Trail Running calendar near Kent 2025-2026

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..

Take on a rugged 5K loop at South Mountain with 5K, 3 hour, 6 hour and kids 1 mile options, plus a rucking division. This fun fundraising trail event supports the South Mountain Conservancy and delivers rocky climbs and fast singletrack.

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...

Squatchapple is a scenic, challenging trail race at South Mountain Reservation with 11, 20, 50K and 50 mile options run on three looped courses. Limited to 400 runners and often sold out, the event benefits the South Mountain Conservancy.

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.

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 is a rugged trail race at Harriman State Park offering a half marathon and 10K with ruck divisions on technical singletrack and steep climbs with Hudson River and NYC skyline views. Limited to 400 runners.

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 in East Islip offers 25K and 50K point to point runs along the Long Island Greenbelt from Sunken Meadow to Heckscher Park. Expect varied trails, five aid stations and a requirement to do two hours of trail work or donate $20.

Squatchywaska Mountainfest in Ellenville NY on April 25, 2026 features 25K and 10 mile trail races with steep climbs, technical singletrack, and views of Verkeerder Kill Falls. The 150 runner cap promises a rugged, intimate mountain running..

Wawayanda Trail Fest in Hewitt NJ offers distances from a half marathon to 100K on a scenic 26 mile loop of single track, gravel roads and rhododendron tunnels. Expect good aid support, camping and finisher awards for a true trail festival..

Leatherman's Loop is a popular 10K trail race held annually in the spring at Ward Pound Ridge Reservation in Cross River, New York. The event attracts runners aged 7 to 107 and features a scenic course through natural trails. Due to high de..

Join the 52nd Jack Bristol Lake Waramaug Ultra Races in Kent CT on April 26, 2026 for 50K, 50 mile or 100K loops around scenic Lake Waramaug. Expect friendly aid stations, post race food and classic New England views.