Trail Running calendar near Waterbury 2025-2026

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..

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..

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 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.

Run Across CT 123 is a scenic 123 mile ultramarathon across Connecticut from East Thompson to Southport, weaving through forest trails and backroads. Enter as a timed solo or relay team and challenge yourself to finish within the 36 hour cu..

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..

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.

XTERRA New Jersey is an off-road multisport event held at the scenic Wawayanda State Park, featuring over 40 miles of trails and a clear lake. Part of the XTERRA World Tour, it offers a variety of races including trail runs (5K to 42K), gra..

The VCP50k is an ultramarathon held in Bronx, New York, founded in 2023 and designed to accommodate both novice and experienced runners. The race features a challenging yet accessible course consisting of ten loops on the classic Tortoise a..

Event overview The Blue 2 Blue Challenge is a 50K trail event in New Haven, CT on May 3, 2026. It is held as an out-and-back that starts at West Rock Playground and follows the blue-blazed trail system. Organizers report a slightly over 80%..

The Dandelion Dash will take place in Hadley on Sunday 3 May 2026. You can run 5 kilometers.

Breakneck Point in Beacon, NY on May 3, 2026 is a rugged trail race that challenges seasoned runners with steep, technical terrain and dramatic views. Expect solid aid station support, post race food and memorable swag across 14 or 26 miles..