Penn Yan
Trail Running Calendar near Penn Yan 2026-2027
Explore the top trail runs near Penn Yan 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.
August 2026
A point to point 100K trail ultramarathon in Naples NY on August 22 2026 featuring nearly all single track terrain, 11 aid stations, a 20 hour cutoff, shuttle and free camping.
September 2026
Multi-day timed ultras at Shortsville Reindeer Farm on a one mile grass and trail loop. Multiple timed options, an on-course aid barn, and belt buckles for finishers who complete 100 loops; proceeds support ROCovery Fitness.
October 2026
Trail races near Canadice and Hemlock lakes offering marathon, 15K and a point-to-point 5K with technical single-track sections and two major climbs.
Hopson Trail Runs in Honeoye offers scenic fall trail routes of 5K and 9K through WoodsEdge Retreat and Sandy Bottom Park. The event supports Embrace Your Sisters and includes a post race gathering at Birdhouse Brewery with music and a complimentary..
November 2026
Run or walk as many loops as you choose during this 6 hour event on the Manchester Gateway Trail. This dog friendly race features a scenic 2.3 mile course and benefits the local dog park through a dedicated raffle.
January 2027
Winter trail race on Jan 2, 2027 at Harriet Hollister with an approximately 10k loop, no on-course aid, and a post-race gathering in Honeoye.
March 2027
June 2027
A free, community hill-loop challenge in Naples supporting the Naples Trail Collective, where participants record GPS loop times and reconvene at Engine 14 Brewery to compare results. Multiple named climbs cover local trails and cultural sites.