Progressive Trail Ride

Woodside Day of the Horse Progressive Trail Ride on Saturday October 10, 2026. Join us for the ride and party: Trail Ride 11am-2pm, After Party 1:30pm-4:30pm. Historically, participants from all over California enjoy this legendary trail ride that gives riders a glimpse of rural America right in the heart of Silicon Valley. The official route is on the Woodside Town Trails and ride stops include both public and private horse-friendly locations, concentrating in the areas near central Woodside with a trail loop at the Horse Park at Woodside as well. Participants must bring their own horse or equid, pre-register, sign a liability release, and pay a fee per rider. Lunch and a day stall for your horse are included in the registration fee. The after party includes a polo tournament, demonstrations, refreshments at the VIP Tent, buffet-style lunch, WHOA Foundation Grant Winner displays, sponsoring exhibitors, coffee cart, mocktails, swag sales, silent auction, and announcements of group challenge and costume contest winners.