Trail Running calendar near Trumbull 2026-2027

A trail running festival at Ward Pound Ridge Reservation near Cross River NY offering 25K, 50K, and a 50 mile option across wooded singletrack and carriage roads. The race includes finisher medals, awards, food and beverages.

Timed loop events at Tamaques Park in Westfield NJ offering 3 hour, 6 hour, 9 hour, 12 hour and 24 hour options. One loop is 0.8 miles and runners can choose pavement or gravel; 24 hour entrants follow extra night rules.

A community cross country meet at Stonington High School offering a 5K and a children's 1/2 mile. The course mixes track, quiet campus streets, trails, grass, and finishes back on the track.

Experience a technical seventeen mile trail run along the Hudson River cliffs with over five thousand feet of elevation change. High endurance is required for this rugged course featuring boulder scrambles and scenic river views.

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.

A forested 5K on the new trails at Bridgewater Town Park in Bridgewater, CT. The 3rd annual event features mixed natural terrain, views of Lake Lillinonah, participant gifts and awards for top finishers.

Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.

A community running event in Tolland, CT featuring a marked 5K trail loop run repeatedly over an eight hour period, potluck food and grill items, raffle tickets awarded per loop, and a 50th anniversary gift for runners who complete at least..

Trail races in Fahnestock State Park near Cold Spring, NY, offering 50K, 25K and a 5.5-mile course on varied terrain with on-course support, post-race meal, and proceeds supporting land conservation.

A timed 5K at Brimfield Winery on August 15, 2026, run on a mostly grass cross country style course. Registration options include a standard 5K with a postrace wine pour and a volunteer plus run option.

A 6 hour timed ultra and a 4.2 mile memorial run at Jug End State Reservation in Egremont MA on August 22, 2026. The loop covers woods and orchards with 830 feet elevation per lap and benefits Louison House and Dana Farber.

On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are co..

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.

Barn B Q Trail Festival on Saturday 9/5/2026 at Masker's Barn pairs a trail run or hike with a five hour barn party featuring BBQ, drinks, music and games. Ticket options cover adults, designated drivers, and children.

Sterling Down & Dirty 5K is an annual family friendly obstacle race on Stratford Short Beach each September. Participants tackle more than 18 obstacles, join teams to fundraise for the Sterling Community Center, or volunteer on race day.

A multi-division trail event on the Shawangunk Ridge near Rosendale NY offering 70 mile, 30 mile and half marathon options on an unsupported, fully blazed route with shuttle access and finisher shirts and medals.

An urban obstacle race on the Jersey City waterfront on September 12, 2026. The event features a fast 3 mile course with 20 plus city-style obstacles, chip timing, new finisher medals, awards, and free race photos.

Experience a diverse trail race at South Mountain Reservation featuring fire roads and single track trails. Choose from multiple distances ranging from a 5K to 50 miles with aid stations every three miles.

A group, end-to-end run along the Farmington Canal Heritage Trail from West Suffield to New Haven, roughly 56 miles, raising funds for Mental Health Connecticut. The route is largely flat and unsupported with a 14 hour completion cut off.

Trail race at Macedonia Brook State Park in Kent, Connecticut on September 13, 2026. Courses of 12K, 25K and 50K on single track forest trails with steep climbs, technical sections and cupless aid stations.