Middletown
Trail Running Calendar near Middletown 2026-2027
Explore the top trail runs near Middletown for 2026-2027! We've gathered 10 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
November 2026
A 6.45 mile trail race in Annadel State Park held as the 40th annual event with staggered starts, awards for the top 13, and limited registration to 100 runners.
Trail races at Brassfield Estate Winery in High Valley AVA offering 5K, 10K and 10 mile courses with vineyard views, a finish line celebration, and wine for 21 and over.
An uphill 3.1 mile trail race in Kelseyville on November 14, 2026, running from the base of Mt. Konocti to Wright Peak with summit awards and post-race lunch.
March 2027
Trail event in Middletown CA on March 7, 2027 offering Half Marathon, 10K and 5K on a scenic looped course with camping options and post race food.
Trail races at Bothe-Napa Valley State Park offering marathon, half marathon, 10K and 5K on single track trails with stream crossings and limited entries.
April 2027
Three Lake Sonoma trail races in early April 2027 including a Western States qualifying 100k, a 50k with a bridge crossing, and a women only half marathon.
Trail running event on April 17, 2027 with a hilly half marathon, 10K and 5K, over 1500 ft of ascent and a cup-free policy.
Trail races at Jack London State Historic Park on April 17, 2027 offering Half Marathon, 5.5 mile and 5K courses through vineyard views and Sonoma Mountain hills.
May 2027
A timed half marathon on May 8, 2027, from Quintessa Winery to Yountville with exclusive vineyard access, festive aid stations, and a finish-line Wine Village.