THE WALKING CITY TRAIL

Bridging 17 Boston neighborhoods from the Neponset River Reservation to Bunker Hill Monument, the Walking City Trail is a 27-mile urban walking path through some of Boston's most scenic and immersive parks, urban wilds, gardens, and residential neighborhoods. It was created in 2022 by a hearty crew of Boston ramblers inspired by similar park-to-park trails across San Francisco, Worcester, and Berlin. A showcase of Boston’s green space ecosystem, its unique built environments, and the hidden passages between them, the “WCT” is a public transit-accessible trail.

The Walking City Trail is divided into 4 sections that range from around 6 to 8 miles each. You can also split each trail section into two shorter hikes. You can hike the Walking City Trail in pieces of any size, or attempt to walk the whole thing over one epic weekend. And when you’ve completed the entire trail, be sure to let us know so that we can send you a free finisher’s patch that features the trail logo!

SECTION 1. NEPONSET RIVER RESERVATION, EDGEWATER GREENWAY, SHERRIN WOODS, CONNELL FIELD, STONY BROOK RESERVATION, SHERMAN STREET GREEN SPACE CONSERVANCY (8.3 MILES)

Set off from the Harvest River Bridge and follow the Neponset River through dense woodlands before reaching an even vaster urban forest that features one of the finest ponds in the city. It all ends with an epic view of the Downtown Boston skyline from the tallest hill in Boston and a final winding descent to a little-known *fairy village.*

SECTION 2. ADAMS PARK, ARNOLD ARBORETUM, BUSSEY BROOK MEADOW, SOUTHWEST CORRIDOR PARK, FRANKLIN PARK, CHILCOTT GRANADA GARDEN, PARLEY VALE WOODS, JAMAICA POND (5.7 MILES)

Kick off this double feature of serene, sculpted Olmsted parks by climbing through the arbor sanctuary of Arnold Arboretum for another sublime Boston vista from the top of Peters Hill. Then, walk along Bussey Brook to and through Southwest Corridor Park to "The Wilderness" of Franklin Park and eventually, to Jamaica Pond.

SECTION 3. JAMAICA POND, OLMSTED PARK, NIRA ROCK, MCLAUGHLIN WOODS, MISSION HILLTOP, KEVIN W. FITZGERALD PARK, THE RIVERWAY, THE FENS, FENWAY VICTORY GARDENS, COMMONWEALTH AVENUE MALL (6.1 MILES)

Puddingstone, chuckling creeks, and towering deciduous trees collide with staircases, back alleys, and built landmarks as the Walking City Trail follows the core of the Emerald Necklace linear park system (plus a hilltop deotur) to arrive at the Charles River Esplanade Park.

SECTION 4. ESPLANADE PARK, BOSTON PUBLIC GARDEN, BOSTON COMMON, AUNTIE KAY AND UNCLE FRANK CHIN PARK, MARTIN’S PARK, BOSTON HARBOR WALK, PAUL REVERE MALL, CHARTER STREET PARK, PAUL REVERE PARK, WINTHROP SQUARE, BUNKER HILL MONUMENT (7.3 MILES)

Experience some of Boston’s most well-known historic landmarks through a new lens as the trail snakes through downtown green spaces and blue spaces to reach a moving footbridge crossing at the Charles River and finally, the climatic ascent to the Bunker Hill Monument!

Ready for a walk? Below you’ll find all of the resources that you need to go for an eye-opening journey on Boston’s Walking City Trail; from original trail maps to written directions and public transit connections.

TRAIL MAPS

Digital maps are the primary guiding resource for the Walking City Trail. The simplest and most familiar map option for a lot of walkers will be our Google Map of the entire Walking City Trails network. The Walking City Trail, the City On The Hills Trail, and any future trails to come will be featured on our Google Map.

What Google Maps offers in familiarity it can sometimes lack in specificity. Not all of the trail junctions in parks appear on Google Maps. For the most detailed maps of the Walking City Trails, we offer AllTrails maps of each trail; full maps and section maps! You can use these GPS-enabled maps with the free AllTrails app on your phone. Click any of the map links below to get started!

You can also download and print these section maps of the Walking City Trail. Each map is 3-4 pages long, in order to allow for closer views of the trail.

Walking City Trail - Section 1 (Printable Map)
Walking City Trail - Section 2 (Printable Map)
Walking City Trail - Section 3 (Printable Map)
Walking City Trail - Section 4 (Printable Map)

TRAIL DIRECTIONS

Sometimes it’s nice to pair maps with a secondary source for navigation. To that end, we have created turn-by-turn directions for the Walking City Trail that include plenty of information about public transit and food connections that you can avail yourself of, mid-walk.

Walking City Trail - Section 1 Directions
Walking City Trail - Section 2 Directions
Walking City Trail - Section 3 Directions
Walking City Trail - Section 4 Directions

TRAIL CONDITIONS

The Walking City Hills Trail is 27.4 miles long with roughly 1,400 feet of vertical elevation gain from start to finish. The trail surfaces include sidewalks, dirt paths, gravel paths, rocky and rooty paths, stairs, boardwalk segments, and bridges. Section 1 is the longest section of the trail, Section 2 is the hilliest and shortest section of the trail, and Section 4 is the most level section of the trail (save for Bunker Hill.)

PUBLIC TRANSIT

You can connect to each section of the Walking City Trail by using the MBTA transit system. Below you'll find transit connections to each section trailhead. In the written directions for each trail section, there are additional transit connections added for the "halfway" points near the middle of the trail’s five sections. In other places, you will have to go rogue and venture off-trail to reach local buses or trains.

​​Section 1 trailhead, Harvest River Bridge (Mattapan)
- Bus lines: 24, 28, 30, 31, 33, 245 
- Trolley: Mattapan Trolley at Capen Street Station 

Section 2 trailhead, Adams Park (Roslindale)
- Bus lines: 14, 30, 34, 35, 36, 37, 40, 51
- Commuter rail: Needham Line at Roslinvale Village Station

Section 3 trailhead, Jamaica Pond boathouse (Jamaica Plain)
- Bus lines: 39, 41
 - Subway: Orange Line at Green Street Station

Section 4 trailhead, Esplanade Park entrance on Mass. Ave (Back Bay)
- Bus lines: 1
- Subway: Green Line at Hynes Convention Center Station

Trail's end at Bunker Hill Monument (Charlestown)
- Bus lines: 92, 93
- Subway: Orange Line at Community College Station

WHAT TO PACK

One of the most underrated perks of taking a hike through a city is that you don't need to pack as much gear for your hike as you would in the backcountry, and the gear that you should bring won't cost nearly as much as backcountry gear. Usually this means that you'll be hiking with a lighter daypack. And if you do happen to leave something behind, chances are you can find it in a store near the trail. That said, an urban hike on the Walking City Trails network will be more enjoyable if you pack the following items...

​- Comfortable walking shoes and thick socks
- An extra pair of socks, just in case
- Sunblock and a season-appropriate hat
- At least 1 liter of drinking water
- Trekking pole(s) for stability on sloped surfaces
- 3 upper body layers, such as a t-shirt, a fleece, and a rain jacket
- A first aid kit with bandages and blister tape
- A headlamp or flashlight, if you're hiking into the evening or before sunrise
- A portable phone charger/battery, if you plan to navigate with your phone

TRAIL SIGNAGE

Urban trails like the Walking City Trails pass through green spaces that are managed by multiple entities, which can make obtaining permission for installing trail signage a long process. But we’re getting there! With tacit (not formal) approval from the City of Boston, we have installed 60+ weatherproof trail signs along the Walking City Trail. They serve as gateways to the digital trail maps and written directions. Some of these signs have been removed but most of them are still out there.