Trail Running calendar near Woodbury 2026-2027

A 5K trail and obstacle run on the 400 acre campus of Gaylord Specialty Healthcare in Wallingford CT, featuring 24 obstacles and a festival area with vendors, live music, and food trucks, supporting the Gaylord Sports Association.

Experience a scenic evening run on a flat paved loop around Rockland Lake. This chip timed half marathon features sunset views, frequent aid stations, and custom finisher medals only 45 minutes north of NYC.

Six hours of looped trail running at Ansonia Nature Center on Saturday June 13, 2026. The course uses roughly 1.9 mile singletrack laps with about 170 feet of elevation gain per lap and is limited to 69 runners.

Trail races of 50k, 30k and 10k through western Massachusetts hill towns on single track and dirt roads, held in partnership with Franklin Land Trust and featuring aid stations, first aid and locally produced awards.

Turf Wars 2026 at Chelsea Waterside Park in New York is a Tone House multi zone athletic competition on June 13, 2026. Individuals, doubles, and four person teams move through three timed Zones and finish with a Wild Card event.

The 5th Annual iBE-FiT 5K Invitational at Van Cortlandt Park offers an in-person 5K and a virtual 5K option, a two-loop course with flats and hills, medals for all finishers, and proceeds supporting local community programs.

A trail 5K and 10K at Pleasant Valley Wildlife Sanctuary on June 13 featuring mixed single-track and carriage-road terrain, water stations, finish-line food and music, and proceeds supporting local conservation.

A community event at Camp Edey on June 13, 2026 featuring a 5K run/walk and a 1 mile family walk, Family Day activities, race amenities, and age-group awards to benefit Girl Scouts of Suffolk County.

A community 5K at Hampshire Regional High School combining paved roads and technical wooded trails, plus a one mile fun run around campus; post race refreshments and awards are provided.

Trail races at Mansfield Hollow State Park: a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K trail loop. Proceeds support Connecticut trail stewardship groups.

A community 5K trail run, walk, and hike at Eisenhower Park in Milford on June 14, 2026, on a high school cross country course. The event supports the Milford Rotary and Beth El Center and includes music, water, snacks, awards, and T shirts..

A weekly cross country series offering thirteen 5K races on Tuesday nights from April to July. The event takes place at Central Park in Parsippany and is open to all ages and abilities. Participants can register for the full series or pay f..

A 53 mile, 15,000 foot ultramarathon in the Catskills from Windham to Phoenicia featuring long technical sections, limited aid stations, a 23 hour time limit, bus transport to the start, and packet pickup in Phoenicia.

A morning trail run at Gay City State Park on June 20, 2026, offering 8 mile, 5 mile and 3 mile races. The 8 mile joins regional trail series and includes team competition with prize money.

Test your endurance at Elka Park with this 14.5 mile weighted event. Participants navigate over 5,000 feet of elevation gain while carrying a 20 pound pack through the New York landscape.

The Jade's Belmont Plateau 5K will take place in New York on Saturday 20 June 2026. You can run 5 kilometers.

A loop trail run at Lawson Lake Park on June 20, 2026, featuring a 1.25 mile course with lake and creek views. Options include 2.5M, 5M, a one-hour format, and team entries; awards and a meal ticket are included.

A 5K through Camp Jewell’s roads and wooded trails including a covered bridge, plus a free one mile kids run. Pre entry is $30 before June 6 and increases to $35 afterward.

A loop-format trail event in Adams, MA where runners choose one, two, or three loops on machine and hand-built singletrack. Proceeds support Thunderbolt Ski Runners' stewardship of trails around Greylock Glen and Mount Greylock.

A weekly cross country series offering thirteen 5K races on Tuesday nights from April to July. The event takes place at Central Park in Parsippany and is open to all ages and abilities. Participants can register for the full series or pay f..