Rocky Point
Trail Running Calendar near Rocky Point 2026-2027
Explore the top trail runs near Rocky Point for 2026-2027! We've gathered 30 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A family friendly, obstacle filled beach 5k in Stratford that raises funds for Sterling Community Center while supporting individual and team fundraising.
A six-hour timed run and relay at Belmont Lake State Park where individuals and teams cover as many 1.50 mile loops as possible, with awards and commemorative apparel.
October 2026
A 30 hour loop ultrarun in Roosevelt Forest CT on 2.5 mile laps offering distances to 100 miles with a finisher buckle and a single pavilion aid station.
Multi-day trail event in Rocky Point NY on a 10.48 mile loop used for distances from 10 to 150 miles, with two aid stations and crew support.
Trail 5K and free kiddie dash at Blydenburgh County Park on October 11, 2026 with a virtual option, finisher tee, shaded trails, and postrace refreshments.
Experience Long Islands scenic Robert Moses Causeway in this multi day running event. Support local veterans while choosing between marathon, half marathon, 10k, and 5k distances with finisher medals for all participants.
An off road 50K from Guilford Lakes School through rocky forest roads and single track, with aid stations, time cutoffs, and staggered entry fees.
A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.
November 2026
A community 5K at Belmont Lake State Park on November 8, 2026 with in-person and virtual options, family activities, postrace refreshments, and proceeds supporting the Never Stop Running Foundation.
A trail event in Manorville Hills with 3, 6, 12 and 24 hour options on a runnable 5K loop featuring about 270 feet gain per loop.
An inaugural backyard ultra at Cranbury Park where runners repeat a 4.167 mile loop each hour until one runner remains, with crew access and central aid near the corral.
Trail half marathon and 5 mile at Brookhaven State Park on Nov 15, 2026, on single track and fire trails with awards, cash prizes, and finisher medals.
Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.
December 2026
Timed up and back trail event at Sleeping Giant State Park with four hour and eight hour options and 3.3 mile laps to the Observation Tower.
A weekend trail event in Blydenburgh County Park featuring a Backyard Ultra with 4.167 mile hourly loops and a separate 4.16 mile lapping race. A portion of proceeds supports the Long Island Greenbelt Trail Conference.
Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.
March 2027
Timed trail races at Sunken Meadow State Park where runners repeat an approximately 1.4 mile loop; winners cover the most distance in 3 hour and 1 hour formats.
Chip timed 5k run and walk at Osprey’s Dominion Vineyards in Peconic, NY on March 20, 2027, over a two lap cross country loop with a postrace wine pour for eligible participants. Registration includes a T shirt, collapsible wine glass and finisher me..
A six hour trail ultra at Roosevelt Forest in Stratford CT on a 2.3 mile loop with roots, rocks and rolling hills; field limited to 50 participants.