Trail Running calendar near Rocky Point 2025-2026

The Santa's Summit 10k is a scenic and challenging trail run held at Bull Run Marina in Clifton, Virginia. The course follows the Bull Run Occoquan Trail, featuring hilly terrain with a mix of out-and-back and one-way sections. Participants..

Test your endurance at the Tower Tag Challenge in Sleeping Giant State Park with 4 hour and 8 hour timed options on repeated 3.3 mile loops to the Observation Tower. Bring your own cup, enjoy finisher swag, and support the park.

Event overview The PPTC Endurance Fest takes place in Prospect Park, Brooklyn, NY on Sunday, December 7, 2025. The event offers two distance options: 50 Miler 50k Registration closes on Thu, December 4 at 11:59 PM ET. Course and event ser..

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...

Event overview MCW The Holmdel Classic is a trail race held on December 13, 2025, at Holmdel Park in Monmouth County, New Jersey. The event offers loop-based distances on a multi-lap course: Loop: 4.65 miles Halfish : 3 loops 50 kmish : 7..

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..

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 the iconic ridgeline at Sleeping Giant State Park on March 29, 2026 with 25K and 50K options that loop scenic singletrack, technical sections and a steep rock scramble up to the Observation Tower. Aid stations will be staffed but this c..

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.