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Trail Running Calendar near Smithtown 2026-2027

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Explore the top trail runs near Smithtown for 2026-2027! We've gathered 28 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

April 2027
Apr
3
Sa

NSRF The Bunny Trail 5K

Trail Run Walk 5 km
A community 5K run and free kiddie run at Bethpage State Park with trail terrain, a virtual option, and donations benefiting the Never Stop Running Foundation.
Apr
10
Sa

Run for the Rescue 5K Trail Run/Walk

Trail Run Walk 5 km
A 5K trail run and walk at Blydenburgh County Park in Smithtown, NY on mixed surfaces through park trails. The event supports Last Chance Animal Rescue and includes onsite hydration, restrooms, same day results and photos.
Apr
17
Sa

Shore2Shore - East Islip, NY

Trail Run 25 km 50 km
Shore2Shore in East Islip, NY on April 17, 2027 follows the Greenbelt from north shore to south shore and offers 50K and 25K distances.
Apr
24
Sa

Lake Mohegan Women's Trail Race

Trail Run Walk 5 km 10 km
Women and non-binary runners take on 5K, 10K, or a timed 4 hour loop on the trails around Lake Mohegan in Fairfield, CT.
May 2027
May
15
Sa

Forgotten Forest Ultra Run - Stratford, CT

Backyard Ultra Walk 2 mi
A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.
May
16
Su

Orangetheory Long Island 5K

Trail Run Walk 5 km
A 5K run/walk through Bethpage State Park featuring soft trails, live timing, free finish-line photos, and advance bib pickup at Orangetheory Fitness Farmingdale.
May
22
Sa

NSRF Long Island Lemonade Trail 5K

Trail Run Walk 5 km
A trail 5K at Blydenburgh County Park in Hauppauge with on site refreshments, an in person and a virtual participation option, and proceeds benefiting the Never Stop Running Foundation.
June 2027
Jun
12
Sa

Tough Cookie 5K

Trail Run Walk 5 km
An inaugural community 5K and 1-mile walk at Camp Edey supporting Girl Scouts programs, with race awards, family activities, and participant amenities.
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