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Trail Running Calendar near Rosendale 2026-2027

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Explore the top trail runs near Rosendale 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.

Trail Running Calendar United States
September 2026
Sep
12
Sa

Shawangunk Ridge Trail Run (SRT)

Trail Run 13 mi 30 mi 70 mi
A trail event on the Shawangunk Ridge near Rosendale, NY offering 70 mile, 30 mile and half marathon divisions across rugged, varied terrain with minimal support.
Sep
13
Su

Barry Hopkins Run at Olana

Trail Run 4 mi
A scenic 3.8 mile cross-country run at Olana State Historic Site with a free 1K kids run and awards across age groups.
Sep
26
Sa

Cat's Tail Marathon

Trail Run 26 mi
Approximately 26 mile point to point trail race in the Slide Mountain Wilderness, summiting several Catskills High Peaks with nearly 7000 ft of elevation gain.
Sep
27
Su

Gardiner Dump Run

Trail Run 5 km 10 km
Trail-based 5K at Gardiner’s Riverbend Trails with a two-lap 10K option, a kids run, sneaker recycling, and day-of cash or check registration.
October 2026
Oct
4
Su

Rosendale Runs Half Marathon

Trail Run 4 mi 13 mi
Half marathon and 6K on the Wallkill Valley Rail Trail near Rosendale NY, with a mostly flat unpaved course and a crossing of the historic Rosendale Trestle.
Oct
11
Su

Obstacle Wonderland Hallo-Weird Adult 5k Obstacle Course Race

Obstacle Run 5 km
Pickle-themed Halloween obstacle event with an adult 5K, kids 1K, a pumpkin carry fundraiser, themed medals and mud at Obstacle Wonderland in Wallkill NY.
Oct
17
Sa

HHNC Meadows & Trails 5K

Trail Run 5 km
HHNC Meadows & Trails 5K is an off road 5K at Hudson Highlands Nature Center in Cornwall NY on 10/17/2026, featuring meadows, ponds, wooded trails and views of Black Rock Mountain. Entry is $35 and children under 18 run free.
Oct-Nov
31-1
Sa - Su

Fall Back Into The Trails Series

Trail Run 10 km 50 km 100 km
A multi-day trail running event at Red Wing Recreation Area near Lagrangeville, NY offering 100k, 50k and 10k looped courses with aid, medals and UTMB Index status.
November 2026
Nov
21
Sa

Sargent Elementary Turkey Trot 5K

Trail Run 5 km
A community 5K and a 1-mile kids run at Sargent Elementary in Beacon, NY, with a food drive, live DJ, and refreshments.
April 2027
Apr
24
Sa

Squatchywaska Mountainfest

Trail Run 10 mi 25 km
Limited-entry trail festival in Ellenville NY featuring technical 25K (≈17M) and 10M routes on the Shawangunk Ridge, with a lottery entry and support for Run Wild, Inc.
Apr
24
Sa

Sterling Squatch Half Marathon

Trail Run 10 mi 17 mi
Technical mountain trail races in Ellenville NY on April 24 2027 featuring 25K and 10 mile courses, six hour cutoffs, and a 150 runner cap supporting Run Wild, Inc.
May 2027
May
1
Sa

Rock The Ridge

Trail Run 26 mi 50 mi
A charity trail event at Mohonk Preserve featuring a 50-mile ultra, a 26.2 mile trail marathon, and relay options through the Shawangunk Mountains.
May
2
Su

Breakneck Point Trail Runs

Trail Run 15 mi 27 mi
Half and full trail races near Beacon, NY on steep, technical single-track with significant elevation change, aid stations, and enforced cutoffs.
May
16
Su

Run like the Wind 5K - Ellenville

Trail Run 5 km
A community 5K in Ellenville starting and finishing at Aroma Thyme Bistro, with a course along the base of the Shawangunk Mountains and a stretch on the newly resurfaced Rail Trail. Proceeds benefit local food pantries and youth scholarships.
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.
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