Trail Running calendar near Milford 2025-2026

Run the Mine Hill half marathon on 24 May 2026 in Roxbury Connecticut, starting and finishing at Mine Hill Distillery. Enjoy rolling country roads with sweeping farm views, then celebrate at the distillery after party.

IronHike Spring 26 at Mohawk Mountain CT in June offers endurance routes from 15 to 152 miles for solo runners, teams and families in a flexible relay format. Enjoy basecamp camping, support stations and finisher gear.

Join the Run in the Park 5K at Eisenhower Park in Milford on June 7 to support the Milford Rotary and the Beth El Center. Enjoy a scenic, mostly flat trail loop welcoming runners, walkers, hikers, families, dogs, and teams.

Run the scenic 15.7 mile Nipmuck South Trail at Mansfield Hollow State Park, following the Nipmuck Trail along the Fenton River through woods, fields and a climb to a cliff. Proceeds benefit Connecticut trail stewardship groups and the Blue..

Run Pinky’s Rock n Rolla on July 11 in Richmond Hill NY: a rugged 4 mile trail through 100 year old pines and Queens longest oak forest. All finishers get medals, top three earn prizes, dogs welcome, and proceeds benefit Puppy Kitty NYCity.

Soapstone Assault is a rugged 5.5 mile trail race with six steep climbs and about 1500 feet of climbing. Field limited to 50 runners and parking is tight, making this an intimate but fierce challenge with post race breakfast sandwiches.

Ridge Reaper Trail Runs on Aug 1, 2026 at Ward Pound Ridge, a scenic preserve 50 miles north of NYC. Choose 25K, 50K or 50 mile timed courses on technical singletrack and wide carriage roads with ridge views.

Interstate 17 is a challenging 17 mile trail run on August 8, 2026 in Closter NJ that traces Hudson River viewpoints. Expect rugged technical singletrack, steep climbs and boulder scrambles across four loops with fully stocked aid stations.

Experience the Stonington Cross Country 5K at Stonington High School, a scenic route from the track through campus streets and wooded trails to a field finish. Family friendly with a kids half mile for ages 10 and under.

Join an 8 hour trail gathering at Crandall's Park and run as many 5K loops as you like. Potluck, raffles, prizes and a Shenipsit Striders 50th anniversary gift for those who complete at least one loop.

Run the Jug End Loop Ultra on August 22, 2026 at Jug End State Reservation in Egremont MA, a six hour timed event on a scenic, hilly 4.2 mile loop through woods and an apple orchard. Rack up laps, earn a handmade mug and support local chari..

Tackle the Shawangunk Ridge Trail near Rosendale NY for sweeping Hudson Valley views across cliffs, sky lakes and rocky ridgelines. Choose 70 Miler, 30 Miler or half marathon for a rugged, self supported navigation challenge.

Run for The Hills is a 4th annual trail 5K on September 12, 2026 at Oswegatchie Hills Nature Preserve, winding around Clark Pond. Expect exposed rocks and roots on scenic trails while helping support preserve maintenance.

Macedonia Trail Race at Macedonia Brook State Park offers scenic single track and forest trails with climbs and viewpoints. Choose 50K, 25K or 12K for a rewarding day of trail running in Connecticut.

Experience a three day trail running festival at Wawayanda State Park in mid September 2026 with races from a 1 mile kids run to a 100 mile ultra. Free camping and a partnership with Bigger Than The Trail support community and mental health..

Tackle the Hook Mountain Ultra, a rugged multi loop trail outing in Upper Nyack, NY that crowns each circuit with a climb to the Hook Mountain summit. Choose marathon or 50 mile distances and enjoy panoramic Hudson River views and big eleva..

Run the newly restored Moosup Valley State Park Trail in Moosup CT with 5K, 10K and a kids fun run on Sunday September 27, 2026. Postrace medallions or tee shirts, food and drink, leashed dogs welcome, and proceeds benefit the Rotary Club o..

Tackle an Everesting relay across 61+ miles and 29,029 feet of climbing at Mohawk Mountain in Cornwall CT, with a 72 hour window to run, hike or walk. Team up and test endurance on this epic fall challenge.

Iron Hike Fall Double Kuwohi Trail Marathon Plus Relay is a timed 24 hour trail challenge covering more than 28 miles with epic elevation at Mohawk Mountain in Cornwall Connecticut. Choose solo or relay, run, hike or walk and chase a big da..

Tackle a scenic 5K or 8K through Pindar Vineyards on flat packed trails while supporting the NY Cancer Foundation. Finish with live music, food trucks and a complimentary glass of Pindar wine for a festive fall celebration.