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Nightlife Spots in Hudson Valley

Sydney profile pictureSydneyApr 14, 2025

Hello New York State! The Wander team has arrived, and we're excited to share our premium property in upstate New York - Wander Hudson Valley.

New York City isn't the only place that never sleeps; experience vibrant nightlife across the state from one of our luxury vacation rentals in New York.

We want you to have the best time so we’ve put together a list of nightlife experiences for your consideration. Get ready to be a part of some magical nights in the historical Woodstock and Kingston areas!

Live Music at Colony

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Photo by Colony

Nothing says Woodstock like an outdoor concert and fresh drinks! Colony dates back to 1929, where, as the tallest building in town, it served as a stopping point for visitors who were on their way up to the Overlook Mountain House.

During their stop, they dined and listened to big bands in Colony’s great room. Today, the fun continues with "Open Mikes" on Mondays (sign-ups start at 6:00 PM) and the "Best of the Beer Garden Series" on Wednesdays. To stay updated on their events you can visit their page here.

Cucina: Country Chic Italian

Wander Luxury Vacation Rental

Photo by Cucina

  • Distance from Wander Home: 10.9 miles

  • Address: 109 Mill Hill Rd, Woodstock, NY 12498

  • Hours: Sundays to Thursdays, 5:30 PM-9:30 PM. Fridays & Saturdays, 4:00 PM-10:00 PM

  • Contact Number: +1 845-679-9800 

  • Website: http://www.cucinawoodstock.com

For a fine dining experience, Cucina is a modern, country-chic Italian restaurant, located in a restored farmhouse in historic Woodstock, New York. Chef Gianni Scappin has created a social dining experience that offers simple and elegant food.

Their menu includes several gluten-free options based on seasonal and local ingredients. Guests have the choice of dining with some new faces at the 24-seat communal table or in a private dining room.

This hidden gem is only an 18-minute drive from the Wander Hudson Valley home. You can make a reservation by visiting their reservations page.

If fine dining is your kind of thing, check out our guide to upscale restaurants in Hudson Valley.

Cocktails and Nibbles at Stockade Tavern

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Photo by Stockade Tavern

  • Distance from Wander Home: 11.3 miles

  • Address: 313 Fair St Kingston, New York 12401

  • Hours: Thursdays, Fridays & Saturdays 4:00 PM-12:00 AM

  • Contact Number: +1 (845) 514-2649

  • Website: https://www.stockadetavern.com/

If you are in the mood for a world-class, hand-crafted cocktail, look no further than Stockade Tavern. Stockade is a Kingston-based bar known throughout the country for its top-tier mixologists and warm ambiance.

While food selection is limited to nibbles, it doesn't take away the overall quality of the experience. This eclectic spot is only a 19-minute drive from Wander Hudson Valley and a visit here is sure to be one for the memory books. 

Have a Glass at Brunette Wine Bar

Wander Luxury Vacation Rental

Photo by Brunette Wine Bar

  • Distance from Wander Home: 13.4 miles

  • Address: 33 Broadway, Kingston NY 12401

  • Hours: Thursdays &  Fridays, 5:00 PM-10:00 PM. Saturdays 1:00 PM-10:00 PM. Sundays, 1:00 PM-7:00 PM

  • Contact Number: +1 (845) 802-0837

  • Website: https://www.brunettewinebar.com/

Here's something for the wine lovers! Brunette has curated an extensive wine list to satisfy your palate on every occasion! Their selection focuses on organic, biodynamic, and low intervention wines from all over the world.

The aesthetic of the place has been well thought out, from the stylish wallpaper to their diverse menu, which features favorites such as the "Goat Cheese Jam Sandwich," and "Trout Roe Nachos."

They host events on occasion, which can be accessed here. Further, they're only a 24-minute drive from your Wander home.

Stay 'Til late at Early Terrible

Wander Luxury Vacation Rental

Photo by Early Terrible

  • Distance from Wander Home: 11.2 miles

  • Address: 45 Mill Hill Rd, Woodstock, NY 12498

  • Hours: Thursdays & Fridays 17:00 PM-Late. Saturdays and Sundays, 12:00 PM-Late.

  • Contact Number: +1 845-684-7226

  • Website: Earlyterrible.com

Described by guests as, “a magical treehouse utopia,” Early Terrible is an aesthetically pleasing bar, serving handcrafted cocktails and tapas. Service here comes with a smile and the atmosphere is nothing short of unique, featuring tree stump tables, fireplaces, and storybook decorations.

Their menu is said to be constantly evolving sensory experiences and includes popular dishes like their Armenian meatballs and chorizo tacos. Your pets are welcome here, and so are your friends, so round them all up for this awesome experience!

Hungry for more food spots? Check out our Hudson Valley food guide next!


Where to Stay in New York State

From top-rated restaurants to lively bars, there's no shortage of vibrant nightlife in New York, throughout Hudson Valley and beyond.

From Hudson Valley to Athens, Wander offers luxury vacation rentals across New York. Enjoy the bars and restaurants in this guide during your stay at Wander Hudson Valley or Wander Hudson Ridge. Unwind in style with stays at Wander Black Creek, Wander Hillsdale Lakeside, and Wander Sleepy Hollow Lake. Need Wander Concierge can help plan the best vacation you've ever experienced!

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