Trail Running calendar near West Rock 2026-2027

A winter trail party on a 5K loop offering 5K, 3 hour, 6 hour, and 3 hour rucking divisions, with proceeds benefiting the South Mountain Conservancy. The course mixes carriage roads and technical singletrack with about 300 feet gain per loo..

A onesie-themed 5K at Ramapo Valley County Reservation on February 14, 2027, run on a flat scenic loop around Scarlet Oak Pond. The event is capped at 200 participants, has no cutoff, offers adaptive support, and includes a finisher medal.

Trail races on a 10 mile loop at South Mountain Reservation offering 50M, 50K, 20M and 10M with marked trails, three aid stations per loop, timing, SWAG, and awards for top three male and female finishers.

A multi-loop trail race at South Mountain Reservation offering 11M, 20M, 50K and 50M options on three marked loops with varied terrain, significant elevation gain, a single finish-area aid station, and support for the South Mountain Conserv..

A chip timed 5K at Osprey's Dominion Vineyards in Peconic, NY on March 20, 2027. Entry includes a t-shirt, collapsible wine glass, finisher medal, chip timed bib and a pour of wine.

A trail 5K and free kiddie run at Bethpage State Park with soft trails, event shirts, post race refreshments and a virtual option; proceeds support the Never Stop Running Foundation.

On March 28, 2027 this roughly 16 mile out and back follows the Nipmuck Trail through Yale Myers Forest and Bigelow Hollow State Park. Registration opens Jan 1, 2027, parking is limited and a waitlist is used.

A community 5K run and walk at Bethpage State Park on scenic soft trails, with a free kiddie run and a virtual option. Proceeds support the Never Stop Running Foundation.

A point to point 123 mile ultramarathon across Connecticut from East Thompson to Southport with trail and road sections, a 36 hour cutoff, relay options, and staffed aid stations.

A mountain trail event at Harriman State Park on April 3, 2027 offering a half marathon, a 10K and a 10K ruck on rugged technical trails with significant elevation gain. Entry is capped at 400 and proceeds support trail maintenance.

Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT features a 25K loop with 3K+ of vertical and a 50K two-loop option. The course mixes technical singletrack and carriage roads, includes aid stations, and follows a cupless..

A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

A 5K trail run and walk in Blydenburgh County Park, Smithtown, NY held in April. The course uses mixed trail surfaces, offers on-site refreshments and hydration, supports Last Chance Animal Rescue, and includes dog-friendly park rules.

Trail races at Penwood State Park with a one loop 17K and a three loop 50K, about half on technical single track. The course is rocky and rolling, organized by the CT Trailmixers with proceeds to local land trusts.

A women-centered trail event at Lake Mohegan offering 5K, 10K, and a 4-hour loop on a 3.2 mile trail. The race is open to non-binary runners, follows a cupless aid policy, and includes finisher medals and post-race refreshments.

Two trail events, 25K (about 17 miles) and 10 miles, on technical singletrack and crushed gravel around the Shawangunk Ridge near Ellenville NY. Routes feature steep climbs, two aid stations, a six hour cutoff and a 150 runner cap.

Squatchywaska Mountainfest in the Shawangunk Ridge on April 24, 2027 features a technical 25K and a 10 mile lollipop course with steep climbs, rocky singletrack, two aid stations, and a six hour cutoff.

A spring 10K trail race in Cross River NY on April 25 2027, organized by Leatherman's Loop Races. Entry is by lottery with registration Jan 8 to Jan 11 2027 and the $58 fee includes the park entry.

VCP 50K is a looped trail ultramarathon in Van Cortlandt Park on 01 May 2027. The 50K course starts with a flats lap then ten cross country loops, with stocked aid stations, drop bag access, finisher medal, singlet, meal and beer.

Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.