Trail Running calendar near Pawcatuck 2025-2026

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..

Tackle the Fall Trailblazer Ultra at White Barn Farm in Wrentham with 12, 24 or 36 miles of rugged single track through conservation land and features like Knuck Up Hill and Pinnacle Rock. Cupless event so bring your own water.

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 21st annual GFRC Busa Bushwhack on November 2, 2025 in Framingham, tackling scenic, technical trails in Callahan State Park over 5.3 or 10 miles. Finish at Brophy Elementary, grab a cooling towel and compete for log trophy awards.

Get muddy and celebrate at Hoppy Trails 6K on November 8 at Adams Farm in Walpole, MA. Two scenic wooded loops finish with a beer garden, food trucks and adidas demos for a fun post race party.

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.

Run scenic single track and forest roads at the Upton 10.5K and Half Marathon, a hilly, technical trail challenge in Upton State Forest. Enjoy a small field, post race fire pits, hot soup and chocolate, and support local charities.

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.

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 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.

Join the Dirty Turkey 5K in Plymouth on Nov 16 for a scenic ocean view run along the Grace Trail, finishing at Historic Cordage Park. Post race enjoy local food, vendors and a complimentary Dirty Water Distillery drink for 21 and over.

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 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.

Run or walk this Thanksgiving on a scenic 5k trail around Scoville Reservoir in Wolcott with medals, swag and timed results. Enjoy pre race stretching and free post race yoga, family and dog friendly, with proceeds supporting EndoFound.