Trail Running Calendar New York 2025-2026

Celebrate spring at the Brooklyn Cider House Spiked Apple 5K on April 19 in New Paltz, a scenic two lap run through vineyards and orchards. Enjoy a cider pour, fresh donut, finisher medal and commemorative shirt.

Squatchywaska Mountainfest in Ellenville NY on April 25, 2026 serves up technical singletrack on the Shawangunk Ridge with 25K and 10 mile options, big climbs and sweeping Catskill views. This rugged trail event also supports protection of..

Enjoy a spring 10k trail race in Cross River, NY on April 26, 2026, winding through scenic park trails. Entry is by lottery with registration opening January 2, 2026, perfect for trail runners seeking a well organized challenge.

Join the AdironDUCK 5K in Croghan for a fun untimed trail run, walk or bike ride with a pancake breakfast included. Casual and family friendly, helmets required for cyclists and shirts may be available on race day.

Join the VCP50k in the Bronx on May 2, 2026. It starts with a flat lap then ten cross country loops with rocks, roots and some climbing. Aid stations, drop bags, medal, singlet, hot meal and beer await finishers.

DENFIT ULTRA at Buffalo Ski Center is a 10 km ski slope loop with 50k or 100k options, offering big elevation and possible snow. Parts are unlit so headlamps are required and finishers earn medals and custom spears.

Run the 5th annual Black River Trail in Watertown NY along a smooth, flat paved course with scenic river views. Choose 5K to 15K plus ruck and virtual entries, enjoy a shirt and medal, and celebrate while supporting local transit volunteers..

Join A Run to Remember on May 2 in Red Hook and run or walk scenic farm trails through meadows, orchards, and woods at Greig Farm. Honor loved ones, celebrate community spirit, and vie for cash prizes in the 5K and 10K races.

Take on Breakneck Point on May 3, 2026 in Beacon, NY with a rugged half or full ultramarathon featuring huge elevation and technical single track. Expect steep exposed climbs, aid stations, and a finisher shirt and memento.

Join the 19th Annual Medved Madness Trail Races on May 3, 2026 at Mendon Ponds Park in Honeoye Falls NY for scenic trail running. Choose about 13 mile or 5 mile courses or a kids run, then relax with a post race barbecue and a technical shi..

Take on Greek Peak UltraTrax in Cortland NY on May 9, 2026, with 1 to 4 loops of a rugged 7 mile course offering about 1,480 ft of climb per loop. Enjoy shaded single track, sweeping Finger Lakes foothill views, timed support, aid stations,..

Run Letchworth State Park's dramatic gorge at the Sehgahunda weekend, with distances from 5K and relays to a two day 72K. Cup free aid stations, post race food, event shirts and unique finisher items await.

Run a scenic 5 mile trail at Muscoot Farm with kids races for ages 2 to 12 and a family friendly vibe. Finish with Farm Bucks to spend at the Muscoot Farmers Market and optional shirts available by advance order.

Sand to Serengeti offers scenic trail runs at Green Lakes State Park, starting on the sandy beach and climbing to the Serengeti high section. Run 10 miles or 3 miles and support Safe Space Organization's peer to peer mental health work.

Run among the waterfalls at Letchworth State Park on May 17 with 5K, 10K, or 15K routes starting and finishing at the Parade Grounds. Enjoy hilly, scenic out and back courses with sweeping Genesee River views and post race refreshments.

Enjoy a scenic 5k at Ledge Rock Hill Winery in Lake George with a cross country style course and options to volunteer and run. Finishers get a medal that doubles as a wine stopper, a shirt and a wine pour.

Run Like The Wind 5K in Ellenville offers a scenic course along the Shawangunk Mountains and the newly resurfaced Rail Trail. Finish at Aroma Thyme Bistro for garden drinks and food while supporting local food pantries and youth scholarship..

Recharge your trail season at Spring Training Camp in Oliverea NY, May 22 to 24, 2026. Small group guided coaching blends mountain trail skills, long climbs and technical terrain with mental performance work to sharpen your race readiness.

Run a scenic 5K through Blydenburgh County Park in Smithtown on May 23, 2026, with a free Kiddie Dash for kids. Join in person or virtually, enjoy trails and post race refreshments while supporting the Never Stop Running Foundation.

Run Cayuga Trails on May 30, 2026, through Ithaca gorges, waterfalls and historic stone stairs with wild singletrack underfoot. Choose a 50 mile or 50K challenge for a scenic, rugged ultramarathon experience.