Trail Running calendar near Milford 2025-2026

Run the scenic Pocantico Hills Marathon or Half Marathon on Nov 8 2025 in Sleepy Hollow NY, a loop through Rockefeller State Park Preserve with rolling hills and Hudson views. Proceeds support local park and trail groups.

Run a scenic 10K up Mt Beacon to the firetower and back on rugged Hudson Highlands trails with steep climbs and autumn views. Part of the Beacon Bonfire festival, the race ends with refreshments, a shirt and festival perks.

Celebrate Veterans Day with a scenic 5K at Tyler State Park in Richboro and help fund scholarships for American veterans. Choose the 3.1 mile race, a 1 mile fun run, or a virtual option for all abilities.

Take on the Raven Rocks 10k trail race at Ward Pound Ridge, starting in the meadow and climbing to Raven Rocks Overlook and the Fire Tower Summit. Enjoy rugged woods, a rewarding downhill finish, and support for Friends of Trailside Museum.

Join Taconic Road Runners for a relaxed 6K through FDR Park on November 9, 2025, now held as a club fun run and meeting. Enjoy soft trails, commemorative running gloves and hot drinks by the warming fire while you meet fellow runners.

Join a 24 hour vigil run at Kean University honoring those who served while keeping someone on the track for the full day. Proceeds support Mission 22 and its veteran wellness programs.

Take on the treacherous six mile trail at Cheesequake State Park in the 45th annual HASHATHON on November 9, 2025. Support local EMS charities and celebrate afterward with pizza, beer, raffles and prizes.

Join the Red, White and Run 5K trail run and walk at Veteran's Memorial Park in Lackawaxen on November 15, 2025. All paces welcome with day of registration and awards for top finishers across age groups.

Run Staten Island's scenic singletrack at NYC Trail Mix on Nov 15 2025, weaving through Blood Root Valley, High Rock and La Tourette. Choose 50M, 50K or half marathon distances and support the Greenbelt Conservancy.

Hit the trails at South Mountain Reservation in South Orange on November 15, 2025 for NJ Trail Series SOMO Winter 1. Choose from 5K, 10K or 13.1M looped routes featuring fire roads, single track and rolling hills.

Join the 8th annual Bill Bruno Alumni Cross Country Run at Holmdel Park on November 15, 2025 for community 5K and 3K races. Expect team and individual competition, chip timing, and a commemorative mug for the first 150 entrants.

Hit the trails at the Red, White and Run 5K in Lackawaxen's Veteran's Memorial Park on November 15, 2025. Enjoy a scenic trail run or walk, friendly competition, and awards for top finishers across age groups.

Chase a fast PR at the Last Chance XC Championships in Oak Ridge Park, Clark NJ on November 16. The USATF New Jersey 8k championship runs on a double loop pancake flat course, with personalized bibs, oversized medals and free action photos.

Run scenic, hilly single track at the Tarrywile Half Marathon on November 16, 2025 in Danbury CT with 10K, half marathon and marathon options. Rugged terrain, aid stations and finisher medals make for a rewarding trail day.

Join the Old Bridge Sayreville Rotary Club for a 5K trail run and walk on Sunday, November 16, 2025 at Sayreville Sports Complex to support veterans housing. Rain or shine event with dog tags for all and shirts for preregistered runners.

Join a lively 5K at Clifton City Hall on Sunday, November 16, 2025, featuring a race T shirt and postrace music, raffles and healthy snacks. Age group awards and special recognition for first responders add extra excitement to this 500 poin..

Brave frosty singletrack through scenic Ringwood woods with 5K, 10K and half marathon options for every trail runner. Finish with a warm post race party serving food, drinks and winter views.

Join the 4th Annual Sargent Elementary Turkey Trot in Beacon, NY for a family friendly 5K on the scenic Long Dock Park trails plus a Kids Fun Run on campus. Enjoy a food drive, live DJ, refreshments, awards and new team sign ups.

Tackle scenic single track and rolling climbs in the FEAR Trail Fest 5 mile at Lewis Morris Park on Nov 23, 2025. Open to first timers and seasoned trail runners, with limited spots, prizes and free course previews before race day.

Join a scenic trail 5K or bring kids to a fun run at Hilltop Hanover Farm, a historic working farm and environmental center. This family fun fundraiser gives 5K finishers a $5 farm stand credit and supports the Friends of Hilltop.