Trail Running calendar near San Luis Obispo 2026-2027

A chip timed 5k at CASS Winery in Paso Robles on April 19 2026 that runs through the winery grounds and includes race swag, a wine pour for eligible participants, virtual options, and age group awards.

Born To Run Ultra Marathon Extravaganza takes place in Los Olivos, CA on May 16, 2026 and offers distances from 10 miles up to 100 miles plus three day and four day formats. Registration opens December 1, 2025.

Run a scenic mixed terrain 5K, 10K or Kids Mile over rolling hills at Thousand Hills Ranch in Pismo Beach. Stay for a family friendly festival with live music, local vendors, and fundraising for CCAF and 17 Strong.

A two day trail running and camp event in Bradley CA on September 18 and 19, 2026. It features 48 hour and 24 hour timed formats plus 20 km and 10 km trail races.

Trail running at Smith Ranch near Bradley, CA on September 19, 2026. Options include 5km, 10km, 20km and 24/48 hour loop formats on 100% dirt single track with on-site camping and nightly bonfires.

The Rancho Ramble Trail Run will take place in Santa Margarita on Sunday 1 November 2026. You can run between 10 and 50 kilometers.

Island View Endurance Run returns to Goleta, California on December 4 and 5, 2026, with distances from 12K to 100 miles. Enjoy scenic coastal trails and multi day endurance challenges; registration opens April 1, 2026.

La Cuesta Ranch Trail Run in San Luis Obispo on January 23, 2027 offers 10 km, 20 km and 30 km trail races. Race day photos are posted and the hashtag #LaCuestaRanchTrailRun2026 is used for social posts.