Trail Running calendar near Roxbury 2026-2027

Experience a 5K cross country run or walk through the mowed trails of Peach Hill Park. Reach the highest point in Poughkeepsie for panoramic views and enjoy post race snacks and awards.

A two day family obstacle event at Obstacle Wonderland in Wallkill featuring adult sprint and multi lap endurance formats, plus kids 50 m and 1 km courses, finisher medals, podium awards, and a charity presence.

A loop based backyard ultra at Trenton Fish and Game Club where runners repeat a 3 1/3 mile trail lap each hour until one runner remains or the 30 hour limit is reached, with milestone patches and a $120 entry fee.

A multi-day elevation endurance series at Mohawk Mountain in Cornwall Connecticut from June 4 to 7 2026. Events range from a 12 hour 15 mile challenge to 84 hour ultras with solo and team FlexRelay formats.

A 12-hour trail event in early June 2026 at Overlook Trailhead near Moreau beach featuring a 3.8-mile loop with a steep staircase climb. Participants can run solo, form relay teams, or enter a Fun Run of one to three laps.

A Spartan obstacle race weekend at Bethel Woods on June 6-7, 2026 featuring Sprint, Super and Kids races, an obstacle workshop, on-site camping, and team entry options.

An annual community 5k and kids run that raises suicide awareness and supports families; offers in-person and virtual 3.1 mile options and a 1 mile kids run.

Fourth edition mountain event at Plattekill in Roxbury, NY on June 7, 2026. It offers a 6.5 miles mountain course with 3500 ft gain and a 5k with 1000 ft gain early and a downhill finish.

A flat, non technical trail 5K at Schodack Island State Park on June 7, 2026, with kids races, post race music and a BBQ. Entry fees rise by registration period and kids races cost five dollars each.

Experience a day of trail running and mountain biking at the Norbrook Farm Brewery Trail Festival. Enjoy multiple race distances, local food trucks, and rewards at this scenic Connecticut brewery.

A trail 5K and 10K at Pleasant Valley Wildlife Sanctuary on June 13, 2026, with routes on single track trails and carriage roads. Proceeds support Mass Audubon conservation; water stations, finish area refreshments, and limited parking.

A 53 mile ultramarathon through the Catskills with about 15,000 feet of climbing, technical rocky trails, long unsupported sections and nine aid stations. The race requires self sufficiency and does not permit pacers.

Test your endurance at Elka Park with this 14.5 mile weighted event. Participants navigate over 5,000 feet of elevation gain while carrying a 20 pound pack through the New York landscape.

A looped trail event at Lawson Lake Park on June 20, 2026, offering 2.5M, 5M and a one hour format. Entry includes a shirt and post race food; individual and team awards recognize top finishers and most laps completed.

A 5K through Camp Jewell’s roads and wooded trails including a covered bridge, plus a free one mile kids run. Pre entry is $30 before June 6 and increases to $35 afterward.

A loop-format trail run in Adams, MA, offering one to three loops and a separate 5 km meadow option on varied singletrack and hiking trails; proceeds support Thunderbolt Ski Runners trail stewardship around Greylock Glen and Mt. Greylock.

Five Monday evening 5K trail races at Town of Wilton Camp Saratoga across June to August 2026. Entries available per race or as a series package; proceeds benefit the Wilton Wildlife Preserve & Park.

An 8.6 mile trail run at Minnewaska State Park Preserve on June 24 with chip timing and commemorative towels for finishers. Entry is limited to 250 runners and parking carries a 10 USD per car fee.

An obstacle course backyard ultra where athletes run an approximately 3 miles loop every hour until one remains. Solo and relay formats are available, with a 50 mile solo option and team relays for groups of three to six.

A night 5K at Lakeside Park with mixed trail terrain, reflective markers, and required personal lighting; finishes receive handmade medals and proceeds benefit the Pawling Recreation Department.