One Of The Best Small Towns In The Catskills Is A Mountain Hollow With Winding Trails And Rustic Lodges

In the early days of the 18th century, there was a man of mythic repute who roamed the Hudson River Valley. He was known as Win-ni-sook (sometimes Winneesook, believed to mean "snowfall") in his native Algonquian tongue, but many simply referred to him as the "Big Indian." At seven feet tall, as the stories go, and strong as one of hemlock trees rooted into the hillsides, Win-ni-sook was as fearsome as his reputation — and appearance — suggested. He waged war with tribal chieftains and plundered the settlements of Dutch colonists as though conflict were a sport.

But even the most imposing of men can't shirk a bullet to the heart. When Win-ni-sook was shot during one of his pillaging campaigns, he mustered up the strength to take shelter in a hollow pine tree, which soon became his final resting place. Now, 300 years later, a small hamlet sits in the valley where Win-ni-sook once marauded. And in honor of the man himself, it goes by the name of Big Indian. Win-ni-sook might have been a pugilistic character, but the bucolic town that bears his name couldn't be any different.

The Catskills hide lots of interesting settlements within their creases and valleys. There's Hobart, a charming village dedicated to book lovers, and abutting the Hudson River, Saugerites, one of America's coolest small towns. But for sheer rustic mountain charm, few can compete with Big Indian.

Unlike Win-ni-sook, Big Indian is small. Technically, it's one of 12 hamlets within Shandaken township, which itself has a total population of less than 3,000. As with many Catskill settlements, Big Indian is thoroughly scenic, with its forest-shrouded roads and leafy hiking trails (both at peak pretty in fall), and views of the rolling Catskill Mountains at every turn. You'll also find a towering, wood-carved likeness of Win-ni-sook in Big Indian Park in the heart of the hamlet, which is a good place to kick off your travels.

Hiking trails crisscross the town, traversing the 33,500-acre Big Indian Wilderness Area. Among its 30 miles of trails is the longest stretch through uninterrupted virgin forest in the entire Catskill range. Connecting eight prominent summits, including Eagle Mountain, and awash in hemlock trees, as well as northern hardwoods like American beech, sugar maple, and yellow birch, the trails form arguably the finest hiking environment in New York State. Throughout the year, you'll catch sight of many species of birds here, as well as bears, deer, bobcats, porcupines, and weasel-like fishers.

For a beginner hike, try the 1.9-mile McKinley Hollow Trail, which starts four miles south of Big Indian. Though short, it becomes progressively steeper as you ascend. For a lengthier expedition, consider the 14-mile Pine Hill-West Branch Trail, following a ridge line across five peaks. The northern trailhead is in Shandaken near Pine Hill hamlet. Another of the most popular Catskill trails is the 6.4-mile, pine-fringed Giant Ledge and Panther Mountain route. The Giant Ledge Trailhead is about 10 minutes south of Big Indian by car.

If you want to fully embrace the mountain way of life when visiting Big Indian, then you should stay in a rustic lodge. The Urban Cowboy Lodge in the Big Indian Wilderness may have a parochial name, but in design it's decidedly boutique. The 200-acre property has 44 rooms, furnished with rough-hewn woods, teepee-esque drapery, and handsome features like hand-crafted lighting fixtures and clawfoot copper tubs. It's a wonderful place to retire to after a lengthy jaunt through the hills.

There are other nice properties nearby, such as Eastwind in Oliverea Valley. The 26-room hotel sits on a lush mountainside and has been designed in a Scandi-chic style, characterized by a less-is-more philosophy, harnessing light and space to create a calming aesthetic. Equally calming is the hotel's Dandelion bar and restaurant, specializing in "forage to fork" dining and craft cocktails. Other cozy options include the Pine Hill Arms, the Shandaken Inn, and River Run Bed & Breakfast, all of which offer good access to the trails around Big Indian.

Big Indian is about two and a half hours from Manhattan. An easier (less trafficked) route might be to travel from Syracuse or Albany, both of which have airports. Syracuse, one of the most affordable cities in America for a vacation, is about three hours away by car. Albany, a 90-minute drive north along the Hudson River, is even closer.