Nightlife: Wander Hudson Valley

Heard that Upstate New York is boring? Not true at all!

Sydney Danson
SydneyTravel Concierge & Writer
Nightlife: Wander Hudson Valley

Hello New York state! The Wander team has arrived and we are excited to share our luxury vacation home in Hudson Valley with you.

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

Wander Luxury Vacation Rental

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 or through Wander Concierge.

Cocktails and Nibbles at Stockade Tavern

Wander Luxury Vacation Rental

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. 

Ice-skating and Drinks at the Ole Savannah

Wander Luxury Vacation Rental

Photo by Ole Savannah

Located on the Kingston Waterfront, in the historic Rondout, Ole Savannah is a bar, restaurant, ice skating rink, and events center altogether. The perfect place for a family-friendly outing or a casual date night or whatever the occasion.

Guests are bound to feel right at home because the staff here is all about Southern hospitality. The restaurant specializes in Southern comfort food, featuring bone barbecue, fried chicken, pecan pies as well as great bourbon and craft beers to drink.

The ice rink is open from Mondays to Saturdays, 9:00 AM-10:00 PM, and Sundays, 10:00 AM-8:00 PM. Tickets can be purchased upon entry or through their booking site. The cost of a ticket is $20 with rentals and $15 without.

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.

Hudson Valley West Coast Swing

Wander Luxury Vacation Rental

If you need a mood-booster, attending Hudson Valley West Coast Swing's Tuesday night dance sessions might do wonders for your mental health. Classes are led by the instructor and founder Pam Marshall and Jun Ogata, who specializes in East Coast Swing, Argentine Tango, as well as West Coast Swing.

For beginners, classes start at 7:00 PM, followed by a guided practice at 7:45 PM and then finally, the dance session at 8:30 PM sharp. The classes and dance will cost you only $20 and are located only 20 minutes from Wander Hudson Valley. To view their full dance schedule you can click here.

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!

Know Your Food with Lunch Nightly

Wander Luxury Vacation Rental

Photo by Lunch Nightly

  • Distance from Wander Home: 11.9 miles

  • Address: 636 Broadway, Kingston NY 12401

  • Hours: Thursdays, Fridays & Saturdays-Dinner is 5:00 PM-10:00 PM. Bar until 11:00 PM

  • Contact Number: +1 845-663-2028

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

For the responsible consumer who would like to know exactly where their food is sourced, Lunch Nightly is your new favorite spot. This restaurant is dedicated to supporting its community by offering high-quality produce and meats at an accessible price.

Further, they only utilize independent farmers and producers who care about animal welfare, which they have listed here.

With attentive staff, exquisite decor, a deliciously sustainable menu, as well as the option of outdoor seating, you really can’t go wrong here…oh did we mention they are just a 19-minute drive from your Wander Hudson Valley vacation rental?

Lis Bar

Wander Luxury Vacation Rental

Photo by Lis Bar

  • Distance from Wander Home: 12.8 miles

  • Address: 240 Foxhall Avenue Kingston, NY 12401

  • Hours: Thursdays to Mondays 5:00 PM–close. The kitchen closes at 9:00 PM.

  • Contact Number: +1 845-514-2350

  • Website: https://www.lisbar.com/

There's nothing quite like the taste of food, prepared on a wood-fired grill. Served with natural wine, the New York Times can attest to the fact that Lis Bar does this best.

Located in Kingston this spot is all about simplicity, cozy vibes, and creative cocktails. Their diverse menu consists mainly of Polish dishes, like their "pierogies" which are a local favorite. Their upcoming events can be viewed here.


There is so much history and culture in these parts and a number of unique spots that await your discovery. A friendly reminder that the Wander concierge chat is here to assist you with anything you need during your nights out in Hudson Valley!

If you didn’t find what you were looking for on this list just remember that you are in New York state and the heart of the party is only a two-hour drive from your Wander Hudson Valley Vacation home. So go out and enjoy, New York is your oyster!  We wish you a wonderful and safe night out! 

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