The best running trails around Brookline
4.0
(8)
1,536
runners
52
runs
Last updated: October 2, 2025
5.0
(1)
39
runners
1. Newton & Chestnut Hill loop — Newton
12.8km
01:20
100m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
8
runners
2. Olmstead Park & Jamaica Pond loop — Brookline
8.63km
00:54
40m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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5.0
(2)
188
runners
3. Running loop from Amory Street Station
5.53km
00:35
10m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
187
runners
4. Hatch Memorial Shell loop from Babcock Street
8.42km
00:53
20m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
83
runners
5. Jamaica Pond – Olmsted Park loop from Brookline Village
17.3km
01:52
140m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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