Trail Running calendar near East Hampton 2026-2027

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..

Test your endurance on a 0.355-mile track loop for 8 hours at Clapp Park. Enjoy a unique bottle-drop aid station and support the AYJ Fund for children with cancer. Awards celebrate all age groups and lifetime achievements.

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..

The Running Wild at Wildwood Trail 2.5 Mile Trail Run/Walk will take place in Wading River on Saturday 8 August 2026. You can run 3 miles.

Explore the new trails of Bridgewater Town Park at the Tappen Brook 5K. This community trail run on August 9, 2026, offers a scenic course through woodlands with views of Lake Lillinonah. Participants receive a gift, and top finishers win p..

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.

Explore the varied trails of Fahnestock State Park in New York with a choice of 50K, 25K, or 5.5-mile races. The event includes course support, a post-race meal, and supports park conservation through its non-profit organizer.

Experience a scenic off-road trail run or walk through the conservation lands of White Barn Farm. This cup-less 5k event supports local sustainable agriculture and community food security in Wrentham.

Run the Jug End Loop Ultra in the scenic Jug End State Reservation. Choose between a 4.2-mile race or a 6-hour ultramarathon on a challenging loop trail. All finishers receive a handmade ceramic mug, and the event supports local charities.

Experience a classic 5k cross country race through the scenic fields of Waters Farm in Sutton. Join the USATF New England Grand Prix season opener on a spike friendly course with both open and masters divisions.

A rugged trail race of about 6.5 miles through Westmoreland Sanctuary near Mount Kisco, NY, with finisher medals, age group prizes, on site signup options, and a food collection for the Mt. Kisco Food Pantry.

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 Stratford’s dirty day on the beach at this 5k obstacle race featuring 18+ challenges through sand and water to support the Sterling Community Center.

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

Experience the rugged beauty of northwest Connecticut at Macedonia Brook State Park. Featuring single track trails and views of the Catskill Mountains, this event offers 12K, 25K, and 50K distances for trail runners.

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.

The Where the Pavement Ends trail race offers a technical 4.25-mile single loop or an 8-mile double loop through the Hemlock Hills. It's part of the multi-race Trail Mix Series. Both races start and finish at the Lake Windwing ballfields in..

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.

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.