Trail Running calendar near Litchfield 2025-2026

Enjoy a scenic off road 5K through beaches, vineyards, ponds and forests at Hallock State Park. Choose in person or virtual and bring kids to a fun run while supporting the Long Island Greenway and enjoying post race wine for ages 21 and up..

Join the 9th annual Fall Back Into The Trails Series at Red Wing Recreation Area in Lagrangeville on Nov 1 and 2, 2025 with options from a single 10k to a rugged 100k across looped trails. Aid, camping and custom finisher medals await.

Event information The People in Need - Day of the Dead 5K is scheduled for Sunday, November 2, 2025, in Fresh Meadows, New York. The event is a charity 5K walk/run organized to raise funds and awareness for People in Need. The event locatio..

Run or stroll through historic Alice Newton Street Park at the Woodbridge Trail Run plus Woodland Walk, with a challenging two loop 4 mile course and an easy 2 mile walk to the falls. Participants receive custom tech T shirts and post event..

Join the Day of the Dead Charity 5K in Fresh Meadows to support People in Need and services for immigrant communities. Enjoy a family friendly two lap course through Cunningham Park with awards for top finishers.

Challenge yourself at Steep Endurance's 8 Hours at the Farm in Brookfield, a rolling 4 mile loop of single track and farm trails. Choose 8 hour, 4 hour, or 4 mile distances, enjoy finisher swag, and support local nonprofits.

Run a chip timed 5k through scenic Stonington Vineyards and celebrate with a wine pour at the finish. Registration includes a soft tee, collapsible wine glass and finisher medal while supporting the Alzheimer's Association.

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.

Join the 45th Annual Veterans Cross Country 4K at the Northport VA Golf Course on Nov 8 to run a scenic grass course and support hospitalized and homeless veterans on Long Island. Post race snacks, awards, and fun runs add family appeal.

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.

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 the Centerville Bank Thompson Turkey Trot on November 9 for a family friendly cross country 5K, 3K Wobble walk and kids fun run with costumes encouraged. Proceeds benefit Thompson trails, parks and the local food pantry.

Taconic Road Runners FDR Park Cross Country Run is a cross-country race held in Yorktown Heights, New York, at FDR Park. The event features a 6K course that includes almost two miles of the park’s trail system, with most of the route on sof..

USATF Long Island hosts an 8K cross country championship at Bethpage State Park on Nov 9, 2025 for adults 18 and over. Competitive team and individual racing with medals and live results make for a great fall race.

Run the 19th Annual Age Before Beauty 5K cross country at White Memorial in Litchfield, Connecticut on Sunday, November 9, 2025. Enjoy a scenic conservation trail course that welcomes all ages and abilities.

Run the Never Stop Running Foundation Long Island Turkey Trail Trot, a scenic 5K through Bethpage State Park on Nov 15, 2025. Family friendly with a kiddie dash and proceeds benefiting local youth and athlete development.

Enjoy a runnable 5k loop through pine corridors and rolling trails in Manorville, NY, perfect for runners, hikers and walkers. Choose 3 hour, 6 hour or 12 hour options at this inaugural race with an aid station, training runs and early swag..

Run the Brookhaven Trail Half Marathon or 5 Mile through single track, fire trails and sandy woodlands at Brookhaven State Park near Wading River NY. Half marathoners vie for cash, a wood finisher medal and post race refreshments.

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.

Take on the Fall Fling 400 at YMCA Camp Sloper in Southington CT on Nov 22, 2025. Choose a unique 400 minute loop endurance challenge or a 4 mile two lap trail race through wooded single track and rolling hills.