Trail Running calendar near Glenwood 2026-2027

A looped trail weekend in Ancaster offering 10K to 100 mile events on 20 km loops with over 500 m elevation per loop and four aid stations. The 100K and 100 mile races offer Western States qualifying opportunities.

The Mills Miles is a Last Runner Standing event at Powder Mills Park in Pittsford, NY featuring repeated one mile loops with time cutoffs, a final all out lap, post-race BBQ and awards, and fundraising support for TrailsROC.

A single-day endurance walk at Holiday Valley, Ellicottville on May 24, 2026, offering 7, 14, 21, or 28-mile options with optional 10/20/35 lb rucking, a 10-hour finish window, well-marked trails, and regular aid stations.

A budget-friendly midweek trail series across four Monroe County parks offering single-race entries or an all four series option. Features chip timing, a post-race cookout, series scoring and awards plus a custom hat for series entrants.

Trail run in Boutwell Hill State Forest near Cherry Creek New York offering 6k, 12k, 26k and 52k routes. The event raises funds for the Chautauqua County Equestrian Trail System and includes aid stations for the longer distances.

A four-week, 90-minute trail running series for runners comfortable with about 3 miles. Sessions cover warm-ups, guided runs, hill and footwork drills, gear and safety, and include trail socks and gifts.

Trail runs in Naples NY with a rugged 25K single loop around the Cumming Nature Center and Honeoye Inlet Wildlife Management Area and a more runnable 10K. Proceeds support environmental education at the RMSC Cumming Nature Center.

A 38th annual trail event in St. Catharines featuring a 21.1 km half marathon and a 7 km trail race with limited fields. The routes include the 12 Mile Creek Trail and Hydro Hill and support the Niagara Rankin Cancer Run.

A farm-based ultrarun on 06/06/2026 at Fish's Farm Market in Shortsville, NY where participants run or walk as many 1.52-mile loops as they wish. Timing, aid station, medals, prizes and raffles; proceeds benefit Colony Caregivers.

Join an inclusive superhero themed event at Seneca Park featuring a 5K road run and a paved one mile walk. Celebrate the mission of the Rochester Hearing and Speech Center with family activities and ice cream for all participants.

Trail races at Mendon Ponds Park on a 4 mile loop with an 8 mile two loop option. The course is off road with about 350 ft of elevation gain per loop and requires runners to carry their own fluids.

Commemorative run in Niagara-on-the-Lake honoring General Józef Haller and the Blue Army, with races from 1 km to 10 km along the Niagara Parkway Recreational Trail. Race kit items, finisher medal and a prize draw for a flight to Poland.

A checkpoint-style trail race in Toronto on June 13, 2026, organized by Slowpokes with The North Face, featuring an approximately 10-15 km route, checkpoint navigation, and a morning post-race party with coffee, food, DJs and prizes.

A 45 mile all trail ultra in Letchworth State Park that follows both sides of the gorge. It includes a relay option and multiple aid stations with remote stretches between stations.

A timed 15:23 trail event at Marydale Park featuring an approximately 3.7 km loop, a relay option for teams up to five, one aid station per loop and race kit gels and a finisher medal. The event is listed as sold out.

A mud obstacle trail run at Holiday Valley in Ellicottville, NY with 15 obstacles and three course options including a kids race. Courses follow the ridgeline past Spruce Lake and all finishers receive medals.

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 community organized trail race in Naples, NY featuring a half marathon loop with an option to run a marathon by doing two loops, varied terrain through High-Tor Wildlife Management Area and downtown, and multiple staffed aid stations.

Timed 12 hour and 24 hour ultraruns plus 12 hour and 24 hour relay options on a mostly paved one mile loop at Rochester Rotary Sunshine Camp, with a staffed aid station, flexible relay rules, and an optional personalized bib.

SKECHERS Wicked Wine Run in Buffalo takes place at Liberty Vineyards & Winery on July 18, 2026. The event features a 1K tasting walk and a 5K run or walk with on-course tastings, event shirts, and finish line wine.