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Trail Running Calendar near Gardiner 2026-2027

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Explore the top trail runs near Gardiner for 2026-2027! We've gathered 15 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2026
Nov
21
Sa

Sargent Elementary Turkey Trot 5K

Trail Run 5 km
A community Turkey Trot at Sargent Elementary in Beacon NY with a 5K Run Walk, a one mile kids fun run, a food drive, live DJ and refreshments.
Nov
22
Su

After the Leaves/Josh Feldt Half Marathon

Trail Run 13 mi
Trail half marathon at Minnewaska State Park Preserve around two glacial lakes and along the Shawangunk Ridge; online registration, $30 fee, 300 runner cap.
April 2027
Apr
3
Sa

Big Bear Squatch North

Trail Run 10 km 13 mi
Mountain 10K and half marathon in Bear Mountain NY on rugged technical trails with steep climbs, scrambling, and mandatory safety gear.
Apr
24
Sa

Squatchywaska Mountainfest

Trail Run 10 mi 17 mi
A technical trail festival on the Shawangunk Ridge near Ellenville NY offering a 25K (about 17 miles) and a 10 mile course with limited field size and on-course aid stations.
Apr
24
Sa

Sterling Squatch Half Marathon

Trail Run 10 mi 17 mi
Mountain trail races in Ellenville NY on April 24, 2027 offering technical 25K and 10 mile lollipop courses with limited field and a 6 hour cutoff.
May 2027
May
1
Sa

Rock The Ridge

Trail Run 26 mi 50 mi
A trail event at Mohonk Preserve offering a 50 mile ultra, a 26.2 mile marathon, and relay teams while fundraising for land protection and education programs.
May
1
Sa

Bear Mountain Trail Challenge

Trail Run 10 km Half Marathon 50 km
Trail races of 10K, half marathon and 50K on technical singletrack with rolling climbs at Bear Mountain State Park on May 1, 2027.
May
8
Sa

Breakneck Point Trail Runs

Trail Run Half Marathon 15 mi Marathon 27 mi
A technical trail race in Beacon NY with a half and full marathon featuring heavy elevation gain, exposed climbs, aid stations, and strict aid station support rules.
May
15
Sa

Millbrook Vineyards Wine Run 5k

Trail Run 5 km
A 5k and 1.5 mile walk at Millbrook Vineyards & Winery on May 15, 2027, featuring a mostly grass cross country course and a post run wine pour.
May
16
Su

Run like the Wind 5K - Ellenville

Trail Run 5 km
Scenic community 5K in Ellenville on May 16, 2027, starting and finishing at Aroma Thyme Bistro with a Rail Trail course and a garden post race gathering.
May
22
Sa

Brooklyn Cider House Spiked Apple 5K

Trail Run 5 km
A chip timed 5K at Brooklyn Cider House on May 22, 2027 combining a run or walk with local cider, a shirt, medal, donut and a pour of cider.
July 2027
Jul
14
We

Bowdoin Bushwhack

Trail Run 5 mi
A roughly 5 miles trail run through varied terrain at Bowdoin Park in Wappingers Falls, with a 150 runner cap and awards for overall top finishers.
September 2027
Sep
11
Sa

Shawangunk Ridge Trail Run (SRT)

Trail Run 13 mi 30 mi 70 mi
A trail event on the 70-mile Shawangunk Ridge near Rosendale NY offering 70, 30, and half marathon divisions on rugged unsupported terrain.
Sep
19
Su

Gardiner Dump Run

Trail Run 5 km 10 km
Trail event at Gardiner Riverbend Trails with a 5K or two lap 10K, sneaker recycling coupons, pre registration T shirts, and day of cash or check registration.
October 2027
Oct
30-31
Sa - Su

Tri-State New York Spartan Event Weekend

Obstacle Run 5 km 10 km
Obstacle course weekend at Sunflower Valley Farm on Oct 30 and 31 2027 featuring a 5 km Sprint, 10 km Super, and a kids race with obstacles.
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