Trail Running calendar near Stafford 2025-2026

The Jug End Loop Ultra will take place in Great Barrington on Saturday 22 August 2026. You can run 4 miles.

Hit the fields at Waters Farm on Sunday, August 23, 2026 for the Old Goat Track Club XC Classic, a fast and friendly 5K cross country through scenic farm trails. A USATF New England Grand Prix stop with race day registration available.

The TARC Fall Classic will take place in Carlisle on Saturday 5 September 2026. You can run between 10 and 50 miles.

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 technical single track and big climbs at the Macedonia Trail Race in Kent, Connecticut. Choose 12K, 25K, or 50K loops with Cobble Mountain views and rugged trails for a rewarding, scenic challenge.

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.

Experience the Iron Hike Fall Series, a four day trail festival in Cornwall, CT from October 1 to 4, 2026, featuring epic ultra distances and relays. Run, hike, or walk timed courses that test endurance and celebrate grit.

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.

Run scenic, rooty trails in Groton Town Forest on October 4 with 9.5 mile and 3.4 mile options through rolling hills and rocks. Limited to 250 runners with refreshments and awards.

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.

Run the Midstate Massive Ultra Trail on October 10 to 11, 2026 across central New England, a UTMB Index point to point ultramarathon along the Midstate Trail. Choose 100 mile, 50 mile or 50K courses that wind through mountains, fields and r..

Conquer Mohawk Mountain on scenic but rugged trail courses with 5K, 10K, half marathon and marathon options, big climbs and singletrack. Runners earn finisher medals, enjoy aid stations and follow a cupless policy to reduce waste.

Celebrate the 20th Wayland HFC Striders Cross Country Festival on October 11, 2026, a family friendly meet supporting Wayland High School programs. Youth 3K plus open 5K races, trophies and local sponsors make for a fun community day.

Enjoy a scenic 3 mile trail run at Sakonnet Vineyard in Little Compton on October 17, followed by wine, BBQ, live music and a souvenir wine glass. Adults 21 and up get timed racing, a race shirt and a festive post race party.

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.