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Trail Running Calendar near Cupertino 2026-2027

Monthly updates for Cupertino

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

Explore the top trail runs near Cupertino for 2026-2027! We've gathered 48 exciting races in the area. Check out our detailed list below to find your next local race.

November 2026
Nov
7
Sa

Rancho Hills Trail Run - Fall

Trail Run 5 km 10 km ... Marathon 50 km
Nov
14
Sa

Zombierunner Quarry Lakes

Trail Run 2 mi 5 km 10 km 13 mi
Nov
14
Sa

Go Wild Santa Cruz 4 Hr

Trail Run
Nov
26
Th

Zoom Turkey Trot

Trail Run 2 mi 5 km 10 km 13 mi
Nov
26
Th

The Animal Run Tofurkey Trot

Trail Run Walk 5 km
Nov
28
Sa

Quarry Turkey Half Marathon

Trail Run 5 km 10 km 13 mi
December 2026
Dec
5
Sa

Calero Trail Run - Winter

Trail Run 5 km 10 km ... 26 mi 50 km
Dec
12
Sa

Summit Rock Half Marathon

Trail Run 5 km 10 km Half Marathon
Dec
19
Sa

Woodside Ramble

Trail Run 6 mi 13 mi 23 mi 31 mi
Dec
31
Th

Brazen New Year's Eve

Trail Run 5 km 10 km Half Marathon
January 2027
Jan
1
Fr

Brazen New Year's Day

Trail Run 5 km 10 km Half Marathon
Jan
2
Sa

Hacienda Hills Trail Run - Winter

Trail Run 5 km 10 km ... Marathon 50 km
Jan
17
Su

Crystal Springs (Winter) Trail Run

Trail Run 8 km Half Marathon ... Marathon 50 km
Jan
17
Su

Crystal Springs Trail Run

Trail Run 5 mi 13 mi ... 26 mi 50 km
Jan
30
Sa

Coyote Hills Run

Trail Run Walk 5 km 10 km Half Marathon
February 2027
Feb
6
Sa

Mt. Umunhum Trail Conquest - Winter

Trail Run 5 km 7 mi ... 26 mi 50 km
Feb
13
Sa

Bay Breeze - San Leandro

Trail Run 5 km 10 km 13 mi
Feb
27
Sa

Sanborn Trail Challenge

Trail Run 4 mi 8 mi 13 mi
March 2027
Mar
6
Sa

Race to the Top of Mt. Umunhum

Trail Run 13 mi
Mar
20
Sa

South Hills Single Track Trail Run - Spring

Trail Run 5 km 10 km ... Marathon 50 km
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