Trail Running calendar near Westport 2026-2027

Early morning trail run in Gay City State Park offering 3, 5 and 8 mile races. The 8 mile is part of the Blue Blazed and USATF CT MUT series and includes teams of three competing for prize money.

Stone Tower Half Marathon is a 13.1 mile trail race in Lynn Woods Reservation run as three identical loops that pass the historic Stone Tower. The course features forested singletrack, rocky trails and carriage roads and emphasizes environm..

The TARC Blue Hills Skyline Trail Run will take place in Canton on Saturday 11 July 2026. You can run 12 kilometers.

A 5.5 mile trail race at Soapstone Mountain featuring six ascents and about 1500 feet of climbing. The route circles the mountain with multiple steep rocky sections, limited aid access, and a field limited to 50 runners due to parking.

An evening cross-country event at Stonington High School on August 5, 2026, featuring a 5K and a Children's 1/2 Mile for ages 10 and under. The course starts and finishes on the track and includes campus streets, trails, grass, and a bridge..

The Tarc Summer Classic will take place in Medfield on Saturday 8 August 2026. You can run between 10 and 40 miles.

Run trails on a 5 km loop for 8 hours at Crandall's Park. It's a potluck celebration with food, raffles, and games. Complete loops to earn tickets for prizes and a commemorative gift.

The Watermelon Wobbler is a 5k trail run/walk/hike through scenic conservation land and a working farm. It features a varied off-road course and supports local agriculture. On-site parking is supplemented by a satellite lot nearby.

The Old Goat Track Club XC Classic is a 5k cross-country race at Waters Farm in Sutton. It features separate men's and women's races and is the opening event for the USATF New England XC Grand Prix. Enjoy a team tent area, awards, and a pos..

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

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

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.

This 5K trail run takes participants through the scenic trails and grasslands of Goddard Park in Warwick. The flat course is open to all ages and abilities. Registration includes a T-shirt and ample parking is available.

Experience a 100% trail run on the newly restored Moosup Valley State Park Trail. Choose between a 10K or 5K race, with a free Kids Fun Run also offered. Your participation supports local community initiatives through the Rotary Club.

The Run for the Pumpkins Trail Run will take place in Westerly 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 Connecticut with a two person relay option. The route follows a 13 mile segment of the Nipmuck Trail and relies on blue blazes for navigation.

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..

The Wine Run offers a scenic 3-mile trail run through Sakonnet Vineyard. After the run, participants enjoy dinner, wine, and live music on-site. The event also includes non-running dinner options for adults and children.

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.