Trail Running calendar near Wading River 2025-2026

Run The Farm is a scenic 5 mile trail race at Muscoot Farm with fun kids races for younger runners. Finishers receive Farm Bucks to spend at the Muscoot farmers market and event shirts are available while sizes last.

Take on the scenic Mine Hill Half Marathon on May 25 in Roxbury, CT, starting and finishing at Mine Hill Distillery. Enjoy a challenging climb, a fast downhill second half, a finisher medal and post race food and drinks.

Challenge yourself at Mohawk Mountain in early June 2026 with timed endurance events from 12 hour to 84 hour and distances up to 152 miles. Race solo or with Trail Buddy or Trail Family teams, tackle night sections and enjoy base support an..

Run or ride scenic farm trails at Norbrook Farm Brewery in Colebrook CT, with options from a 5K and 10K to a 4 hour trail challenge, duathlon and competitive mountain bike races. Finishers get custom medals and entrants 21 plus receive a fr..

Take on a scenic 15.7 mile trail run on the Nipmuck Trail in Mansfield CT, following the Fenton River through woods, fields and small bridge crossings. Organized by the Shenipsit Striders, proceeds support local trail stewardship.

Run the Centurion Ultra at Roosevelt Forest in Stratford CT, a timed 100 mile trail test through classic New England terrain with a 33 hour cutoff. Limited to 50 runners, buckles await 100 mile finishers.

Join Pinky's Rock n Rolla, a 4 mile trail race through Forest Park's scenic trails in Richmond Hill, NY. Enjoy rugged natural terrain, medals for all finishers, prizes for top runners, and proceeds benefiting Puppy Kitty NYCity.

The The Squatchy Surprise will take place in West Orange on Saturday 25 July 2026. You can run between 3 and 12 kilometers.

Take on the Interstate 17 Trail Run, a 17 mile looped trail race at State Line Lookout with serious elevation and rugged technical terrain. Rocky scrambles, waterfalls and required loop check ins make this a scenic tough challenge.

Join the Stonington Cross Country 5K in Pawcatuck CT on Wednesday August 12 2026 for a free community race that blends one track loop, quiet campus roads and scenic trails. A children's 1/2 mile for ages 10 and under also finishes on the sc..

Tackle a scenic 5K through Oswegatchie Hills Nature Preserve, winding past Clark Pond on root and rock strewn trails; hikers welcome. This fourth annual run benefits preserve maintenance and finishes with local pub awards and camaraderie.

Tackle rugged single track, steep climbs and scenic summit views at Macedonia Brook State Park with 12K, 25K and 50K options. The 25K is part of the Blue Blazed Trail Running Series for a true New England trail challenge.

Experience day and night running at the Pawling 24 Hour Trail Running Festival in Lakeside Park, with looped 3, 6, 12 and 24 hour timed races, music and on course aid. All finishers get medals and crews can set up on the festival field.

Hit the newly restored Moosup Valley State Park Trail on Sunday, September 27 for scenic 5K, 10K and a kids fun run on all trail terrain. Post race food and gear, leashed dogs welcome, and proceeds support the Rotary Club of Plainfield.

Take on the Iron Hike Fall Olympus Mons Ultra Trail Marathon Relay in Cornwall Connecticut, a team endurance challenge across Mohawk Mountain covering 152 plus miles with massive elevation gain. Run, hike or walk the course within an 84 hou..

Take on a 24 hour trail challenge at Mohawk Mountain with a 28 plus mile course and huge elevation gain that rewards grit and strategy. Run, hike, or walk solo or as a relay with veteran owned IronHike Endurance Productions.

Test your limits in the Forbidden Forest 30 hour ultra at Roosevelt Forest in Stratford CT, covering as many miles as you can on a rugged 2.23 mile trail loop. Options span marathon to 100 miles with small field support.

Run the Mohawk Mountain Race at Mohawk Ski Area in Connecticut on Oct 12 with distances from 5K to marathon and rolling trails through Mohawk State Forest. Expect big climbs, rugged singletrack, aid stations and a finisher medal.

The Big Bear SquaTCh South will take place in Tuxedo Park on Sunday 18 October 2026. You can run between 10 and 13 miles.

Run 13.1 miles on forest trails at the Storybook Half Marathon in Roosevelt Forest, Stratford CT, completing eight scenic loops of single and doubletrack. Wear a costume, enjoy post race perks, and donate children's books to Books4Everyone.