Diversions: Family-Friendly Hikes In and Near West Roxbury

Michael Loconto
6 min readMar 10, 2021


If your family is like ours, you have spent much of the last year getting to know the paths and trails close to home. After a long day of remote work and learning, we try to get out most afternoons (and away from screens) for an hour or two of fresh air. On weekends, we also try to roam a bit further afield.

If you need a starter list, or some new suggestions to add to your routine, here are some of my favorite walks and hikes in and around the Parkway. These walks are geared toward families, but are safe and accessible for all ages. Most trails in and around the neighborhood can be accessed without a car ride, and those that are a bit further from home generally require less than a 30-minute drive (eliminating the need for stops in between).

If you have other suggestions, please add them in the comments below — and happy trails!

Stony Brook Reservation (West Roxbury / Roslindale). Our go-to destination is Stony Brook, which has a bit of everything. Within a 15-minute walk from most locations in West Roxbury and Hyde Park, you can quickly plunge into nature and escape traffic and the noise of city life. The water tower and park atop Bellevue Hill is part of the reservation, with three paved paths maintained across and around the peak. There is also a wooded trail, the Kennedy path, maintained by neighbors. Across Washington Street, you can enter the reservation from a number of marked points along Enneking and Turtle Pond parkways and Smithfield Road. Choose from a roughly three-mile paved path that loops around the park behind the George Wright golf course, or a number of marked trails that follow the rocky outcrops throughout the park — with some steep ascents that provide views toward the Blue Hills, and a path around Turtle Pond and its dual docks.

Allandale Woods (West Roxbury / Jamaica Plain / Brookline). The City of Boston’s Urban Wilds program has taken on a number of trail upgrades in the woods in recent years, with access points on the West Roxbury and VFW parkways, as well as Allandale Road and Centre Street near the Faulkner Hospital and Annunciation Hall. My kids love the small stream that runs through the wild and walking atop the stone wall that extends throughout the property. In the wet season, there are a number of waterfalls and babbling brooks that extend from Rock Pond and the vernal pools on site. Parking is available at Annunciation Hall in marked spaces.

The Arnold Arboretum of Harvard University (Roslindale / Jamaica Plain). Most people know this popular spot for Lilac Sunday on Mother’s Day each May, and the leisurely paved paths and marked trails amidst hundreds of trees and plants from across the globe. For us, the view atop Peters Hill is great anytime of day, with the skyline to the east and Newton and Cambridge to the north, and Blue Hills to the southwest. What has been a find in this recent era of (extreme) social distancing are the trails along Hemlock Hill, off Bussey Street and above the brook that runs along the Valley Road path inside the park. My kids have also enjoyed walking atop the drain pipe that runs through the marsh opposite the Hunnewell Building at the main entrance.

Hancock Woods and the D. Blakeley Hoar Nature Sanctuary (Brookline). Accessible behind the Baker School off Beverly Road and Hancock Village along Independence Drive, the nature sanctuary is a tranquil 1.1 mile loop featuring multiple extended boardwalk sections. There are some hills and plains and a pine forest for variety as well. If you walk from West Roxbury, you can make your way over to the sanctuary through Hancock Woods. A number of unmaintained trails exist off of the VFW Parkway (we typically use the steep rock path adjacent to Keane Road), and there is marked entry point behind the Atrius Health building across from Bertucci’s at the intersection of the parkway and Independence Drive. There are a number of great rock scrambles deep in these woods, but keep an eye out for broken glass.

Millennium Park and Cutler Park Reservation (West Roxbury / Dedham / Needham / Newton). Families are also well acquainted with Millennium Park after spending many a Saturday atop the soccer fields, but the trails that lead off from the rear of the property and into Brook Farm and the adjacent cemetery are peaceful and uncrowded. Pair this walk with the Cutler Park Reservation, which follows the Charles River into Needham and Newton. Entering the park in Dedham from Great Plain Avenue, at the parking area just off Route 128, hikers quickly descend to an aging boardwalk that runs deep into the reservation. There is a pedestrian tunnel under the railway tracks for the commuter rail’s Needham Line, with a path that continues toward the parking area off Kendrick Street in Needham. This trail is frequented by dog walkers, trail bikers and runners, and is suitable for advanced hikers that can move around some of the muddier and less maintained portions of the trail.

In the City

Emerald Necklace (Jamaica Plain / Brookline / Fenway). While Jamaica Pond, Franklin Park and the Esplanade are popular destinations along the Olmstead park system, we frequently find ourselves making the brief loop that runs along the Muddy River from Brookline Avenue near the hospitals along the Riverway and the Fenway past the Museum of Fine Arts and into the Victory Gardens at Charlesgate. Kids love the bridges across the river and brooks in the Fens and adjacent to the Longwood stop on the D branch of the Green Line (where free on-street, two-hour parking is ample), and there are plenty of options nearby for an outdoor snack ( Tasty Burger on Boylston Street is our usual stop).

To the West

Broadmoor Nature Sanctuary (Natick). Run by MassAudubon, Broadmoor requires timed ticketing to enter the property, which runs throughout a diverse ecosystem of marshland, waterfalls, high plains, and a section along the upper Charles River. It is a great place to spend a half-day with small crowds, and in the season provides an excuse to stop at Lookout Farm down the street for cider donuts on the way home.

Noanet Woodlands, Powisset Farm, Rocky Woods and the Hale Reservation (Dover / Westwood / Medfield). Throughout the pandemic, our long hikes have taken us out to the Noanet Woodlands in Dover, just off Route 109 and a 20-minute drive from the Parkway. The Trustees maintain the woodlands with well-marked trails and a network that connects to its other adjacent properties at Powisset Farm and Rocky Woods. Hale Reservation and its extensive network of trails and waterways is also accessible from the Farm and the Woodlands. Park at the Farm off Powisset Street (note: farm parking is free and always available, while the lot at Noanet is $5 per car and often full) and start with a visit to the pig pen with the kids before making off across the field for a connection to the Noanet trails, or using the farm’s own trail network to find connections to Hale and Rocky Woods at the rear of the property. One of our favorite finds of this season has been the woodchuck and beaver work evident across the Hale Reservation (pictured above), along with views of the city atop Noanet and the peaceful brooks across the property.

Hemlock Gorge Reservation (Newton Upper Falls). This spot packs a lot of terrain into a compact space, with parking just off Routes 9 and 128 on the Newton side of the gorge and along Elliott Street at Cook’s Bridge in Needham. The highlights include Echo Bridge, an aqueduct looming high over the Charles River and falls below, a series of locks just before the river disappears below Route 9, and an island accessible by a small wooden footbridge.

Blue Hills Reservation (Milton / Canton). Most know the Blue Hills Reservation for the Trailside Museum, the weather observatory atop the peak and the ski slope along Route 138 in Milton. If you can manage to snag a parking space (and pack lunch), make time to walk the Skyline Trail that extends through the reservation from the peak and observatory toward Route 28 in Randolph. With steep ascents, rocky scrambles, and well-marked trails, you can get in a lot of scenery changes in the span of an afternoon. The trails around Houghton’s Pond, off Blue Hills River Road (with access from I-93) and Hillside Street, are also less traveled and feature some nice rest areas near the water.

What are your favorite spots for local hikes? Add your suggestions in the comments. Michael Loconto lives in West Roxbury with his wife and three daughters, and hikes across New England and the Northeast.

Originally published at https://patch.com on March 10, 2021.



Michael Loconto

Arbitrator and mediator for the modern workplace. Attorney with limited practice in commercial contracts, data privacy and select compliance issues.