchester
Distance: 8.7-mile out-and-back hike
Why go? New England is where whispering woods meet the ocean, and on the Lower Neponset River Trail, you can hike through a gorgeous transitional zone between these environments. Heading east from Mattapan station, the paved, mostly level greenway follows Boston’s southern boundary river as it snakes through deciduous forests near Lower Mills to the sweeping coastal wetlands of Dorchester Bay.
Don’t miss: After passing through the arches of the Harvest River Bridge, look for a cascade on the river near Lower Mills. On the return journey, if you’ve still got some gas in the tank, veer right onto Butler Street where it crosses the trail to explore the gentle wooded paths of Dorchester Park.
Best for: Anyone who’s swooned over a coastal landscape painting, as well as birders and families who are experimenting with longer day hikes.
How to get there: The MBTA’s Mattapan trolley services the greenway with several stops. Begin your hike from Mattapan station, where the trail crosses the train tracks and the river on a long, sloped boardwalk. Street parking is also available near the station on residential side streets.