21 Mountain Bike Trails near Overlook Mountain
first prev 1 2 next lastShowing Mountain Bike Trails within 50 miles Distance miles of Overlook Mountain Trail, Bearsville, NY 12409, USA City, Zip, or Address
Ohayo Mountain
Woodstock, New York
2.1 miles SA not-too-hard climb to the Ohayo Mountain summit near Woodstock, followed by a fast, race-it-down descent with a few steep technical sections.
Mountain Bike
Red Trail
Kingston, New York
4.8 miles SEA well-maintained network of small, technical single-track loops that rewards riders who know how to read the trail.
Mountain Bike
Wilson State Park
Mount Tremper, New York
6.0 miles SWA fun loop to goof off with near Mount Tremper — just avoid the section that floods in spring (it goes up past the handlebars).
Mountain Bike
Jockey Hill
Kingston, New York
7.0 miles SESingletrack with a little fire road near Kingston featuring bridges, a nice ridge climb, and tight rocky descents — classic Jockey Hill fun.
Mountain Bike
Round Top MTB Trails
Round Top, New York
13.5 miles NA mountain bike trail network near Round Top ranging from beginner to expert, with singletrack trails and doubletrack connector roads through the Hudson Valley hills.
Mountain Bike
The Wallkill Valley Rail Trail
Kingston, New York
13.9 miles SA scenic rail trail through a few small towns near New Paltz, New York — smooth, flat, and welcoming for beginners and kids alike.
Mountain Bike
Greenport Conservation
Hudson, New York
22.6 miles NEFlat meadow XC riding with Hudson River views transitions to twisty, rooty singletrack through the woods at Greenport Conservation in Hudson.
Mountain Bike
Spring Farm
Gardiner, New York
23.5 miles SHilly intermediate-to-advanced mountain biking at Spring Farm near Gardiner, with a rocky uphill climb, fun downhill curves, and awesome ski-loop singletrack.
Mountain Bike
Minnewaska State Park
Gardiner, New York
24.4 miles STwelve miles of carriage roads linking Lake Awosting, Castle Point, and Kempton Ledge through stunning fall foliage and sweeping views — beginner-friendly grade with great scenery payoff.
Mountain Bike
Lippman Park
Kerhonkson, New York
24.5 miles SWA trail system with raised boardwalks, skinnies, berms, and climbing near Kerhonkson, New York — easier trails at the mountain base with increasing challenge as you ascend through 17 interconnected trails.
Mountain Bike
Franny Reese State Park
Highland, New York
26.9 miles SStellar Hudson River views on singletrack trails in a centrally located Scenic Hudson park, ideal for a quick pre- or post-work ride with easy connections to rail trails and the Walkway Over the Hudson.
Mountain Bike
Taconic-hereford
Pleasant Valley, New York
29.4 miles SERolling hardwood hills and fire roads with challenging singletrack spurs near Pleasant Valley — fast and smooth to technical, roots and loose rocks throughout.
Mountain Bike
Vassar Farms
Poughkeepsie, New York
29.5 miles SEA convenient, flowing trail system just minutes from downtown Poughkeepsie — mostly smooth with short technical sections, great for quick after-work laps or cyclocross riders.
Mountain Bike
Beebe Hill
Chatham, New York
38.0 miles NEThree trails of interest in a forested area, ranging from a serene pond out-and-back to an expert fire-tower climb to a technical white diamond singletrack loop.
Mountain Bike
Harvey Mountain Trail
Austerlitz, New York
39.1 miles NEA short out-and-back ride through the woods that opens into a large blueberry field before climbing to Harvey Mountain and the New York/Massachusetts state line.
Mountain Bike
Beacon Mt.
Beacon, New York
40.7 miles SClimb blue or white singletrack (or fire road) to an old casino and fire tower, then enjoy nothing but fast downhill in every direction from the summit.
Mountain Bike
Camp Orange
Middletown, New York
40.7 miles SA flowy combination of horse trails and singletrack in Middletown, NY with long downhill rewards after uphills, log overs, stone walls, and easy suburban access.
Mountain Bike
Stewart State Forest
Rock Tavern, New York
41.4 miles SA huge 10-mile-diameter trail network of beginner-to-expert singletrack at Stewart State Forest near Rock Tavern — best explored with a local riding group for the first few visits.
Mountain Bike
Mohawk Mountain State Park
Cornwall, Connecticut
45.2 miles EA 15-mile backcountry route of logging roads and singletrack climbing to the top of Mohawk Mountain, with trail junctions, river sections, and cross-country ski terrain.
Cross-country Ski, Hike, Mountain Bike
Ninham
Carmel Hamlet, New York
47.7 miles SEVast, unmapped trail network with extremely technical terrain, no clear route, and one brutal climb — an adventurous but challenging ride for experienced MTBers.
Mountain Bike
