Dipsea Generations

Five young Bay Area runners chase glory in America’s oldest trail race while redefining who belongs in the sport.

Trail running is disappointingly homogenous, yet the Bay Area is home to a diverse population and some of the best trails in the US. This film follows five young runners from across the Bay Area as they take on the oldest, and perhaps the most unique, trail race in the US, the iconic Dipsea race. Its unique handicap start makes it ripe for improving access to the sport.

Our documentary celebrates the rich history of this iconic race while using it as a platform to reimagine who belongs in trail running and mountain sports. In the San Francisco Bay Area, one of the most affluent regions in the country, trail running has often mirrored broader disparities in access to outdoor spaces. This film seeks to challenge that legacy by highlighting community leaders, programs, and families working to expand access for youth of all backgrounds. Through their stories, we explore how running can be a vehicle for confidence, self-worth, and a deeper relationship to nature, especially for kids from historically marginalized communities.

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The World Trails Film Festival is a sponsored project of Fractured Atlas, a non-profit arts service organization. Contributions for the charitable purposes of The World Trails Film Festival must be made payable to “Fractured Atlas” only and are tax-deductible to the extent permitted by law.

Dipsea Generations (Trailer)

Five young Bay Area runners chase glory in America’s oldest trail race while redefining who belongs in the sport.
Filmmaker: Paddy O’Leary
Community, Running, Youth