Trail Running calendar near Upton 2025-2026

The Wildcat 5K Trail Run-Walk-Wag is an annual event held in Boxford, Massachusetts, starting and finishing at the Danvers YMCA Camp overlooking scenic Stiles Pond. The race features separate courses for runners and walkers, including those..

The Fitzwilliam to Troy Depot Day Cheshire Rail Trail Fun Run will take place in Fitzwilliam on Saturday 6 June 2026. You can run 5 miles.

Enjoy the Nipmuck South Trail Race in Mansfield CT, a 15.7 mile out and back along the Fenton River that winds through woods, fields and over small bridges. Organized by Shenipsit Striders, proceeds benefit local trail stewardship.

Join the Stonington Cross Country 5K in Pawcatuck CT on Wednesday August 12 2026 for a free community race that blends one track loop, quiet campus roads and scenic trails. A children's 1/2 mile for ages 10 and under also finishes on the sc..

The Old Goat Track Club XC Classic will take place in Sutton on Sunday 23 August 2026. You can run between 5 and 5 kilometers.

Trail Animals Running Club Fall Classic at Great Brook Farm State Park offers scenic trails and distances from 10K to 50 mile, plus a youth fun run and Mischief Mile. Aid stations and vegan options support runners in this cupless event.

The Run for the Hills - Niantic will take place in Niantic on Saturday 12 September 2026. You can run 5 kilometers.

The Moosup Valley 10K All Trail Race will take place in Moosup on Sunday 27 September 2026. You can run between 5 and 10 kilometers.