Trail Running calendar near Niantic 2025-2026

Join the Darien Depot Overstuffed Turkey Trot at Darien High School on Nov 28 for 5K, 1 mile and kids races on scenic cross country trails, with medals for all finishers. Proceeds support The Depot youth center and post race music and food.

Join the Leftover Turkey Trot, a lively trail 5K at Bethpage State Park with in person and virtual options plus a free kiddie dash. Proceeds benefit the Never Stop Running Foundation and support youth and special needs programs.

Run or walk the Never Stop Running Foundation Turkey Trot, a scenic trail 5K at Belmont Lake State Park on November 30, 2025, supporting a great cause. Enjoy post race refreshments and a 50 50 raffle with proceeds benefiting the foundation.

Take on the Tower Tag Challenge at Sleeping Giant State Park on December 6 with 4 hour or 8 hour timed options of repeated out and back laps to the park observation tower. Enjoy the scenic climb, earn a finisher medal, and support the park.

Tough Cookie 8K at Sunken Meadow State Park offers scenic cliffside views of the Long Island Sound, festive cookie stops and a post race cookie fest. All paces welcome and proceeds support local charities.

Run the Frosty Forest 5K in Stratford through Roosevelt Forest on an off road trail welcoming runners, joggers and walkers. Holiday costumes encouraged, every finisher gets a commemorative item and proceeds support local charities.

Run until only one remains at SRC Presents: A Backyard Ultra in Blydenburgh County Park on December 13 and 14, 2025, looping a rugged 4.167 mile trail. Day and night loops, limited crew access, and proceeds support the Long Island Greenbelt..

Join the 8th Annual Taco Trials in Rocky Hill: eat a taco then run a 1 mile loop, repeating it ten times for a fun, quirky challenge. Medals for finishers and proceeds benefit the Connecticut Forest and Park Association.

Seth's Fat Ass 50K at Forest Park in Springfield is a friendly challenge of up to ten 5K loops. You have seven hours to run as many laps as you like, grab event schwag and a t shirt, and enjoy the social ultrarunning vibe.

Tackle the TARCtic Frozen Yeti at Hale Education in Westwood MA on Feb 7 and 8 2026 with a 30 hour challenge or a 15 mile looped race. Expect well marked winter trails, regular aid and proceeds supporting land conservation.

Run the Never Stop Running Foundation 4 Leaf Clover 5K at Bethpage State Park on March 8 2026 for a scenic trail 5K across grassy polo fields and winding soft trails. Family friendly with a kids run, virtual race and refreshments.

Enjoy a scenic 5K around Osprey's Dominion Vineyards in Peconic, NY on a two lap cross country style course for runners and walkers. Finishers get a shirt, bottle stopper medal, shatterproof wine glass and a wine pour.

Run the scenic single track loop at Hale Reservation in Westwood, MA with 3.5 mile or 6 hour options. Trails, pond views and wood bridges await while proceeds support land conservation.

Run a scenic 16 miles on the Nipmuck Trail in Union Connecticut, out and back to the Boston Hollow turnaround through Yale Myers Forest. Field is capped at 100 and proceeds benefit local trail groups.

Tackle the Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT on March 29, 2026 with 25K and 50K options across rugged singletrack and big climbs. Expect steep scrambles, more than 3,000 feet of gain per loop, cupless aid s..

Run Across CT 123 is a point to point ultramarathon across about 123 miles of Connecticut, weaving trails and backroads through 25 towns. Choose 100K or 200K solo or relay and chase a coveted belt buckle for 200K finishers.

Join the Bunny Trail 5K at Bethpage State Park for a family friendly run starting on a grassy polo field and winding onto scenic soft trails. In person and virtual entries plus a free kiddie run support the Never Stop Running Foundation.

Run a scenic 6.55 mile quarter marathon through West Hartford Reservoir 4 as two loops around the park. Limited to 150 runners, the event features chip timing, post race treats and awards in five year age groups.

Join Run for the Rescue on April 11, 2026 for a scenic 5K through Blydenburgh County Park with on site and virtual options. Tackle varied trails, enjoy post race refreshments, and support Last Chance Animal Rescue.

Join the John Jay Community Trail Race on Sunday April 12 2026 in Cross River NY for a scenic 5k on wooded trails, a 4k community walk and a 200 meter kids dash on the track. Early preregistered participants get race shirts.