Trail Running calendar near Pleasant Valley 2026-2027

Experience the wooded trails of the historic Ward Pound Ridge Reservation in New York. This event offers 25K, 50K, and 50 mile distances featuring a mix of technical singletrack and runnable carriage roads.

Experience an obstacle course with over a dozen mud pits at the 508 INTL Adventure Sports Center. Enjoy a non competitive environment featuring music, food, and a festive atmosphere for both participants and spectators.

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 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.

The third annual Tappen Brook 5K in Bridgewater, CT, uses newly opened trails through Bridgewater Town Park with packed dirt and natural paths and views of Lake Lillinonah. Participants receive a race-day gift and top finishers earn prizes.

A community eight hour trail event of roughly 5K loops at Crandall's Park in Tolland, CT on August 15, 2026. The day includes a potluck, raffles per loop with prizes, and a 50th anniversary gift for runners who complete at least one loop.

Trail races at Fahnestock State Park near Cold Spring NY offer three distances on mixed runnable dirt roads and technical single track. Multiple aid stations and a post race meal are provided and proceeds support park conservation.

A 6 hour loop ultra and a 4.2 mile memorial run at Jug End State Reservation in Egremont, MA on August 22, 2026. The 4.2 mile trail runs through woods, fields and an apple orchard with about 830 feet elevation per lap.

This 4-mile trail run in Schenectady Central Park uses a flexible time trial format. All proceeds support addiction recovery services, honoring a personal legacy. A pre race stretching session is included.

Trail races at Thacher State Park on August 23, 2026, with 10K, half marathon, marathon, and 50K options that share the same opening 10K loop. The event is cupless with multiple aid stations and race day packet pick up.

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 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco on August 23, 2026, with start and finish at the Fox Lane High School campus and a non-perishable food collection for the Mt. Kisco Food Pantry.

Ocean State Ultra is a loop trail event at Big River Management Area in West Greenwich, Rhode Island offering 100 mile, 12 hour and 6 hour races. The course uses 10 mile loops with trails, short pavement sections, and staffed aid stations.

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.

A family friendly 5k obstacle race at Stratford Short Beach on September 5, 2026, featuring more than 18 obstacles with sand and water elements. The event raises funds for Sterling Community Center programs and supports team and individual..

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.

A trail event in Rosendale, NY on the Shawangunk Ridge Trail offering 70 mile, 30 mile, and half marathon divisions. The course crosses varied terrain and is minimally supported so participants must carry food and water purification.

Trail race at Macedonia Brook State Park on 13 September 2026 featuring single-track forest trails, climbs, viewpoints and three distances: 50K, 25K and 12K.

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 Hook Mountain Ultra is a demanding 50-mile or 27-mile trail race in Upper Nyack, NY. The course features repeated loops with significant climbs, ridge running, and scenic Hudson River views. It includes full aid station support and has..