Trail Running calendar near Smithtown 2026-2027

A point to point 5K in East Hampton beginning at the Connecticut Draft Horse Rescue with shuttle transport from Center School. Bib pick-up is at Center School gym and awards are presented by age group after the race.

Experience a unique four mile trail race through the historic Forest Park in Queens. Run along naturally carved glacial terrain and pine groves with your dog to support a local animal rescue organization.

A new 1.776 mile loop trail race at Putnam Memorial State Park in Redding, CT, run mainly on carriage trails with some singletrack. Entry fees are listed between $50 and $80 and registration opens December 19, 2025.

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..

Experience a midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

A one-mile out-and-back on the Farmington Canal Heritage Trail in East Granby, offered in two waves and hand timed, on crushed gravel. Limited parking and a $25 registration fee; all proceeds benefit charities.

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 timed trail event at South Mountain Reservation on July 25, 2026, where runners draw colored golf balls to determine each loop; charitable proceeds support Bigger Than The Trail and aid stations will provide Skratch Hydration.

A third annual cross country event in Warwick, NY on July 25, 2026, featuring a mass-start 5k and a non-timed 400 m Kids Dash with finishers ribbons.

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 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.

Honoring September 11 heroes, this arena climb at TD Bank Ballpark features a 2,200 foot track through stadium aisles. Join a timed stair challenge or a flat concourse walk to support the Tunnel to Towers Foundation.

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.

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.

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..

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.