The best running trails around Portland
87
runners
22
runs
Last updated: October 27, 2025
5
runners
1. Pistol Creek Trail loop — Berlin, Connecticut
3.75km
00:23
20m
20m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
2. Portland Reservoir loop — Meshomasic State Forest
4.72km
00:34
50m
50m
Intermediate run. Great for any fitness level. Mostly accessible paths. Some sure footedness required.
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21
runners
3. Cranberry Bog – Gateway Preserve loop from East Hampton
25.4km
03:04
220m
220m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
10
runners
4. Running loop from Middletown
4.52km
00:29
30m
30m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
4
runners
5. Running loop from Middlefield
3.51km
00:26
50m
50m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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