Cycling & running events in San Jose, 2026

South Bay Training Ground

Running: Locals use the Guadalupe River Trail, Stevens Creek Trail, and San Tomas Aquino Creek Trail for steady weekday miles. The Guadalupe River Trail gives you 5 miles of nice flat warmup. Sunnyvale runners keep John W Christian Greenbelt and the Bay trail in the rotation, and pond A4 gives a simple 3 mile loop. Santa Clara-San Jose Running Group meets each Saturday at 9:00 AM and runs down The Alameda toward downtown San Jose. SUNNYVALE RUN CLUB meets Wednesday at Sports Basement Sunnyvale at 6:00 PM. San Jose Half Marathon & 8K, ZombieRunner Halloween, Zoom Turkey Trot, Beer City Half San Jose, and Quicksilver 100K and 50K anchor the calendar.

Cycling: Cyclists build base miles on Coyote Creek Trail, Los Gatos Creek Trail, Guadalupe River Trail, and Stevens Creek Trail. The route covers 3 km with 1,173 m of climbing. Mt. Hamilton is the big test, and the Mount Hamilton Challenge climbs to Lick Observatory atop 4,209 foot Mt. Hamilton. ACTC, FFBC, Alto Velo Racing Club, LGBRC, San Jose Bicycle Club, Skyline Bicycle Club, and SVMTB keep the group rides serious. Sierra Vista Open Space, Santa Teresa County Park, Jim Donnelly Trail, and Baylands Gravel handle the dirt, singletrack, fireroads, and cyclocross legs.

Season: April feels busy because Pedalera Bicycle Club hosts the Mount Hamilton Challenge, Team MMUZ hosts Gravel Grinding, and FFBC runs the Progressive Ride Series from January through April. Summer gives cyclists Skyline Bicycle Club Wednesday Night Rides from April through September, and Shiny Side Up lands at San Jose’s History Park on the last Sunday in July. Runners keep using shaded starts, creek trails, and coffee-shop loops when Z2 needs to stay honest. Winter changes the route choice more than the mindset, and the San Tomas Aquino Creek Trail is less prone to flooding during winter. Locals still get intervals, base miles, gravel, and trail days done year round.