Trail Running calendar near Henrietta 2026-2027

Run a scenic chip timed 5K through Sheldrake Point Winery vineyards overlooking Cayuga Lake on wide grass and packed dirt trails. Enjoy live music, food trucks and a complimentary glass of wine for those 21 and over.

Celebrate July 4 with Finger Lakes 50s, a looped trail race in Finger Lakes National Forest near Hector NY offering 50 miles, 50K and 25K options on mostly single track with rolling climbs. Camp in the forest and enjoy awards and a BBQ at t..

Run under the stars at Dark & Dirty, a night trail race at Batawa Ski Hill on July 11, 2026. Choose 7 km or 14 km over rugged, technical trails with mandatory headlamps, great finish medals and on course aid.

Experience rugged Finger Lakes scenery at the High Tor Trail Marathon in Naples, NY on July 11, 2026, starting and finishing at Naples Community Park. Expect challenging climbs, flowing downhills and two scenic loops for the full marathon.

Experience the scenic Keuka Outlet Trail in Penn Yan on July 18, 2026 with half marathon and 10K options plus virtual entries. Limited to 400 runners, the race wraps up with music and food at the Moose Lodge.

Cancelled: the Webster Trail Runs in Webster, NY have been cancelled. The races featured 10 mile, 3.5 mile and 1 mile kids runs on varied trails through old growth forest, open fields, bridges and single track across three neighboring parks..

Join the Mighty Mosquito Trail Fest July 25-26 at Mendon Ponds for a weekend of trail runs from 5 miles to 100 miles, team relays, camping, night runs and communal meals. Proceeds benefit the Blue Foundation.

Take on the Summer Beast of Burden in Lockport NY with 25, 50 or 100 mile options along the scenic Erie Canal towpath and historic draw bridges. Stocked aid stations keep you fueled and 100 mile finishers can earn a Double Beast Buckle.

Run the rugged Bristol Hills Branch on a 100K point to point ultramarathon through the Finger Lakes, mostly single track with big climbs and scenic views. With a 20 hour cutoff and UTMB and Western States qualifying status, it rewards grit.

Run the Two Hollows Monster Marathon or Half Marathon in Virgil NY on Aug 30, 2026, over scenic hemlock and hardwood trails with rolling single track and a tough climb near the finish. Cupless race so bring your own hydration.

Hit the trails at Ontario Summit Trail Races in scenic Ontario County Park at Gannett Hill, with short and long course options for trail runners of all levels. Enjoy camping, post race food and drinks, giveaways and a friendly community vib..

Join ROCovery's Run Walk X Challenge on Sept 13, 2026 at Mendon Ponds Park in Henrietta, NY to support people in recovery. Run or walk in person or virtually with 5k and 10k options and help a cause that has engaged over 11,000 people.

Take on a rugged 100 km trail ultramarathon around Morgan Hill State Forest, starting and finishing at Spruce Pond in Tully, NY. Scenic single track, big climbs, and a relay option make this a challenging forest adventure.

Take part in a scenic 5K through Sunshine Camp's trails, then celebrate with craft beer, food trucks, music and family fun at the Beer Fest. Proceeds support Rochester Rotary Sunshine Camp for kids and young adults with disabilities.

Join the Boos & Brews 5K in Mendon for a spooky fun trail run with in person and virtual options, a costume contest, and a post race party at the Cottage Hotel. Proceeds benefit David's Refuge to support families of children with special ne..

Many Lite on October 18, 2026 in Letchworth State Park, Castile NY, offers a 20 mile trail run and a 20 mile hike through the Genesee River gorge. Enjoy sweeping overlooks, towering cliffs and autumn foliage on this scenic autumn route.

Hit the trails at the 0 Degree Winter Trail Festival in Pittsford NY on December 12, 2026 for community fundraising and crisp winter racing. Choose 15, 10 or 5 mile routes with tough sections like Hell on Roots and Ski Hill Climb.