Guidebook for Windham
Food Scene
Great for breakfast, lunch, coffee, and WiFi. Has a friendly resident pit bull.
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Higher Grounds
61 NY-296Great for breakfast, lunch, coffee, and WiFi. Has a friendly resident pit bull.
Very popular for breakfast (served all day), lunch, fresh-baked organic breads and baked goods (voted “best pies” by Hudson Valley Magazine), locally made honey, maple syrup, jams, jellies, soaps, and gifts.
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Catskill Mountain Country Store - Windham
5510 NY-23Very popular for breakfast (served all day), lunch, fresh-baked organic breads and baked goods (voted “best pies” by Hudson Valley Magazine), locally made honey, maple syrup, jams, jellies, soaps, and gifts.
A traditional diner. It has not been hipsterized. Low prices, big portions.
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Michael's Diner- Now Windham Diner
5339 NY-23A traditional diner. It has not been hipsterized. Low prices, big portions.
Greek and Italian cuisine. When you need dinner quickly, this is the spot. Pizza is very good and is made in whatever style you like, including gluten free
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Neapolis
5330 NY-23Greek and Italian cuisine. When you need dinner quickly, this is the spot. Pizza is very good and is made in whatever style you like, including gluten free
Wood-fired pizza, intimate Italian fare, and well-appointed premium wine menu.
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Millrock Restaurant
5398 NY-23Wood-fired pizza, intimate Italian fare, and well-appointed premium wine menu.
The food might be average, but the five-state view is spectacular. And for those who appreciate haunted places, it is probably the most famous one in the Catskills.
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Captain's Inn Point Lookout
7604 NY-23The food might be average, but the five-state view is spectacular. And for those who appreciate haunted places, it is probably the most famous one in the Catskills.
We don’t know quite how to describe the Chicken Run experience. It is the most popular family restaurant around, and where the locals and tourists mingle. Low prices, big portions. If you need grill and fryer food and a big bar, the Chicken Run has you covered. Some say they make the best steaks. Adults like the live music, kids love the ice cream bar, and they offer free movie screenings and s’mores at the firepit in summer.
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Chicken Run Family Restaurant and Steak House
5639 NY-23We don’t know quite how to describe the Chicken Run experience. It is the most popular family restaurant around, and where the locals and tourists mingle. Low prices, big portions. If you need grill and fryer food and a big bar, the Chicken Run has you covered. Some say they make the best steaks. Adults like the live music, kids love the ice cream bar, and they offer free movie screenings and s’mores at the firepit in summer.
Classic steak house. Quality depends on who is cooking. Not for the health conscious.
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Prime
5335 NY-23Classic steak house. Quality depends on who is cooking. Not for the health conscious.
French cuisine, lovely ambience, pet friendly, nice views from the porch dining area. If you are from New York City, this place will be familiar. Voted "Best of Hudson Valley” more than once. If you like huge portions, don’t go.
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Bistro Brie & Bordeaux
5386 NY-23French cuisine, lovely ambience, pet friendly, nice views from the porch dining area. If you are from New York City, this place will be familiar. Voted "Best of Hudson Valley” more than once. If you like huge portions, don’t go.
They take a pretty decent shot at Tex Mex. Dollar Taco Night (Thursdays) is very popular.
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Rock'n Mexicana Cantina & Grille
5220 NY-23They take a pretty decent shot at Tex Mex. Dollar Taco Night (Thursdays) is very popular.
Extremely popular, well-known restaurant owned by Southern Italy born-and-raised chef Louis Caracciolo. You may be a bit disappointed if you are used to big-city gourmet, but it is very good for most dishes.
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Brandywine
11157 NY-23Extremely popular, well-known restaurant owned by Southern Italy born-and-raised chef Louis Caracciolo. You may be a bit disappointed if you are used to big-city gourmet, but it is very good for most dishes.
When it comes to wine, specialty beers, and small plates, these folks know what they are doing. Their cheese plates and charcuterie boards feature local artisanal cheeses, salamis, and homemade pâtés. Charming vintage-boho-meets-modern ambience. A great place for lunch or before dinner.
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Ze Windham Wine Bar
5369 Main StreetWhen it comes to wine, specialty beers, and small plates, these folks know what they are doing. Their cheese plates and charcuterie boards feature local artisanal cheeses, salamis, and homemade pâtés. Charming vintage-boho-meets-modern ambience. A great place for lunch or before dinner.
Just down the road from the house, this family owned micro-winery produces small batches of hand-crafted wines and is open for tastings, sales, and parties. Enjoy their platter of regional cheeses, or pick up a lunch hamper at Todaro’s Salumeria for a special lunch on the tasting deck with a matching flight of wines. Open year round but hours vary, so check the website.
Windham Vineyard & Winery
11 Mountain View EstatesJust down the road from the house, this family owned micro-winery produces small batches of hand-crafted wines and is open for tastings, sales, and parties. Enjoy their platter of regional cheeses, or pick up a lunch hamper at Todaro’s Salumeria for a special lunch on the tasting deck with a matching flight of wines. Open year round but hours vary, so check the website.
Drinks & Nightlife
Jimmy OConnors Windham Mt. Inn
141 South StFriendly local establishment
Home brew and pub food. They are doing it right. If you like the beer, grab a growler from atop our kitchen cabinets and get a fill up ($15) for home.
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Cave Mountain Brewing Company
5359 New York 23Home brew and pub food. They are doing it right. If you like the beer, grab a growler from atop our kitchen cabinets and get a fill up ($15) for home.
Shopping
Grocery store is small with a very limited selection, but most anything you need for Italian cooking, and an excellent Italian deli and bakery with fresh-baked breads, regional cheeses, meats, olives, and more. Excellent sandwiches, salads, and more at the deli. Takeaway only.
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Todaro's Salumeria
5344 NY-23Grocery store is small with a very limited selection, but most anything you need for Italian cooking, and an excellent Italian deli and bakery with fresh-baked breads, regional cheeses, meats, olives, and more. Excellent sandwiches, salads, and more at the deli. Takeaway only.
Parks & Nature
A very easy and friendly hiking or jogging course, and right in town so you can leave the bear spray at home!
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The Windham Path
4982 NY-23A very easy and friendly hiking or jogging course, and right in town so you can leave the bear spray at home!
This 260-foot waterfall, the highest in NY State, has been one of the region’s most popular destinations for centuries and has captivated the hearts, pens and paintbrushes of poets, painters, film makers, from Washington Irving’s Rip Van Winkle, to Asher Durand’s Kindred Spirits and William Cullen Bryant’s romantic verse. The falls are surrounded by hiking trails, and you can climb high enough to view the Hudson River Valley and parts of Vermont, Massachusetts, and Connecticut. Stay on the path and exercise caution. See HiketheHudsonValley.com for directions.
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Kaaterskill Falls
This 260-foot waterfall, the highest in NY State, has been one of the region’s most popular destinations for centuries and has captivated the hearts, pens and paintbrushes of poets, painters, film makers, from Washington Irving’s Rip Van Winkle, to Asher Durand’s Kindred Spirits and William Cullen Bryant’s romantic verse. The falls are surrounded by hiking trails, and you can climb high enough to view the Hudson River Valley and parts of Vermont, Massachusetts, and Connecticut. Stay on the path and exercise caution. See HiketheHudsonValley.com for directions.