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Trail Running Calendar near San Jose 2026-2027

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Explore the top trail runs near San Jose for 2026-2027! We've gathered 47 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Aug
8
Sa

Mount Madonna Challenge

Trail Run 5 km 10 km 13 mi
A trail running event on Aug. 8, 2026 in Gilroy, California through redwood groves and peak viewpoints. Distances include a 5K, 10K and half marathon with significant elevation gain, and proceeds support youth scholarships.
Aug
15
Sa

Almaden Hills Trail Run - Summer

Trail Run 5 km 10 km ... Marathon 50 km
Trail races on hilly mixed dirt and single track at Almaden Quicksilver Park with distances from 5K to 50K, aid stations, drop bag service for longer races, and mandatory course markings and cutoffs.
Aug
16
Su

Race Thru the Redwoods

Trail Run Walk 10 km
A trail and road race through Henry Cowell Redwoods with a 10K and a 1-mile kids race starting and finishing at Roaring Camp Railroads in Felton.
Aug
22
Sa

Santa Cruz Trail Run

Trail Run 6 mi 14 mi 30 km
Trail races of 10K, half marathon and 30K in Henry Cowell Redwoods State Park featuring redwood single-track, a sandy ridge, river crossings, and cupless aid stations.
Aug
23
Su

Santa Cruz Track Club Cross Country Challenge

Trail Run 4 mi
A two loop 4.15 mile cross country race on the fire roads of the UC Santa Cruz campus, starting and finishing at the meadow above the fire station and included in the Pacific Association USATF Grand Prix series.
Aug
29
Sa

Crystal Springs Trail Run

Trail Run 2 mi 6 mi ... 26 mi 31 mi
Trail races at Huddart Park, King's Mountain and Bear Gulch offer measured distances from a 50 yard kids dash to a 50K, with fees listed per distance and registration opening November 11, 2025.
September 2026
Sep
12
Sa

Stevens Creek Striders Reservoir Run

Trail Run Walk 3 mi 11 km 13 mi
A trail race at Stevens Creek County Park in Cupertino offering a Half Marathon, 11K, and a charity 2.5-mile Lollipop Loop with aid stations and post-race barbecue.
Sep
12
Sa

Beer City Half Bishop Ranch

Road Race Trail Run Walk 5 km 10 km 13 mi
Run through Bishop Ranch and San Ramon in this diverse racing event. Choose between a half marathon, 10k, 5k, or beer mile before enjoying unlimited tastings with your finisher medal.
Sep
12
Sa

South Hills Single Track Trail Run - Summer

Trail Run 5 km 10 km ... Marathon 50 km
A trail running event at Calero County Park offering distances from a kids run to a 50K across single-track and dirt roads, with named aid stations, drop bag support, bib color assignments, and time limits for longer races.
Sep
19
Sa

Rocky Ridge

Trail Run Walk 3 mi 6 mi 14 mi
Trail-based half marathon plus 5K and 10K with hills and scenic views in San Ramon on September 19, 2026; virtual entries available.
Sep
26
Sa

Dick Collins Firetrails

Trail Run Marathon 50 mi 100 km
Trail event in Castro Valley featuring a 100k, 50 mile, and marathon with UTMB index status and firm time limits due to park permits.
Sep
26
Sa

Belmont Water Dog Run

Road Race Trail Run Walk 5 km 10 km
Community-supported Belmont Water Dog Run in Belmont, CA features 5K, 10K, kids' mile, a pet-friendly Fido Mile, and a virtual option on September 26, 2026.
Sep
27
Su

Spartan Trail - San Jose Trail Challenge

Trail Run 10 km Half Marathon 50 km
Trail running in shaded redwood forest at Sanborn County Park on September 27 2026, with 10K, half marathon and 50K options; steep singletrack, shuttle parking, chip timing and specific mandatory gear for the 50K.
October 2026
Oct
4
Su

Run by The Sea

Trail Run 4 km 12 km Half Marathon
Run by the Sea at Wilder Ranch State Park on October 4, 2026 offers a Half Marathon, 12K and 4K run/walk along mostly flat packed dirt trails with coastal bluff and Monterey Bay views. Organized by the Santa Cruz Track Club; proceeds benefit local gr..
Oct
10
Sa

Mt. Umunhum Trail Conquest-Fall

Trail Run 5 km 7 mi ... 26 mi 50 km
Oct
17
Sa

Quicksilver Trail Challenge

Trail Run 10 km 13 mi
Trail races at Almaden Quicksilver County Park include a half marathon, 10K and a kids one mile fun run with course aid stations and volunteer support.
Oct
31
Sa

Zombierunner Halloween

Trail Run 2 mi 5 km ... 13 mi 26 mi
Celebrate Halloween with a trail race through San Jose Hellyer County Park. Choose from distances including 5K 10K Half Marathon and Marathon with costume prizes and certified courses.
Oct
31
Sa

Almaden Hills Trail Run - Fall

Trail Run 5 km 10 km ... Marathon 50 km
Trail races in Almaden Quicksilver Park from 5K to 50K over hilly dirt roads and single-track, with two staffed aid stations, drop-bag service for longer distances, and a finisher medal for all participants.
November 2026
Nov
7
Sa

Mermaid Trail Run - Woodside

Trail Run Walk 3 mi 6 mi 9 mi Half Marathon
Trail trail event at Huddart Park in Woodside offering distances from a 1 mile kids dash to a Sirena 6 hour individual and relay challenge.
Nov
7
Sa

Lake Chabot Trail Run

Trail Run 2 mi 3 mi ... 26 mi 50 km
Experience a scenic trail run around the Lake Chabot reservoir and hills. With distances from a 50 yard kids dash to a 50K ultramarathon there is an option for everyone at this Castro Valley event.
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