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Trail Running Calendar near Woodside 2026-2027

Monthly updates for Woodside

Get new running races (and updates) in your inbox every month.

Explore the top trail runs near Woodside for 2026-2027! We've gathered 39 exciting races in the area. Check out our detailed list below to find your next local race.

June 2026
Jun
7
Su

Lake Chabot Trail Challenge

Trail Run 3 mi 13 mi
Jun
13
Sa

Bay Area 100

Trail Run 100 mi
Jun
26-29
Fr - Mo

The Rock The Loch Half Marathon

Trail Run 5 km 10 km Half Marathon
July 2026
Jul
4
Sa

Bay 2 Bankers 10K

Trail Run 5 km 10 km
August 2026
Aug
2
Su

Skyline 50k Endurance Run

Trail Run 50 km
Aug
15
Sa

Redwood (Summer) Trail Run

Trail Run 5 mi 13 mi ... Marathon 50 km
Aug
22
Sa

Santa Cruz Trail Run

Trail Run 10 km Half Marathon 30 km
Aug
30
Su

Crystal Springs Trail Run

Trail Run 8 km Half Marathon ... Marathon 50 km
September 2026
Sep
26
Sa

Dick Collins Firetrails

Trail Run 26 mi 50 mi 100 km
Sep
27
Su

Spartan Trail - San Jose Trail Challenge

Trail Run 10 km Half Marathon 50 km
October 2026
Oct
10
Sa

Ruth Anderson Memorial Endurance Run

Trail Run 50 km 50 mi 100 km
Oct
31
Sa

Zombierunner Halloween

Trail Run 5 km 10 km Half Marathon Marathon
November 2026
Nov
1
Su

Oakland Tech 5km Fundraiser Race

Trail Run 5 km
Nov
7
Sa

Mermaid Trail Run - Woodside

Trail Run 3 mi 6 mi ... 13 mi 6 hr
Nov
7
Sa

Lake Chabot Trail Run

Trail Run 8 km Half Marathon ... Marathon 50 km
Nov
26
Th

Zoom Turkey Trot

Trail Run 5 km 10 km Half Marathon
December 2026
Dec
5
Sa

Zombierunner Quarry Lakes

Trail Run 5 km 10 km Half Marathon
Dec
6
Su

The Krampus Cross Country

Trail Run 5 km 10 km 9 mi
Dec
6
Su

Hunter S. Thompson Fear & Loathing

Trail Run 50 km 50 mi