Trail Running calendar near Westport 2026-2027

Run for a cause in Dunstable, Massachusetts. Choose the 5-mile race or challenge yourself in the 6-hour event on a scenic loop with significant elevation. This trail race benefits the Humane Society for Greater Nashua.

Explore the trails of Mansfield Hollow State Park at the Nipmuck South Trail Race. Choose between a scenic 15 mile out and back route or a new, challenging 5K course. Proceeds support local trail stewardship organizations in Connecticut.

Celebrate the longest day of the year with a trail run in Hebron, Connecticut. This event on June 20, 2026, features three distance options on the trails. Choose from a 3 mile, 5 mile, or 8 mile course.

Run a scenic yet rugged half marathon trail race at Lynn Woods Reservation in Massachusetts. This 13.1-mile event features three challenging loops showcasing the historic Stone Tower. The focus is on sustainability and a centralized start/f..

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

A unique trail race at Soapstone Mountain featuring six ascents. Runners circle the base and climb each upward trail they find, finishing with the infamous Killer Hill. The challenging course includes rocky and steep terrain.

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..

Experience the Trail Animals Running Club Summer Classic at Medfield's Noon Hill and Shattuck Reservations, a scenic and challenging 10 mile loop of forested singletrack that climbs to a Noon Hill vista. Distances include 10 miles, 40 miles..

Join an 8-hour celebration run on a 5K trail loop in Tolland, CT. Earn raffle tickets for each loop and enjoy a community potluck. All participants receive a special 50th-anniversary 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 annual Vineyard Hill Trail Run features a scenic 5K/10K course over Vineyard Hill and through Bradley Palmer State Park. It's part of the North Shore Trail Series and includes a fully marked trail with an aid station.

Challenge yourself on a 10-mile loop course through the Big River Management Area in Rhode Island. Choose from 100-mile, 12-hour, or 6-hour ultra distances on a relatively flat trail. All participants receive a race sweatshirt, with a speci..

Traverse the scenic ski slopes and forest trails of Wachusett Mountain in this timed event featuring loops from 7 to 28 miles. Earn a finisher medal within 10 hours and enjoy a post trek party at the mountain base.

Experience a scenic 5k trail run or hike through the Oswegatchie Hills Nature Preserve in Niantic featuring views of Clark Pond and natural woodland terrain.

Join the Trail Animals Fall Classic at Great Brook Farm for scenic trails and distances from youth fun runs to 50 mile ultras. Community vibe, limited spots, and on course aid make this a favorite, so bring your own hydration and register e..

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.

Run the Moosup Valley All Trail Race on September 27, 2026. Choose from a 5K, 8K, or 10K on the 100% trail course at Moosup Valley State Park. After the run, enjoy post-race food and a choice of a shirt or medallion.

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.

Experience a scenic trail run or walk through Ryan Park in Rhode Island to support the North Kingstown Firefighters Association with medals for top age group finishers.