Trail Running calendar near Wrentham 2026-2027

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.

Join the Charlie Stavros Memorial Beach Run on September 15, 2026 in Westerly, Rhode Island, a free 3 mile beach run honoring a beloved local runner. Enjoy a scenic low tide out and back along Westerly Town Beach with friends and family.

A trail race in Hooksett on September 19, 2026, featuring a 5k on stone dust and wooded conservation trails and a half mile kids run for ages 12 and under. Proceeds support Hooksett Kiwanis community and youth programs.

The Ocean State XC Invitational will take place in East Greenwich on Saturday 26 September 2026. You can run 5 kilometers.

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..

The Run for the Pumpkins Trail Run will take place in Misquamicut on Saturday 3 October 2026. You can run between 5 and 10 kilometers.

Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes wit..

A 26.4 mile trail marathon in Ashford, CT with a two runner relay option, varied trail terrain and defined course cutoffs including an 8 hour finish limit.

Enjoy autumn trails at the Keene Family YMCA Fall Foliage Trail Races on October 4, 2026, with 5K and 10K options around scenic Keene, NH. Run for community impact while enjoying chip timed courses and seasonal views.

Point to point UTMB Index ultratrail across central Massachusetts with 100 mile, 50 mile and 50 kilometer options, wave starts, and seeded pacing to coordinate aid station support.

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

Enjoy a scenic 3 mile trail at Sakonnet Vineyard, then celebrate with wine, dinner, music and a souvenir wine glass. BBQ only and kids BBQ options are available for those who prefer to skip the run.

Tackle the Trail on October 17, 2026 is a point to point trail race along the Air Line Trail State Park between Willimantic and Putnam. Distances include marathon, relay marathon, half marathon and 10K with four staffed relay stations.

A multi distance trail event on October 17 and 18, 2026 in Brookline NH along the Granite Town Rail Trail, featuring a 30 hour ultramarathon and a 30 mile night race. All profits support local trail conservation.

A looped trail race at Wompatuck State Park near Hingham, MA offering a 10 Miler and a 50K with mixed single track, wider trails and some paved sections. Aid stations, cupless policy, participant donations, and proceeds support charity part..

The Grills Trail Run will take place in Misquamicut on Saturday 24 October 2026. You can run between 10 and 10 miles.

The Pumpkin Pacer 5k will take place in Wrentham on Saturday 24 October 2026. You can run 5 kilometers.

A mountain race in Keene, NH featuring four repeated climbs and descents on mostly ski trails and some single-track, totaling 4.9 miles and 1650 feet of elevation. Proceeds support the Keene Community Kitchen and prizes are awarded.

TARC Stone Cat Trail Festival in Willowdale State Forest (Ipswich, MA) offers looped trail distances from 10K to 100K, a Cider Donut Mile and a free youth fun run, with proceeds supporting local land stewardship.

Enjoy scenic trails around Watchaug Pond at the Li'l Rhody Runaround on November 15, 2026, with 8 mile and 4 mile course options. Part of the WTAC Fall Trail Race Series, it welcomes runners of all levels.