Trail Running calendar near Pittsford 2026-2027

Cabin Fever Trail Races in Webster Park on February 22, 2026 offers approximately 5 mile and 10 mile trail courses through pine forest; entries include a long sleeve shirt guarantee for early registrants and post race food.

Run or walk a chip timed 5K through scenic vineyards and orchards at Three Brothers Wineries and Estates. Enjoy a cider donut, shirt and a finisher medal that doubles as a bottle opener, with family friendly and virtual options.

Run a scenic 5K through trails and vineyards at Spring Lake Winery in Lockport on April 4, 2026. Enjoy finish line snacks, a keepsake wine glass, and post race food and drinks with live music and festivities.

Timed six hour event in Rochester, NY on April 4, 2026 with two three hour legs. Parking is at Durand Eastman Park on Lakeshore Blvd and registration closes April 3 at 11:59 PM ET.

Trail races at Green Lakes State Park in Fayetteville, NY offering 50km, 20 Miler, and 10 Miler on an approximately 10 mile loop with varied terrain and about 1,300 feet of elevation gain.

A technical *20K* trail run through Hi Tor Wildlife Management Area near Naples, NY, with steep elevation changes, varied terrain and wildlife encounters; entry is limited to 200 runners and a clear refund schedule applies.

The DENFIT ULTRA launches in Buffalo with a midnight start on the slopes of Colden's ski center. Runners tackle a 10k loop course in the dark, facing significant elevation and natural terrain over 50k or 100k. A basecamp tent provides suppo..

Medved Madness Trail Races at Mendon Ponds Park features a roughly 13-mile long course, a 5-mile short course, and a free Kids K, with courses set the day of the event and a post-race barbecue.

Forest loop event at Greek Peak near Cortland, NY on May 9, 2026 offering 7, 14, 21 and 28 mile options. Walk or carry 10, 20 or 35 lb and finish within 10 hours to earn patches and medals.

Trail run of 8 km at Goodrich-Loomis Conservation Area as part of the Happy Hour Friday Night Series. The course includes hills, rocks, roots and mossy log bridges; the event is cupless with water at the start and finish.

A two-day race weekend at Letchworth State Park featuring a 26.3-mile trail marathon with relay options, three out-and-back falls races, and a 72 km challenge, with aid stations, event shirts, and finisher medals for each race.

Trail running at Green Lakes State Park with 10 mile and 3 mile routes starting and finishing at the park beach; water aid stations and race day packet pick-up available. The 10 mile awards include a finisher medal and cash prizes for top f..

Three out and back distances set at Letchworth State Park on seasonal gravel and broken asphalt with scenic Genesee River views. Aid stations, event shirts, post race food and new finisher medals are provided.

A trail ultramarathon near Ithaca, NY featuring 50 mile and 50K courses through singletrack, gorges, waterfalls and stone stairs, with aid stations, drop bag support, limited field size, and proceeds supporting local trail organizations.

Trail races at Robert H. Treman State Park near Ithaca NY offering a half marathon, a 6.66 mile race and a 5K. Courses run on the Rim Trail, through Lucifer Falls gorge and on Finger Lakes Trail singletrack.

Trail races at RMSC Cumming Nature Center in Naples NY on June 6, 2026 with 25k, 10k and a 3k fun run. The 25k is a single loop through nature center and neighboring wildlife lands with on course aid and a cup free policy.

The RHSC's Super Hear-O 5K will take place in Rochester on Sunday 7 June 2026. You can run 5 kilometers.

An evening trail run at Mendon Ponds Park on June 12, 2026 with 4‑mile and 8‑mile options on a marked 4‑mile loop. Off‑road course, carry your own fluids, timing and results provided, and awards for the 8‑mile race.

A two day multisport weekend at Green Lakes State Park featuring sprint triathlon, aquabike, duathlon, aqua run, relay, an 8K trail race, and a kids beach fun run, with proceeds supporting YMCA community programs.

A looped trail event at Batawa Ski Hill featuring a roughly 7 km+ loop and 2, 4 or 6 hour options. The course is marked, cup free and includes an aid station with water and Tailwind.