Trail Running calendar near Old Lyme 2025-2026

Join the 45th Annual Veterans Cross Country 4K at the VA Medical Center golf course on November 8, 2025. Scenic grass course, a free half kilometer fun walk, awards and snacks with proceeds supporting hospitalized and homeless veterans.

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.

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.

Run the Upton 10.5K or Half Marathon on scenic single track trails in Upton State Forest. Limited to 250 runners, enjoy challenging climbs, aid stations, a TVFR trail buff and cozy post race soup and fire pits.

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.

Join the Dave Driscoll 19th Annual Age Before Beauty 5K cross country at White Memorial in Litchfield on Sunday, November 9, 2025. Enjoy a scenic all cross country course as the first race of the day ahead of the Junior Olympics.

Run through pine corridors and soft needle paths on a runnable 5k loop with 270 feet of climb per lap in Manorville NY. Choose a 3, 6, or 12 hour challenge, enjoy a stocked aid station, and support the Long Island Greenbelt.

Run or walk a scenic 5K at Bethpage State Park for the Never Stop Running Foundation Turkey Trail Trot, with a free Kiddie Dash and virtual option. Join November 15, 2025 to support the foundation and enjoy post race treats.

Run scenic trails around Watchaug Pond at Burlingame State Park with 8 mile and 4 mile options in the Lil Rhody Runaround. Close out the WTAC Fall Race Series while soaking up classic New England fall scenery.

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.

Take on the Baystate Dirty Dog Trail Run Ruck Walk 5k in Berkley on November 16, a rugged, possibly muddy trail where you can run, ruck with a pack, walk, or bring a leashed dog. Proceeds support local beagle and K9 charities.

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.

Hit the Brooksvale Trails Turkey Trot at Brooksvale Park in Hamden for scenic 5K and 10K trail runs that are friendly to runners and walkers. Enjoy swag and maple bacon donuts while supporting park trails and a local food drive.

Tackle an accurately measured 8K cross country course through the MDC Reservoir Complex in West Hartford on Sunday, November 23, 2025. Rolling gravel and trail terrain with a touch of pavement make this a scenic challenge for all paces.

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.

Join the Roxbury Thanksgiving Charity Race, a scenic 5K in Roxbury, Connecticut, starting and finishing at Everett B. Hurlburt Community Park. Run or walk to celebrate the season and support local causes.

Make Thanksgiving morning active at the Turkeywacker 5K in Wrentham, a festive trail run at Rice Recreation Complex with donuts, cider and raffle prizes. Awards for top finishers across ages ensure competition and family fun.

Celebrate Thanksgiving on the trails at the F.I.T. Turkey Trot Trail Race in Cumberland, Rhode Island on November 27. Choose from 5K, 5 Mile, combo, multilap or a Kids Race and earn a unique finisher medal.