Trail Running calendar near Billings 2026-2027

ENDURE Last Man Standing in Bethpage State Park asks runners to repeat a fixed 4.2 mile loop each hour; finish within the hour to continue. Laps continue with progressively shorter cutoffs until one runner remains or the event window ends.

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 outdoor obstacle event in Wallkill, NY offering adult sprints and multi-lap endurance races plus kids’ sprint and 1 km courses, finisher medals, age-group awards, a nonprofit Teddy Bear Crawl presence, and on-site youth fundraisin..

A choose your own adventure ultra and trail event at Chesterfield Gorge with multiple distances, lap based 50k to 100mi options, a 30 hour window for ultras, and timed 33k and 11k races the following day.

A weekly cross country series offering thirteen 5K races on Tuesday nights from April to July. The event takes place at Central Park in Parsippany and is open to all ages and abilities. Participants can register for the full series or pay f..

A weekly Tuesday evening cross country series at Waveny Park with varied distances and formats, including predicted time races, relays, handicaps, a luminaria finish, and age-graded awards.

A weekly 5K cross-country trail series at Worthington Winery in Somers, Connecticut, held Wednesdays from June 3 to July 1, 2026. The course runs through backwoods and vineyard areas with views of ponds and a covered bridge.

Multi-day elevation based endurance events at Mohawk Mountain in Connecticut, June 4 to 7, 2026. Solo, Trail Buddy and Trail Family formats cover timed events from a 12-hour 15-mile option up to 84-hour 152+ miles with large elevation gain.

A point to point trail event on the New England Trail offering 112 mile and 50 mile options. Self supported with crew, navigation by blue blazes, technical traprock terrain and typical finish windows of 30 to 45 hours.

Experience a timed 5K trail run or walk through the scenic woods and fields of the Van Vleck Farm and Nature Sanctuary. Enjoy live music and food trucks at this annual community event in Woodbury.

A road and trail event at Rockwood Hall in Rockefeller State Park Preserve featuring a 10K and a 1K kids race. The course follows wide carriage roads with Hudson River views and wooded sections, and proceeds support carriage road maintenanc..

Obstacle course races at Bethel Woods Center for the Arts combine rolling trails, forests, and multiple obstacles across Sprint, Super, and kids formats, with workshops, camping, volunteer options, and spectator access during the weekend.

The Levee Loop Trail Race 10K - Islip will take place in Islip on Saturday 6 June 2026. You can run between 5 and 10 kilometers.

Paired 5K paved loop and 10K mountain trail at Rockland Lake State Park in Valley Cottage, NY. The 5K is a flat, fully accessible lake loop; the 10K climbs about 1,300 ft on rocky, steep terrain and includes one aid station.

A mountain trail event in Roxbury, NY on June 7, 2026 offering a 6.5 mile race with 3500 ft gain and a 5k with a steep opening climb and downhill finish, with awards and finisher swag.

A women-only 5K obstacle mud run in Riverhead, NY on June 7, 2026, featuring 18+ obstacles and open to females aged seven and older; participants may run, jog, or walk the course.

A free trail 5K in Shirley Chisholm State Park in Brooklyn on June 7, 2026, organized by Black Men Run NYC. Registration is free with an optional $25 singlet fee and runs March 31 to June 4, 2026.

Trail races at Ward Pound Ridge Reservation on June 7, 2026 include a 13.1 mile half marathon and a 10K, both passing the summit where the historic fire tower is being reconstructed. The event also raises funds for the Friends of the Fire T..

Run for RMC on June 7, 2026 at Stanley Park in Westfield MA offers a 5K trail run and a 1 mile accessible route to raise awareness of renal medullary carcinoma and support related programs.

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.