Known as the “Gem of the Catskills,” Windham is known for its ski resort and incredible mountain scenery. If you are looking for an escape into the wilderness, drive through the Catskill mountains and visit this idyllic town. Each season highlights a different part of the town – Spring the returning green leaves on the mountain tops, Summer the fantastic weather to hike and swim, Fall the changing leaves blanketing the landscape, and Winter allowing the snow to take possession of the mountains.
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It doesn’t matter if the season is summer or winter, Windham Mountain has activities all year round. During the warmer months, the trails open up to mountain bikers while the colder months bring in the skiers and snowboarders as they fly down the slope. Rent equipment at the mountain or bring your own to ride down more than 10 different trails spread across the mountain.
When the cold pushes you indoors, grab a cup of hot chocolate and sit by the roaring fire. Or if you need something stronger head up the stairs and get a drink at the bar. I’ve skied there for years and the best part is the range of difficulty in lifts, so anyone can go down the hill at their own pace. This is a resort built around all ages, and continually brings in large groups of people to ski down its trails.
Windham Fine Arts
Displaying a range of contemporary art from traditional landscapes, sculptures, abstract art, prints, photography and more, the Windham Fine Arts gallery is the perfect place to spend one to two hours of your time. Housed in an 1855 building that was restored and opened in 2003, there are both local and international artists displayed across 3,000 square feet of space.
Take some time to walk through the permanent collection of art, or enjoy the varying exhibitions featured throughout the year.
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Five State Lookout
Take a few minutes to stop at this observation deck right off of Route 23, especially on a clear day. From the deck you’ll be able to see the mountain ranges of five states. There are the White Mountains of New Hampshire, the Green Mountains of Vermont, the Berkshire Mountains of Massachusetts, the Helderberg Mountains of New York, and the Connecticut Valley all within your view.
Not many states have the opportunity to see several others while still standing in that state, but New York advantageously is located right next to several states, and they seem to all coalesce in this one location. You can visit this place all year, depending on what you want to see. The Fall foliage is sure to be stunning, or maybe you want a sea of green to take a picture of, or watch as the color fades into white as the snow takes over.
Briars and Brambles Books
Carrying a selection of both the classics and recently released novels, Briars and Brambles is the “go-to Indie bookstore in the heart of the Catskill Mountains.” Along with paperback books, they also provide audiobook subscriptions, so you can listen to your favorites while driving or working.
Look up their website to see what special events are coming up, what the staff are reading and recommend, and the staff’s backgrounds. You will find the book for you in these shelves, and if you want to stay for a little while, there is a fireplace in the middle of the store, complete with a couple of chairs to relax and get lost in your new book.
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Windham Vineyard & Winery
Using their four acres of land to their advantage, the Windham Vineyard crafts delicious wines while sourcing selections from across New York State. Try their house wines – “Aphrodite” Rosé, Diamond Sparkling, Dry Riesling, or The Bootlegger – or try wine from the Finger Lakes or Long Island.
Head into the tasting room by yourself or with friends and try one of their several tasting packages, where you can have great wine and even better conversations. If you’re looking for food to pair with the wine, don’t worry as they also provide charcuterie boards at an extra cost. This is the perfect place to let loose, and immerse yourself in the beauty of the Catskill Mountains.
The Chicken Run
Located right at the bottom of Windham Mountain, the Chicken Run is a sprawling rustic restaurant that aims to serve comfort food that’ll keep you coming back for more. Along with outdoor and indoor seating, this restaurant welcomes local bands to play Thursday through Saturday night, drawing big crowds while they play in the bar area or the stage outside.
- Hours: Tues & Wed 4-8:30, Thurs 12-8:30, Fri & Sat 12-9, Sun 12-8
- Featured Food: The Chicken Run Combo / Famous Grilled Sausage
The Windham Diner
Right on Main Street, the Windham Diner is open all day, so you can go to breakfast, lunch, or dinner at this small establishment. Choose from a large variety of options and get your food quickly, with servers that constantly check up on how you are doing. If you like diners, then this is the place to go, especially since all of their food is quite delicious.
- Hours: Mon-Sun 8-8
- Featured Food: Stuffed Shrimp / Chicken Primavera
This town is hidden in the Catskills, but is definitely a place to stop and look around. Take in the upstate New York air, enjoy the nature, and have some great food.