The best running trails around Winchester
1
runners
3
runs
Last updated: September 25, 2025
1
runners
1. Kilburn Pond loop — Pisgah State Forest
4.85km
00:32
50m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
Easy
2. Fort Hill Recreational Trail — Cheshire County
9.74km
01:00
30m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Intermediate
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3. Mount Pisgah via Parker Trail — Pisgah State Forest
8.95km
01:11
240m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Intermediate
4. Pisgah State Forest loop via the Lily Pond Trail
7.57km
01:00
200m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Intermediate
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Intermediate
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