Guidebook for Windham Area
Parks & Nature
Excellent place for a walk, run or bike ride. The main loop takes about 30 minutes to walk. Along the way, you'll see open meadows, a flowing stream and maybe even a beaver dam. Definitely accessible in winter when the snow is not too heavy. Parking lot onsite, and often a portable restroom during the summer.
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The Windham Path
4982 NY-23Excellent place for a walk, run or bike ride. The main loop takes about 30 minutes to walk. Along the way, you'll see open meadows, a flowing stream and maybe even a beaver dam. Definitely accessible in winter when the snow is not too heavy. Parking lot onsite, and often a portable restroom during the summer.
Moderate/Difficult hiking trail a few minutes from the condo. Takes 3+ hours round trip. Nice views from the top.
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Windham High Peak
Moderate/Difficult hiking trail a few minutes from the condo. Takes 3+ hours round trip. Nice views from the top.
One of New York's grandest waterfalls. If you want to hike, park just above the falls. The trail takes you along the river to the base of the falls. If you want an easier walk, drive to the parking lot off Laurel House Road, and there's a viewing platform. Research this online, and you'll see what we mean. :-)
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Kaaterskill Falls
One of New York's grandest waterfalls. If you want to hike, park just above the falls. The trail takes you along the river to the base of the falls. If you want an easier walk, drive to the parking lot off Laurel House Road, and there's a viewing platform. Research this online, and you'll see what we mean. :-)
Food Scene
Reliable food, great bar. Specializes in families and large groups. Outdoor activities to keep kids entertained.
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Chicken Run Family Restaurant and Steak House
5639 NY-23Reliable food, great bar. Specializes in families and large groups. Outdoor activities to keep kids entertained.
Most reliable breakfast and lunch spot in town. Always good food at good prices. ONLY TAKES CASH, so hit the ATM before going.
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Michael's Diner- Now Windham Diner
5339 NY-23Most reliable breakfast and lunch spot in town. Always good food at good prices. ONLY TAKES CASH, so hit the ATM before going.
Coolest ambiance in town. Old bank building. You can actually sit in the remnants of the vault! Best for breakfast and lunch.
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The Windham Local
5410 NY-23Coolest ambiance in town. Old bank building. You can actually sit in the remnants of the vault! Best for breakfast and lunch.
Closest restaurant to the condo. Open for dinner only, and the bar is sometimes open as late as 11pm on Fridays and Saturdays. Simple menu.
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Zack's Place
383 NY-296Closest restaurant to the condo. Open for dinner only, and the bar is sometimes open as late as 11pm on Fridays and Saturdays. Simple menu.
Great place for breakfast. Sit outside if it's a nice day. Can smell a little grease-trappy inside.
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Nana Gail's
387 NY-296Great place for breakfast. Sit outside if it's a nice day. Can smell a little grease-trappy inside.
Great place for fine dining. Can be a little pricey, but a beautiful place with a great bar.
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Prime
5335 NY-23Great place for fine dining. Can be a little pricey, but a beautiful place with a great bar.
Best view of any restaurant in the area. Feels a bit formal when you walk in, but it's actually very casual. Never had a bad meal here. Captain Wayne is often there. Former Merchant Marine whose dream was to open a restaurant. Great host. GREAT happy hour from 3-5pm.
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Captain's Inn Point Lookout
7604 NY-23Best view of any restaurant in the area. Feels a bit formal when you walk in, but it's actually very casual. Never had a bad meal here. Captain Wayne is often there. Former Merchant Marine whose dream was to open a restaurant. Great host. GREAT happy hour from 3-5pm.
Some find the decor a bit dated, but we feel this is the best food in Windham. We find their steaks to be even better than at Prime, an actual steakhouse! If you like lotto, you can play QuickDraw at the bar. :-)
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Messina's Lagriglia Ristorante
5658 NY-23Some find the decor a bit dated, but we feel this is the best food in Windham. We find their steaks to be even better than at Prime, an actual steakhouse! If you like lotto, you can play QuickDraw at the bar. :-)
Neapolis
5330 NY-23Drinks & Nightlife
Hands down, most favorite spot in town for a nice evening. They serve wine and beer, but not liquor. Say Mike and Chris sent you. :-)
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Ze Windham Wine Bar
5369 Main StreetHands down, most favorite spot in town for a nice evening. They serve wine and beer, but not liquor. Say Mike and Chris sent you. :-)
West Kill Brewing
2173 Spruceton RdA real gem. Excellent beer and a very cool tasting room.
Most spacious bar in Windham. Good rotating beer selection with local drafts. Food is basic but reliable. Plenty of TV's, and they might let you see the speakeasy if you so nicely. They also have table seating.
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Tap House Grille
5359 NY-23Most spacious bar in Windham. Good rotating beer selection with local drafts. Food is basic but reliable. Plenty of TV's, and they might let you see the speakeasy if you so nicely. They also have table seating.
Arts & Culture
Windham Fine Arts
5380 NY-23Getting Around
Closest Amtrak stop to Windham. Roughly a 45-minute drive from Windham.
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Hudson
69 S Front StClosest Amtrak stop to Windham. Roughly a 45-minute drive from Windham.
Sightseeing
The local ski mountain. Often festivals in the summer. Beautiful views if the skyride is open.
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Windham Mountain Resort
19 Resort DrThe local ski mountain. Often festivals in the summer. Beautiful views if the skyride is open.
Shopping
Tiger Lily Jeweler
5348 NY-23Great local jewelry shop.
Not too much local merchandise, but a good place if you need to pick up a simple gift.
Carole's Gift Emporium
5338 NY-23Not too much local merchandise, but a good place if you need to pick up a simple gift.
Mostly a pharmacy, but has an EXCELLENT home goods and gift section. If you need a greeting card, this is the place to go.
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Windham Pharmacy
61 ST NY-296Mostly a pharmacy, but has an EXCELLENT home goods and gift section. If you need a greeting card, this is the place to go.
THE best gift shop in the area. Beautiful crafts and a number of kid-friendly options. Totally worth browsing even if you don't really need anything!
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European Craft Store
6 Mill StTHE best gift shop in the area. Beautiful crafts and a number of kid-friendly options. Totally worth browsing even if you don't really need anything!