The best running trails around Woodside
4.5
(24)
2,651
runners
207
runs
Last updated: October 26, 2025
1
runners
1. Tripp Road via Woodside Road loop — Woodside
5.29km
00:36
30m
30m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
59
runners
2. Running loop from Portola Valley
23.2km
03:07
840m
840m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Sign up for free
35
runners
3. Bear Gulch Trail (Meadow) loop from Woodside
16.0km
02:13
570m
570m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
runners
4. Running loop from Woodside
5.10km
00:43
200m
190m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
7
runners
5. Borel Hill loop from Portola Valley
28.5km
03:44
770m
770m
Expert run. Very good fitness required. Sure-footedness, sturdy shoes and alpine experience required.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Other adventures around Woodside
Most popular attractions around Woodside
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