TRAIL MAPS
Digital maps are the primary guiding resource for the Walking City Trails. The entire network is featured on our Google Map, and we also offer individual trail maps on AllTrails, as well as GPX trail map files that you can download for use on other apps. (See the links below to access these interactive trail maps.)
What Google Maps offers in ease of use it can lack in specificity. Not all of the trail junctions in parks will appear on Google Maps. And since the Boston Boundless Trail traverses some rather big green spaces, such as the Blue Hills Reservaation, we strongly recommend pairing the Google Map with our written turn by turn directions (also available below) to avoid getting lost!
Boston Boundless Trail - Full Trail (AllTrails Map)
Boston Boundless Trail - Section 1 (AllTrails Map)
Boston Boundless Trail - Section 2 (AllTrails Map)
Boston Boundless Trail - Section 3 (AllTrails Map)
Boston Boundless Trail - Section 4 (AllTrails Map)
Boston Boundless Trail - Section 5 (AllTrails Map)
Boston Boundless Trail - Section 6 (AllTrails Map)
Boston Boundless Trail - Section 7 (AllTrails Map)
Boston Boundless Trail - Section 8 (AllTrails Map)
Boston Boundless Trail - Section 9 (AllTrails Map)
Boston Boundless Trail - Section 10 (AllTrails Map)
Boston Boundless Trail - Section 11 (AllTrails Map)
Boston Boundless Trail - Section 12 (AllTrails Map)
Click here to download a GPX file of the full Boston Boundless Trail map for use with other GPS apps.
You can also download and print these section maps of the Boston Boundless Trail. Each map is 3-4 pages long.
Boston Boundless Trail - Section 1 (Printable Map)
Boston Boundless Trail - Section 2 (Printable Map)
Boston Boundless Trail - Section 3 (Printable Map)
Boston Boundless Trail - Section 4 (Printable Map)
Boston Boundless Trail - Section 5 (Printable Map)
Boston Boundless Trail - Section 6 (Printable Map)
Boston Boundless Trail - Section 7 (Printable Map)
Boston Boundless Trail - Section 8 (Printable Map)
Boston Boundless Trail - Section 9 (Printable Map)
Boston Boundless Trail - Section 10 (Printable Map)
Boston Boundless Trail - Section 11 (Printable Map)
Boston Boundless Trail - Section 12 (Printable Map)
TRAIL DIRECTIONS
We’ve created turn-by-turn directions for the entire Boston Boundless Trail, and each trail section guide also includes information about public transit and food connections.
Boston Boundless Trail - Section 1 Directions
Boston Boundless Trail - Section 2 Directions
Boston Boundless Trail - Section 3 Directions
Boston Boundless Trail - Section 4 Directions
Boston Boundless Trail - Section 5 Directions
Boston Boundless Trail - Section 6 Directions
Boston Boundless Trail - Section 7 Directions
Boston Boundless Trail - Section 8 Directions
Boston Boundless Trail - Section 9 Directions
Boston Boundless Trail - Section 10 Directions
Boston Boundless Trail - Section 11 Directions
Boston Boundless Trail - Section 12 Directions
TRAIL CONDITIONS
The City On The Hills Trail is 31.1 miles long with around 1,800 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 5 is the most level section of the trail (but there are still a few hills.)
PUBLIC TRANSIT
You can connect to each section of the City On The Hills Trail by using the MBTA transit system. Below you'll find transit connections to each section trailhead. In the directions for each trail section, there are additional transit connections listed for the "halfway" points near the middle of the trail’s five sections. In other places, you have to go rogue and venture off-trail to reach local buses or trains.
City On The Hills Trail Section 1 trailhead, Millennium Park (West Roxbury)
- Bus lines: 36
City On The Hills Trail Section 2 trailhead, Chestnut Hill Square mall (Chestnut Hill)
- Bus lines: 60
City On The Hills Trail Section 3 trailhead, Washington Street Station (Allston/Brighton)
- Bus lines: 65
- Subway: Green Line at Washington Street Station
City On The Hills Trail Section 4 trailhead, Roxbury Crossing Station (Roxbury)
- Bus lines: 15, 19, 22, 23, 28, 44, 45, 66
- Subway: Orange Line at Roxbury Crossing Station
City On The Hills Trail Sections 5 trailhead, Savin Hill Station (Dorchester)
- Bus lines: 18
- Subway: Red Line at Savin Hill Station
City On The Hills Trail’s end at Castle Island (South Boston)
- Bus lines: 7, 9, 10, 11
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
