The best running trails around Winchester
1
runners
3
runs
Last updated: October 25, 2025
1
runners
1. Kilburn Pond loop — Pisgah State Forest
4.85km
00:32
50m
50m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
2. Fort Hill Recreational Trail — Cheshire County
9.74km
01:00
30m
30m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Sign up for free
3. Mount Pisgah via Parker Trail — Pisgah State Forest
8.95km
01:11
240m
240m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4. Pisgah State Forest loop via the Lily Pond Trail
7.57km
01:00
200m
200m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5. Hubbard Hill loop via the Hubbard Hill Trail — Pisgah State Forest
10.3km
01:21
270m
270m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Most popular routes around Winchester
Most popular attractions around Winchester
Get inspired with the komoot mobile app
Explore more
Browse the best Running Trails & Routes in other regions.
Get ready to conquer new peaks
Sign up for Free