Middletown
Trail Running Calendar near Middletown 2026-2027
Explore the top trail runs near Middletown for 2026-2027! We've gathered 11 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Trail races at Lake Sonoma on October 17–18 2026 offering 100, 50, marathon, half and relay options with significant elevation and staffed aid stations.
November 2026
The 40th annual Annadel Loop is a 6.45 mile trail race in Annadel State Park with staggered starts, awards for the top 13, a limited field, and published member and non member fees.
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 with camping, awards, and proceeds benefiting trail development and charity.
Trail marathon, half marathon, 10K and 5K on the single track at Bothe Napa Valley State Park on March 20, 2027 with a 300 runner limit.
April 2027
A spring Lake Sonoma trail weekend featuring a Western States qualifying 100K, a 50K with a bridge crossing, and a women only Trail Sisters 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 runs at Jack London State Historic Park offering Half Marathon, 5.5 Mile and 5K on marked courses with aid stations, limited parking, and a no headphones policy.
May 2027
Scenic timed half marathon through Napa vineyards from Quintessa Winery to Yountville, featuring winery aid stations, a Finish Line Wine Village with tastings, shuttle service and a finisher medal.