Trail Running calendar near Highland Park 2026-2027

Trail races in Fahnestock State Park near Cold Spring, NY on August 15, 2026, offering 50K, 25K, and 5.5‑mile options with aid stations, a post-race meal, and proceeds supporting park conservation.

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..

An untimed 3.1 mile vineyard run plus a short kids run at Bishop Estate Vineyard & Winery in Perkasie, PA, featuring grass trails, a finisher's medal, onsite wine and grape juice tasting, food trucks and activities. Proceeds benefit the Hil..

A mud-free 5 km stadium obstacle race at Citizens Bank Park on August 29, 2026, featuring 20 obstacles, stadium stairs and a finisher medal. The event also includes a kids race, spectator options and team registration.

A 50K trail ultramarathon in Forest Park, Queens. The race is 12 laps of a 2.5 mile counterclockwise loop with about 300 ft climb per lap, aid stations after each lap, and an eight hour cutoff.

Clothing optional 5.5K and 1 mile fun run at Sunny Rest Resort featuring mixed trail and road courses, resort access, and age group awards.

A USATF-NJ Open and Masters cross country championship over a 5K course at Natirar Park in Peapack Gladstone on August 30, 2026. Registration opens July 1, entry is $40 with a $5 USATF-NJ discount and no day of registration.

A community 5K trail run and One Mile Move As You Please at Thorncroft Farm in Malvern on September 3, 2026. Cross-country courses include varied terrain and obstacles, with an after-party featuring live music and food trucks and proceeds s..

An outdoor day at Masker's Barn in Feltville combining self guided trail routes, a Trail Treasure Chase, and a five hour Barn party with BBQ, drinks, games, crafts and music.

Celebrate Labor Day at William Heritage Winery with a scenic 5K trail run or a 1 Mile walk. Enjoy live music and vineyard views while participating in chip timed races for all ages in Mullica Hill.

Kingwood Ultras is a loop trail event near Frenchtown, NJ where runners use a two mile circuit with a central base camp. Distances range from 10K to 100 miles and timed formats up to 48 hours, with handcrafted wood awards.

City Challenge Race returns to Jersey City on September 12, 2026 with a fast 3-mile urban obstacle course featuring 20+ city-style obstacles, new finisher medals, professional chip timing, 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.

Trail events at Hart Scout Reservation in Pennsburg include 12h, 6h and 4h timed options, a 6-mile hike and a virtual race supporting the local scouting council, run on mostly double-track and single-track wooded trails with hills and natur..

A fourth annual 5-mile trail run around Leaser Lake paired with a 100-yard youth Dragonfly Dash, family educational activities, shirts, refreshments, a midway water station, and prizes.

Timed 5k at Blue Ridge Estate Vineyard and Winery in Saylorsburg on Sept 13 2026, with event swag, an on course wine pour, age group awards, and virtual options.

Experience a scenic 5K race and yoga session at Penns Woods Winery. Enjoy a chip timed course through vineyard trails and national park land followed by live music and wine.

Wicked Fast Marathon & Half Marathon Poconos runs along the Lehigh River on the D & L Trail with a consistent net drop of about 1%. Both distances are USATF certified and finish at the Outdoor Center in Lehighton.

The Corporate Fun Run Pier 84 Manhattan will take place in New York on Monday 14 September 2026. You can run 5 kilometers.

A weekend trail festival in Ringwood State Park featuring a 100 mile race with a 36 hour cutoff, multiple shorter distances, Friday panels and film screening, free camping, and nonprofit partnerships supporting mental health.