Hunter S. Thompson Fear & Loathing

Midtown Terrace, United States • 7 Dec 2025

The Hunter S. Thompson Fear & Loathing is a unique, no-fee urban ultra running event held annually in San Francisco, CA, since 1985. Participants can choose between a 50K or 50-mile single-loop course that starts and finishes at Twin Peaks, offering stunning city vistas.

The route covers iconic tourist spots mostly on city streets, with the 50-mile distance including some parallel trail options. Runners face a total elevation gain and loss of 3,600 feet, with a high point at 847 feet. The event embraces a "no awards, no aid, no wimps" philosophy but provides several informal aid stations.

It encourages navigation skills and urban adventure, making it a challenging and scenic race through San Francisco. Visit the organization's website for the most recent information.

Race information

50 mi
3600 m+
50m
50 km
3600 m+
50k
Visit the organization's website for the most recent information.
Trail runs nearby

The Woodmonster Trail Race is a challenging 10-mile trail run held in Oakland, California, starting and finishing at the Chabot Space & Science Center. The course features a mix of hills and single-track trails, including the notorious Woodmonster climb, known for its steep and demanding ascent. Run..

The Rock the Loch Half Marathon is a scenic trail running event held at Lake Chabot Regional Park in Castro Valley, California. Scheduled for late June 2025, it offers live and virtual participation options across three distances: 5K, 10K, and half marathon. The 5K is fully paved, ideal for beginner..

The Bay 2 Bankers 10K is a unique running event held in San Francisco, starting near the iconic Ferry Building. Now in its 13th year, the race features a mystery theme celebrating the classic vibes of the city. Participants run through various historic neighborhoods, navigating from checkpoint to ch..

The Dirty Dozen Run is an annual trail running event held at Point Pinole Regional Shoreline in Richmond, California. It features 12-hour, 6-hour, and 3-hour endurance races on a scenic 3.37-mile loop composed mostly of dirt fire trails. The course offers expansive shoreline views, including multipl..

The Muir Woods Mountain Challenge, held at Mt. Tamalpais State Park near Stinson Beach, California, offers trail runs of 10K, half marathon, and 30K distances. The course features a challenging 2,000-foot climb early on, scenic ridge-line views of Stinson Beach and the Pacific Ocean, and technical s..

The Rodeo Valley Trail Run, held in the scenic Marin Headlands near Sausalito, CA, offers trail races of 8K, Half Marathon, 30K, and 50K distances. Starting near historic Fort Cronkhite and Rodeo Beach, the course features challenging steep climbs and descents along coastal trails with stunning view..