Trail Running calendar near Stratford 2025-2026

SRC Presents: A Backyard Ultra takes place at Blydenburgh County Park in Hauppauge, NY on December 13–14, 2025. The event features two races: A Backyard Ultra, a true ultramarathon where runners must complete a 4.167-mile loop within an hou..

Event overview The Frosty Forest 5K takes place in Roosevelt Forest in the Town of Stratford, Connecticut on Saturday, December 13, 2025. The event is a trail run over a 5K distance. Participants may wear holiday costumes during the event...

South Orange, New Jersey hosts the NJ Trail Series SOMO Winter 2 on Saturday, December 13, 2025. The event offers three distances: 5K, 10K, and 13.1 miles, run on a looped course through South Mountain Reservation. The course blends fire ro..

Run Seth's Fat Ass 50K on Saturday December 20 2025 at Forest Park in Springfield MA, a friendly looped ultra offering one to ten 5K laps with a seven hour cutoff. Relaxed vibe, easy parking and race day registration welcome runners of all..

Event overview The West Rock Winter Fat Ass Extravaganza is scheduled for December 28, 2025 in Hamden, CT near Lake Wintergreen. The event is an eight-hour looped run using a 1.6-mile loop around Lake Wintergreen with about 65 feet of eleva..

Join the Frosty Fat Sass at South Mountain for scenic yet rugged trail running and hiking with a 5K or 3 and 6 hour options on rocky, rooty singletrack. This self supported fundraiser benefits the South Mountain Conservancy.

Event overview The Squatchy Onesiefest 5K is scheduled for February 14, 2026 at Ramapo Valley County Reservation, starting and finishing at the New York-New Jersey Trail Conference (NYNJTC) Headquarters. The event has a onesie theme; awards..

The Febapple Frozen event is a trail running race held in South Mountain Reservation, Maplewood, New Jersey. Scheduled for February 21, 2026, it offers multiple distance options including a 50-mile, 50-kilometer, 20-mile, and 10-mile race...

Event details Squatchapple takes place on March 7, 2026 in West Orange, New Jersey at the Tulip Springs Trailhead on Cherry Lane. The event offers the following distances: 50 miler 50K 20 Miler 11 Miler Registration closes on March 6 at 1..

Livingston Oval Ultra : March 7, 2026 The event in Livingston, NJ at Robert Harp Drive is a timed loop ultra on the town Oval. It is the third annual running and adds a 12-hour distance for 2026. Distances offered: 12 hours 6 hours 3 hours..

Event overview The Ospreys Dominion Wine Run 5k is scheduled for Saturday, March 21, 2026 in Peconic, NY at Osprey's Dominion Vineyards (44075 Main Rd, Peconic, NY 11958). The event is a 5k run/walk open to ages 1 through 99. The event is c..

Event overview The Enchanted Forest Ultra Run is a trail ultramarathon held at Roosevelt Forest, 700 Peters Lane, Stratford, CT. The event is offered as a 6-hour format and as a 50K distance. Field size is limited to 50 participants. Regist..

Run 16 miles of rugged single track through Bigelow Hollow and Yale Myers Forest to Boston Hollow in this intimate, capped trail race near Union, CT. Limited to 100 runners, the event supports local trail organizations.

The Morris County Empanada Trail Run, held in Morris Plains, NJ, offers both 5K and 10K run/walk events on scenic trails within Central Park of Morris County. The course features mixed terrain including dirt, grass, gravel, and some hills,..

Event details The Sleeping Giant Trail Runs take place March 29, 2026 at Sleeping Giant State Park, 200 Mt Carmel Ave, Hamden, CT. The event offers these distances: 25K 50K (two loops of the 25K loop) Registration closes March 27. Entry f..

Big Bear Squatch North at Harriman State Park offers a rugged half marathon or 10K over technical trails with steep climbs and scrambling on April 4, 2026. Proceeds support the New York New Jersey Trail Conference and trail care.

The Spring SOMO Timed Trail Races take place at South Mountain Reservation in South Orange, New Jersey. This event features a looped trail course of 1.88 miles (just over 3K) that includes single track, pavement, and fire road sections. Run..

John Jay Community Trail Race is a community running event in Cross River, New York, on the John Jay Community Cross Country Trail. The event features a 5k Trail Race, a 4k Jay Walk, and a Kids Jay Dash, a 200-meter race. The 5k winds throu..

Run scenic singletrack at Penwood State Park in the Traprock 17 km and 50 km Ultramarathon, a friendly community race with short and long course options. Race day is the Saturday before the Boston Marathon.

Shore2Shore : Apr 18, 2026 Shore2Shore in East Islip, NY is a point-to-point trail race offering the following distances: 50K 25K The race uses the Suffolk County Long Island Greenbelt Trail. The 50K course runs from Sunken Meadow on the..