Smithtown
Trail Running Calendar near Smithtown 2026-2027
Explore the top trail runs near Smithtown for 2026-2027! We've gathered 34 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A six-hour timed run and relay at Belmont Lake State Park on a 2.50 mile loop, with individual and team entries, post-event food, awards, and charity support.
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.
Four-day trail event in Rocky Point, NY featuring a 10.48-mile Pine Barrens loop with eight distance options from 10 miles to 150 miles.
A 5K trail run and an accessible short run/walk on private Gemstone Farm in Wilton, CT on 10/10/2026, with farm access, post-event food and entertainment, supporting The Prospector.
Trail 5K at Blydenburgh County Park on October 11, 2026 offering in person and virtual options, participant tees, refreshments, and age group recognition.
Multi day running weekend in Bay Shore, NY with marathon, half marathon, 10K, 5K, kids 1K, relay and a virtual 26.2 miles challenge.
Outrun the Stigma 5K Run/Walk in Massapequa Park NY features a 3.1 mile mixed surface course, kids fun run, and finisher medals for adult 5K finishers.
November 2026
A community 5K and untimed fun run at Sachem North High School on November 7, 2026, offering awards, free finish photos, and guaranteed shirts for early 5K registrants.
A community 5K at Belmont Lake State Park on November 8, 2026 offering an in-person 5K, virtual option, and a free kiddie dash with post-race refreshments.
An 8K USATF cross-country championship for Open, Masters and Para Athletic divisions at Bethpage State Park on November 8, 2026, for athletes aged 18 and older.
Trail 5K at Bethpage State Park on November 14, 2026 with in person and virtual options, a free Kiddie Dash, family amenities and postrace refreshments.
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.
Backyard Ultra at Cranbury Park in Norwalk, CT where runners repeat a precise 4.167 mile loop every hour until only one runner remains.
Inaugural Estella's Memorial 5K in Yaphank is a fundraiser for the Lustgarten Foundation held on a flat loop trail at the Suffolk County Farm and Education Center.
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.
Thanksgiving Day 5K and family 1/2 mile fun run at John J Burns Park in Massapequa with certified course, awards, post race snacks, and charity proceeds.
A community 5K trail run at Bethpage State Park on November 28, 2026, with in person and virtual options, a free kiddie fun run, bib mailing, shirts, and postrace refreshments.
Trail 5K at Belmont Lake State Park on November 29, 2026 with a cash raffle where 50% of net proceeds are awarded to present participants.
December 2026
A backyard ultra at Blydenburgh County Park: runners repeat a 4.167 mile loop each hour until one completes the final loop; proceeds support Long Island trail maintenance.