Windham

Windham draws weekenders with ski runs on Windham Mountain and quick access to the Elm Ridge trail network. Compact, walkable Main Street hosts everything from ski shops to surprisingly serious restaurants.

Field Guides
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Main Street Eats In Windham

Grab wood-fired pizza or house-made pasta around Main Street; settle into evening with local brews or cozy eats after the slopes.

Chicken Run Family Restaurant and Steak House

🔥

Chicken Run Family Restaurant and Steak House

$

$$

Windham

4.4
Millrock Restaurant & Bar Room

🔥

Millrock Restaurant & Bar Room

$

$$

Windham

4.6
Prominence Restaurant

🔥

Prominence Restaurant

$

$$$

Windham

4.7
Albergo Breakfast Restaurant

🔥

Albergo Breakfast Restaurant

$

$$

Windham

5.0
Windham Pizzeria

🔥

Windham Pizzeria

$

$$

Windham

4.4
Brandywine

🔥

Brandywine

$

$$

Windham

4.4

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Après-Ski, Catskills Style

Post-run, bars and taverns tilt toward local taps and live music sets—expect crowds at Windham Mountain lodges and corner spots.

Taphouse Grille Windham

🔥

Taphouse Grille Windham

$

$$

Windham

4.2
The Tipp Tavern

🔥

The Tipp Tavern

$

$$

Windham

4.0
Jimmy O’Connor’s Windham Mtn. Inn

🔥

Jimmy O’Connor’s Windham Mtn. Inn

$

$$

Windham

4.4

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Value
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Neighborhood

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Chicken Run Family Restaurant and Steak House

Chicken Run Family Restaurant and Steak House

$$

Restaurant

No items found.

Windham

Restaurant
Bar
4.4
Families and locals stream in for fried chicken, live music, and plenty of laughter. Platters arrive hot, popcorn is scattered around the tables.
The Haus Windham

The Haus Windham

$$$

Lodging

No items found.

Windham

Lodging
4.7
Glass cabins, private hot tubs, and Catskill forest all around. Mornings here start clear and slow, with wind through the pines and steam rising.
The Henson

The Henson

$$$

Lodging

No items found.

Windham

Lodging
Spas & Retreats
Restaurant
Bar
4.9
A 200-year-old inn, reimagined with care and fresh perspective. Sun-drenched breakfasts, garden views, and the hum of happy guests.
Brandywine

Brandywine

$$

Restaurant

🍝 Italian

🦞 Seafood

🥩 Steakhouse

Windham

Restaurant
Bar
4.4
Long-running Italian spot where the wood paneling sets the mood. Plates of veal, pasta, and old-school desserts hold down the menu.
Antique Rose Inn

Antique Rose Inn

$$

Lodging

No items found.

Windham

Lodging
4.9
Turn-of-the-century inn where hosts greet guests with hot pancakes and Catskills history. Porch breakfasts linger, mountains crowd in the background.
Millrock Restaurant & Bar Room

Millrock Restaurant & Bar Room

$$

Restaurant

No items found.

Windham

Restaurant
Bar
4.6
Classic Italian plates and good whiskey pour from the bar room, both humming most nights. Wood-fired pizzas, eggplant, and live music linger after dark.
Hayfield

Hayfield

Wedding Venue

No items found.

Windham

Wedding Venue
4.8
A storied 19th-century barn sits among meadow and sky at the edge of Maplecrest. Strings of lights, old trees, and pure Catskills spirit greet every guest.
Taphouse Grille Windham

Taphouse Grille Windham

$$

Bar

No items found.

Windham

Bar
Restaurant
4.2
Classic bar and grill that feels tied to the heart of Windham. Plates hit the table with burgers, wings, and a draft list that holds its own.
The Tipp Tavern

The Tipp Tavern

$$

Bar

No items found.

Windham

Bar
Restaurant
4.0
A straightforward Irish pub with a lived-in Catskills feel. Hand-pulled pints, hearty fare, and a room buzzing with darts and pool.
Skin Concept Esthetics and Wellness SPA

Skin Concept Esthetics and Wellness SPA

$$

Spas & Retreats

No items found.

Windham

Spas & Retreats
4.9
A small spa with a steady pulse in Windham. Facial steam rises and the scent of botanicals hangs in a quiet, sunlit room.
The Windham Spa

The Windham Spa

$$$

Spas & Retreats

No items found.

Windham

Spas & Retreats
4.9
A women-owned spa with a boutique sensibility and steady hands. Mountain air follows you inside, skin glows on the drive home.
Hotel Vienna

Hotel Vienna

$$

Lodging

No items found.

Windham

Lodging
4.6
Classic alpine lodge rooted in the Windham hills. Croissants, barrel sauna, and staff always ready for a chat or a trail suggestion.
Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant

$$

Lodging

No items found.

Windham

Lodging
Restaurant
4.9
Bright mornings, wood smoke, and antique flourishes in a farmhouse inn just down the road from the slopes. Breakfast carries scents of maple, butter, and fresh herbs.
Jimmy O’Connor’s Windham Mtn. Inn

Jimmy O’Connor’s Windham Mtn. Inn

$$

Bar

No items found.

Windham

Bar
Restaurant
4.4
A classic Irish-American pub tucked behind the slopes in Windham. Burgers and pints land on paper plates, and regulars fill the tables.
Windham Mountain Club

Windham Mountain Club

$$$

Ski Mountain

No items found.

Windham

Ski Mountain
Restaurant
4.3
One of the Catskills’ busier ski draws, mixing broad slopes and a lively base. Lift hum and grill smoke carry all day into the twilight.
Albergo Breakfast Restaurant

Albergo Breakfast Restaurant

$$

Restaurant

🍳 Breakfast

🥞 Brunch

🥐 Café & Bakery

🥗 Vegan & Vegetarian

🥗 Health

Windham

Restaurant
5.0
Mountain mornings start with something familiar, made with intention. Hand-mixed batters, fresh eggs, and sunlight slanting onto old wood.
Mountain King Brewing Company

Mountain King Brewing Company

$$

Brewery

No items found.

Windham

Brewery
Bar
4.7
Small-town brewery pulsing with fresh pours and backyard games. Cold beer in hand, chatter rising off the porch all afternoon.
Eastwind Hotel

Eastwind Hotel

$$$

Lodging

No items found.

Windham

Lodging
Bar
Restaurant
4.7
Modern mountain retreat framed by Windham’s forests and clean Scandinavian lines. Bread rises, guitars ring, and the crew pours at the bar.
Christman's Windham House

Christman's Windham House

$$

Golf Course

No items found.

Windham

Golf Course
Lodging
Bar
Restaurant
4.6
Old Catskills inn rolling out 27 holes on wide ground. Fair plats, honest greens, and pancakes hot off the griddle before the first tee.
The Vineyard At Windham

The Vineyard At Windham

$$$

Winery

No items found.

Windham

Winery
Restaurant
4.4
Tasting room with Catskill mountain views and a local crowd. Flights, cheese boards, and the satisfying buzz of a Saturday afternoon.
Windham Pizzeria

Windham Pizzeria

$$

Restaurant

🍕 Pizza

🥗 Vegan & Vegetarian

🍝 Italian

🍔 American

Windham

Restaurant
4.4
Pizza done the way mountain towns like it—unfussy and fast. Foldable slices, quick greetings, and a space to brush off the day.

Hayfield

Wedding Venue
Maplecrest
Wedding Venue

Hayfield

Maplecrest
A storied 19th-century barn sits among meadow and sky at the edge of Maplecrest. Strings of lights, old trees, and pure Catskills spirit greet every guest.

Eastwind Hotel

Lodging
Windham
Lodging

Eastwind Hotel

Windham
Modern mountain retreat framed by Windham’s forests and clean Scandinavian lines. Bread rises, guitars ring, and the crew pours at the bar.

Skin Concept Esthetics and Wellness SPA

Spas & Retreats
Windham
Spas & Retreats

Skin Concept Esthetics and Wellness SPA

Windham
A small spa with a steady pulse in Windham. Facial steam rises and the scent of botanicals hangs in a quiet, sunlit room.

Antique Rose Inn

Lodging
Windham
Lodging

Antique Rose Inn

Windham
Turn-of-the-century inn where hosts greet guests with hot pancakes and Catskills history. Porch breakfasts linger, mountains crowd in the background.

The Henson

Lodging
Hensonville
Lodging

The Henson

Hensonville
A 200-year-old inn, reimagined with care and fresh perspective. Sun-drenched breakfasts, garden views, and the hum of happy guests.

The Haus Windham

Lodging
Windham
Lodging

The Haus Windham

Windham
Glass cabins, private hot tubs, and Catskill forest all around. Mornings here start clear and slow, with wind through the pines and steam rising.

Hotel Vienna

Lodging
Windham
Lodging

Hotel Vienna

Windham
Classic alpine lodge rooted in the Windham hills. Croissants, barrel sauna, and staff always ready for a chat or a trail suggestion.

The Windham Spa

Spas & Retreats
Windham
Spas & Retreats

The Windham Spa

Windham
A women-owned spa with a boutique sensibility and steady hands. Mountain air follows you inside, skin glows on the drive home.

The Perch Hotel

Lodging
East Windham
Lodging

The Perch Hotel

East Windham
A mid-century mountain hotel set high above the Hudson Valley. Morning fog rolls through the lounge as coffee brews and the ridgeline glows.

Mountain King Brewing Company

Brewery
Windham
Brewery

Mountain King Brewing Company

Windham
Small-town brewery pulsing with fresh pours and backyard games. Cold beer in hand, chatter rising off the porch all afternoon.

Albergo Breakfast Restaurant

Restaurant
Windham
Restaurant

Albergo Breakfast Restaurant

Windham
🍳 Breakfast
Mountain mornings start with something familiar, made with intention. Hand-mixed batters, fresh eggs, and sunlight slanting onto old wood.

Jimmy O’Connor’s Windham Mtn. Inn

Bar
Windham
Bar

Jimmy O’Connor’s Windham Mtn. Inn

Windham
A classic Irish-American pub tucked behind the slopes in Windham. Burgers and pints land on paper plates, and regulars fill the tables.

The Tipp Tavern

Bar
Windham
Bar

The Tipp Tavern

Windham
A straightforward Irish pub with a lived-in Catskills feel. Hand-pulled pints, hearty fare, and a room buzzing with darts and pool.

Taphouse Grille Windham

Bar
Windham
Bar

Taphouse Grille Windham

Windham
Classic bar and grill that feels tied to the heart of Windham. Plates hit the table with burgers, wings, and a draft list that holds its own.

Chicken Run Family Restaurant and Steak House

Restaurant
Windham
Restaurant

Chicken Run Family Restaurant and Steak House

Windham
Families and locals stream in for fried chicken, live music, and plenty of laughter. Platters arrive hot, popcorn is scattered around the tables.

Albergo Allegria Hotel & Breakfast Restaurant

Lodging
Windham
Lodging

Albergo Allegria Hotel & Breakfast Restaurant

Windham
Bright mornings, wood smoke, and antique flourishes in a farmhouse inn just down the road from the slopes. Breakfast carries scents of maple, butter, and fresh herbs.

Millrock Restaurant & Bar Room

Restaurant
Windham
Restaurant

Millrock Restaurant & Bar Room

Windham
Classic Italian plates and good whiskey pour from the bar room, both humming most nights. Wood-fired pizzas, eggplant, and live music linger after dark.

Christman's Windham House

Golf Course
Windham
Golf Course

Christman's Windham House

Windham
Old Catskills inn rolling out 27 holes on wide ground. Fair plats, honest greens, and pancakes hot off the griddle before the first tee.

Prominence Restaurant

Restaurant
Windham
Restaurant

Prominence Restaurant

Windham
🍝 Italian
Dinner feels sewn into the evening here, with plates meant for sharing and lingering.

Windham Mountain Club

Ski Mountain
Windham
Ski Mountain

Windham Mountain Club

Windham
One of the Catskills’ busier ski draws, mixing broad slopes and a lively base. Lift hum and grill smoke carry all day into the twilight.

The Vineyard At Windham

Winery
Windham
Winery

The Vineyard At Windham

Windham
Tasting room with Catskill mountain views and a local crowd. Flights, cheese boards, and the satisfying buzz of a Saturday afternoon.

Brandywine

Restaurant
Windham
Restaurant

Brandywine

Windham
🍝 Italian
Long-running Italian spot where the wood paneling sets the mood. Plates of veal, pasta, and old-school desserts hold down the menu.

Windham Pizzeria

Restaurant
Windham
Restaurant

Windham Pizzeria

Windham
🍕 Pizza
Pizza done the way mountain towns like it—unfussy and fast. Foldable slices, quick greetings, and a space to brush off the day.

Category

Value
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Category

Neighborhood

Neighborhood

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