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Trail Running Calendar near Rocky Point 2026-2027

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Explore the top trail runs near Rocky Point for 2026-2027! We've gathered 26 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

April 2027
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
8
Sa

Camp Mountain Laurel Color Run & Trail Run

Road Race Trail Run 5 km
Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.
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
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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