The best running trails around Brookline

47runs

3.4

(7)

1,142 people ran here

Running around Brookline is one of the best ways to explore more of this region. To help you discover the most beautiful places to run, we’ve reviewed our full collection of routes around Brookline—and are proud to present the best running trails. Click on any of the routes for more details and browse real tips and photos uploaded by other runners.

Newton & Chestnut Hill loop — Newton	Intermediate 01:20 12.8km
Olmstead Park & Jamaica Pond loop — Brookline	Intermediate 00:54 8.63km
Chestnut Hill Reservoir loop from Englewood Avenue	Intermediate 00:44 7.01km
Jamaica Pond loop from Brookline Hills	Intermediate 00:48 7.65km

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Map data © OpenStreetMap contributors
1
1
Newton & Chestnut Hill loop — Newton
01:20
12.8km
6:16/km
100m
100m
Intermediate
5.0
(1)
39
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Map data © OpenStreetMap contributors
2
2
Olmstead Park & Jamaica Pond loop — Brookline
00:54
8.63km
6:12/km
40m
40m
Intermediate
8
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Map data © OpenStreetMap contributors
3
3
Chestnut Hill Reservoir loop from Englewood Avenue
00:44
7.01km
6:12/km
30m
30m
Intermediate
212
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Map data © OpenStreetMap contributors
4
4
Jamaica Pond loop from Brookline Hills
00:48
7.65km
6:13/km
40m
40m
Intermediate
3.0
(2)
210
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.