Trail Running calendar near Simsbury 2025-2026

Blue 2 Blue Challenge is a rugged 50K through New Haven trails, with about 6350 ft of climbing and technical rocky terrain including a summit at Mt Sanford. Expect a cutoff driven, no frills race for seasoned trail runners.

Take on the Dandelion Dash 5K or the Mushroom Mile on The Hartsbrook School trails, with a virtual option available. Muddy, scenic terrain and proceeds support the school's Land Stewardship program.

Run the Mount Archer Trail Race Sunday May 3 2026 in Lyme CT with a scenic 9.2 mile loop or a 3 mile option for runners and walkers. Chip timing, aid stations, and proceeds support Lyme emergency services.

Run the rugged Wapack Trail in Ashburnham MA with 21.5, 43, or 50 mile options on May 9, 2026. Limited entries for this technical, scenic trail run benefit land conservation through the Trail Animals Running Club.

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.

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.

Explore trails around Soapstone Mountain and Shenipsit Forest at the Soapstone Mountain Trail Races in Stafford Springs, CT on May 17, 2026. Pick a half marathon or 6K, support local trail stewardship, and register January 1, 2026.

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 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.

Run a scenic 5 mile Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on Saturday, June 6, 2026. Enjoy family fun, food, and festivities while supporting the Fitzwilliam and Troy historical societies.

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..

Manitou’s Revenge is a rugged 53 mile ultramarathon through the Catskill Mountains on June 20, 2026, featuring roughly 15,000 ft of climbing and technical, often remote terrain. Expect limited aid and a true test of endurance and trail skil..

Notchview Ultra invites runners July 10 to 13, 2026 in Windsor, MA, offering formats from 100.7 miles down to 6 hour on a scenic 1.9 mile loop. Enjoy frequent aid, camping, swag, and proceeds supporting local conservation.

Tackle Soapstone Assault, a rugged 5.5 mile trail race up Soapstone Mountain in Somers CT on July 26, 2026, featuring six steep climbs and about 1,500 feet of climbing. Expect rocky, technical terrain and stunning summit views.

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.

Join the Sweltering Summer Ultra, an 8 hour track challenge at Clapp Park in Pittsfield where runners and walkers lap a cinder loop and hit a marathon split. Chip timing, live leaderboard, refreshments and awards support the AYJ Fund.

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.