Trail Running calendar near Glenwood 2026-2027

Participate in a free USATF sanctioned 5K trail run or walk at The Heron Farm and Events Center. This family friendly event features live music and various awards for finishers and age group winners.

Explore the scenic trails of Monroe County during this four part mid week race series. Enjoy chip timed runs through various local parks along with post race cookouts and custom series participant awards.

A point to point 100k+ trail race in Naples, NY, through mostly single track in the Finger Lakes. The course has a 20 hour cutoff, 11 aid stations, and serves as a UTMB and Western States qualifier.

The Black Diamond Express Trail Races on August 23, 2026 run on the Lehigh Valley Trail in Mendon, NY, offering a 5K and a USATF certified half marathon. The event is organized by the Mendon Foundation with Monroe County Parks.

Trail runs and walks on August 29 2026 at Phillips Creek State Forest offering 5K, 10K, and a newly added 25K over varied forest trails with creek crossings, mud, and rolling terrain.

Raid the City is a three hour urban navigation race in Hamilton where teams of two collect points at checkpoints across trails, roads, alleys and parks. Teams must run on foot and use a smartphone app to track checkpoint visits.

Experience a scenic run through the woods and around the Howard Eaton Reservoir on a mix of gravel roads and single track trails. Choose between 5k, 10k, and half marathon distances to support local youth programs.

Trail races at Ontario County Park in Naples NY offering a long and a short course listed as a half marathon and a 5 mile option, with camping, evening social events, post race food and vendors, and volunteer incentives.

A community wellness event at Sprague Brook County Park on September 12, 2026 featuring a 5K trail run and a 2 mile non timed walk, with proceeds supporting the Bread of Life Outreach Center and keepsake blankets for early registrants.

Experience a non competitive trail run or walk through 63 acres of scenic trails at a therapeutic riding facility. Choose between 1km and 5km distances and earn a completion medal while supporting a local nonprofit.

Adventure Tails 5K is a dog-friendly community run and walk at Campground Adventures in Hinsdale, NY. Fifty percent of proceeds benefit the Cattaraugus County SPCA while participants use scenic trails and visit local vendors.

UNFINISHED is a Backyard Ultra at Woodbine Beach Park on September 12, 2026 featuring repeated 6.71 km loops. Options include Backyard Ultra solo or teams of three, a 15 hour Endurance window, and a community Sunshine Yard.

A community fundraiser at Mendon Ponds Park with in-person and virtual 5k options plus a Trail X Challenge and a 10k combo. The event supports ROCovery and includes event swag and packet pick up dates.

A 5K and 10K trail run in Letchworth State Park on September 13, 2026 featuring woodland courses, finisher medals, a post-race celebration at Trailside Lodge, and timed results with downloadable certificates and photos.

A community run through the vines at Palatine Hills Estate Winery featuring a timed 5 km race, untimed family and dog walks, post-run food and music, and winery perks. A portion of proceeds supports Community Care.

Multi-day timed ultras at Shortsville Reindeer Farm on a one mile grass and trail loop. Multiple timed options, an on-course aid barn, and belt buckles for finishers who complete 100 loops; proceeds support ROCovery Fitness.

A one mile loop elimination challenge in Webster NY on September 20, 2026 where runners must meet shrinking time cutoffs each mile; finishers receive a medal and category pins, with cash prizes for top male and female.

A 5K trail run on Bella Rose Vineyard grounds in Lewiston with a stemless wine glass and complimentary wine tasting for participants 21 or older. The event features professional timing, finish line photos, music, and on site parking.

Experience the rolling hills and dense forests of Pennsylvania at the Marilla Reservoir. This event features off road courses ending at a historic covered bridge with proceeds supporting local trail maintenance and development.

A chip timed trail event in Hamilton with distances from 1 km kids runs to a technical 21 km on the Bruce Trail. Cupless aid stations, included Canadian toque and optional medals for purchase.