Chestertown is a very small town in the Adirondacks, and you might not expect it to be a particularly exciting destination at first look. But if you dig a little deeper, you’ll find that a surprising number of hidden gems surround this upstate hamlet. Good eats, beautiful hikes, and popular winery are just a few of the perks of the Chestertown area, which is an easy 80-mile drive north from Albany. Sounds like the perfect weekend trip.
The charming Friends Lake Inn is the ideal mountain escape, complete with easy access to Friends Lake, fantastic dining, luxurious rooms, kayak rentals, and more. It's also only a half-hour drive from lake George.
Mike and Sasha Pardy opened Adirondack Winery in 2008 as one of the first micro-wineries nationwide. Book a wine tasting session and try a few of this winery's more than 30 hand-crafted wines.
Ten minutes down the road from Friends Lake Inn is Lazy Moose Garden Market, a general store, greenhouse, and deli all in one destination. Spend the morning sipping on coffee, exploring the gorgeous greenhouse and enjoying one of the coolest general stores in the region.
There are 11 different trails and mountain hikes that make up the Chester Challenge, which includes dozens of miles of great trails from Stewart Mountain to Chester Creek. The challenge was initially awarded to the town by the Glen Falls Hospital's Health Promotion Center to promote physical fitness.
The Bullhouse, a steak and seafood restaurant in Chestertown, has one of the most mouth-watering menus you'll find in upstate New York. From bacon-wrapped dates to a New York Strip, you'll hope this meal never ends.
If you're looking for a prime campsite in the area, Riverside Pines is great option and has its own camp store on the grounds for campers' convenience. It's got everything from boat rentals to tennis courts to a snack bar, not to mention some of the most beautiful lakeside views in the region.
Dynamite Hill Recreational Area offers all the outdoor activities one could hope for on an Adirondack exploration. Hiking and cycling are very popular, but it's also a great spot for winter sports, including skiing, ice skating and snowshoeing.
Another perk of this underrated Adirondack town is its proximity to Mt. Macy, the tallest point in New York at 5,344 feet. It’s more than an hour drive from Chestertown, but if you’re up for an adventure, the views are certainly worth it.
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