Mountaintop Chalet Guidebook

Carolyn+Dan
Mountaintop Chalet Guidebook

City/town information

Nestled into the mountains of the northern Catskill Mountains, Windham NY brings together the best of the region - natural beauty and outdoor adventures. The pristine and quaint downtown is the heart of the historic mountaintop resort town.
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Windham
164 vendasit rekomandojnë
Nestled into the mountains of the northern Catskill Mountains, Windham NY brings together the best of the region - natural beauty and outdoor adventures. The pristine and quaint downtown is the heart of the historic mountaintop resort town.

Food scene

THIS IS OUR FAV!!! Fellow is the place for coffee, tasty baked goods, excellent egg sammies and THE CINNAMON ROLLS!! We usually go here for breakfast or lunch (sometimes both) almost every weekend.
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Fellow Mountain Cafe
7883 Main St
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THIS IS OUR FAV!!! Fellow is the place for coffee, tasty baked goods, excellent egg sammies and THE CINNAMON ROLLS!! We usually go here for breakfast or lunch (sometimes both) almost every weekend.
This is one of our favorite places for dinner. The vibe, the setting and the menu all make this place a true gem. Prospect restaurant and bar serves a playful twist on local cuisine inspired by the rich and diverse offerings of the Hudson Valley. Their dining room has floor to ceiling windows, mountain views and a large circular bar with cast-iron stoves. Just off the bar is a large deck featuring seasonal outdoor dining and a fire pit.
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The Prospect
13 Scribner Hollow Rd
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This is one of our favorite places for dinner. The vibe, the setting and the menu all make this place a true gem. Prospect restaurant and bar serves a playful twist on local cuisine inspired by the rich and diverse offerings of the Hudson Valley. Their dining room has floor to ceiling windows, mountain views and a large circular bar with cast-iron stoves. Just off the bar is a large deck featuring seasonal outdoor dining and a fire pit.
Our newest addition to Windham, Babbler's Cafe at Wylder Hotel is great place to grab coffee, baked goods or a sandwich. It is a cute, laid-back place right along the river. The full restaurant is due to open soon (Aug 2022).
Wylder Hotel Windham
19 New York 296
Our newest addition to Windham, Babbler's Cafe at Wylder Hotel is great place to grab coffee, baked goods or a sandwich. It is a cute, laid-back place right along the river. The full restaurant is due to open soon (Aug 2022).
Just 5 min up the road from the Chalet, this is the place to sample Riesling, merlot, and cabernet franc from the vineyard, alongside a larger selection of wines from the Finger Lakes, Hudson Valley, and Long Island regions, in a scenic winery setting where the rows of vines disappear into the greenery of the mountain backdrop.
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The Vineyard at Windham
11 Mt View Estates Rd
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Just 5 min up the road from the Chalet, this is the place to sample Riesling, merlot, and cabernet franc from the vineyard, alongside a larger selection of wines from the Finger Lakes, Hudson Valley, and Long Island regions, in a scenic winery setting where the rows of vines disappear into the greenery of the mountain backdrop.
Sealed with the local stamp of approval, the cozy cafe specializes in wine, charcuterie, and cheese boards. The area’s only accredited sommelier has curated a list of over 40 by-the-glass wines, alongside a selection of German beers. Take a lesson in vino and food pairings at the weekly wine school, or enjoy summer evenings in the beer garden.
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Ze Windham Wine Bar
5369 Main Street
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Sealed with the local stamp of approval, the cozy cafe specializes in wine, charcuterie, and cheese boards. The area’s only accredited sommelier has curated a list of over 40 by-the-glass wines, alongside a selection of German beers. Take a lesson in vino and food pairings at the weekly wine school, or enjoy summer evenings in the beer garden.
We love this place. It is just 8 min from the Chalet and a great place for breakfast and lunch. On the weekends they serve dinner and host live music.
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The Windham Local
5410 NY-23
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We love this place. It is just 8 min from the Chalet and a great place for breakfast and lunch. On the weekends they serve dinner and host live music.
Great place for coffee, smoothies and yummy treats.
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Higher Grounds
61 NY-296
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Great place for coffee, smoothies and yummy treats.
Cider donuts, honey sticks, boardgames, pancake breakfast, goats and bunnies.... The Country Store is a great place to bring the family for the quintessential country store vibe. And its just down the road from the Chalet.
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Catskill Mountain Country Store - Windham
5510 NY-23
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Cider donuts, honey sticks, boardgames, pancake breakfast, goats and bunnies.... The Country Store is a great place to bring the family for the quintessential country store vibe. And its just down the road from the Chalet.
This great Italian place right in downtown. In our opinion, this is the best pizza in town. In addition to the main dining room in the front, they recently added a new bar and patio area in the back. Mark, the main bartender, is super friendly and very talented!
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Millrock Restaurant
5398 NY-23
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This great Italian place right in downtown. In our opinion, this is the best pizza in town. In addition to the main dining room in the front, they recently added a new bar and patio area in the back. Mark, the main bartender, is super friendly and very talented!
The parking lot speaks for itself... in that it is always full. This is the go-to with kids for yummy food and a fun outdoor area in the warmer months.
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Chicken Run Family Restaurant and Steak House
5639 NY-23
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The parking lot speaks for itself... in that it is always full. This is the go-to with kids for yummy food and a fun outdoor area in the warmer months.
Solid place for yummy, filling food right in town.
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Lilly's Steaks & Cocktails
5335 New York 23
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Solid place for yummy, filling food right in town.
This is one of our favorite restaurants in the area!!! The restaurant at the Deer Mountain Inn is a community living room – a place for locals, weekenders, and visitors to meet, greet, and eat. Our comfortable dining room welcomes all, whether for a small plate and drink on the mountain-view patio, a leisurely three-course meal near the cozy fireplace, or dessert and a digestif at our full-service bar, which offers classic spirits, hand-crafted cocktails, a smart wine list, and local brews.
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Deer Mountain Inn
790 Co Rd 25
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This is one of our favorite restaurants in the area!!! The restaurant at the Deer Mountain Inn is a community living room – a place for locals, weekenders, and visitors to meet, greet, and eat. Our comfortable dining room welcomes all, whether for a small plate and drink on the mountain-view patio, a leisurely three-course meal near the cozy fireplace, or dessert and a digestif at our full-service bar, which offers classic spirits, hand-crafted cocktails, a smart wine list, and local brews.
Part of the Windham Country Club, golfers and non-golfers will find the outside patio dining area a great place to grab a meal. Its really a beautiful spot.
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Mulligan's Pub
36 South St
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Part of the Windham Country Club, golfers and non-golfers will find the outside patio dining area a great place to grab a meal. Its really a beautiful spot.
Great new diner for breakfast and lunch. Yummy food in a cozy setting.
Day June Luncheonette
Great new diner for breakfast and lunch. Yummy food in a cozy setting.
Great Mexican spot - one of our go-to's is you are looking for yummy comfort food that won't break the bank! They also have online ordering so this is one of our favorite take-out places in town.
Zicatelas 2
Great Mexican spot - one of our go-to's is you are looking for yummy comfort food that won't break the bank! They also have online ordering so this is one of our favorite take-out places in town.

Grocery Stores

A great place to provision, this little market provides a Deli, Beer Cave, and even Wood Fired Pizza. They have a pretty great selection of groceries in you need to stock up for your stay.
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Hickory Hill Market
5200 NY-23
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A great place to provision, this little market provides a Deli, Beer Cave, and even Wood Fired Pizza. They have a pretty great selection of groceries in you need to stock up for your stay.
Well-stocked grocery store up on the mountaintop.
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Tops Friendly Market
6350 Main St
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Well-stocked grocery store up on the mountaintop.
Very large grocery store with everything you could need. A great place to start before driving up to the mountaintop if coming from exit 21 off I-87
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Hannaford Supermarket
223 Main St
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Very large grocery store with everything you could need. A great place to start before driving up to the mountaintop if coming from exit 21 off I-87
Fantastic little shop with coffee, pastries, cheese, meats and provisions.
Paracasa
391 New York 296
Fantastic little shop with coffee, pastries, cheese, meats and provisions.