Black Bear Cottage / Local Guide

Into the Woods

Hiking the woods around Livingston Manor

Rail-trail strolls, wild-forest loops, and fire towers with 360° views — all within half an hour of Main Street.

The woods aren't a drive from Livingston Manor — they're the setting it sits in. Trails here range from flat rail-bed strolls to fire-tower climbs with hundred-mile views, and in a weekend you can sample all of it.

The O&W Rail Trail near Livingston Manor
The O&W Rail Trail follows the old railway bed through the valley.

Start flat

The O&W Rail Trail

The old Ontario & Western railway bed is now a walking and biking trail through the valley — flat, shaded, and good for every fitness level (it borders our own backyard, which is exactly as convenient as it sounds). It's the easiest way to be deep in the green ten minutes after you decide to be.

Covered Bridge Park

A short hop from the village, this county park preserves a 19th-century covered bridge over the Willowemoc — swimming-hole energy in summer, postcard in fall, and a fine picnic stop any time.

Go deeper

Willowemoc Wild Forest

More than 40 miles of marked trails start just outside town. The Frick Pond loop is the gentle classic; stretch it toward Hodge Pond for a roughly 6.6-mile loop through forest and wetland that feels much further from civilization than it is.

Fire towers: Balsam Lake Mountain & Red Hill

Two of the Catskills' historic fire towers stand within about 30 minutes of town. Both hikes are moderate, and both end the same way: you climb the tower stairs above the treeline and the entire Catskill range unrolls in 360 degrees. On a clear October day it's one of the best views in New York State.

Beer Mountain at Upward Brewing

The rare trailhead with a taproom at the bottom: a short forest climb on Upward's 120-acre property to a 1,870-foot overlook, then back down for a pint you've legitimately earned.

By season

Spring brings wildflowers and rushing water; summer is firefly-and-swimming-hole territory; foliage peaks in early-to-mid October and turns every trail gold; winter empties the woods entirely — bring microspikes for the fire towers and save the afternoon for sledding.

Staying nearby?

Black Bear Cottage is a renovated 1902 home on three wooded acres, two miles from Main Street — hot tub, fire pit, chef's kitchen, sleeps 8. Rated 5.0 on Airbnb.

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