Trail Running calendar near New Shoreham 2026-2027

Run a scenic 3-mile trail through vineyards and farms at Westport Rivers Winery. After the race, enjoy a dinner with wine and live music. All runners receive a souvenir wine glass.

A community 5K trail run, walk and hike in Eisenhower Park Milford on June 7, 2026 supporting the Milford Rotary and the Beth El Center. The course uses a high school cross country route with mostly flat sections and some rolling hills.

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.

Test your endurance on a 4.25-mile loop in Hamden, CT. Set a goal from a marathon to 50 miles within the 12-hour window. Your registration supports local trail maintenance and comes with unique swag.

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..

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

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..

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 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.

Run a scenic 5K trail race through 300 acres of natural terrain at Winding Trails in Farmington. Compete for age group awards and the local Lee Chisholm Award on a course surrounding Walton Pond.

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.

Run an 8K or 5K through the autumn scenery of Pindar Vineyards on a flat trail course. Your entry includes chip timing, a tech shirt, and a post race party with wine, music, and food. The event supports the NY Cancer Foundation.