860 Enterprise Dr, 53086

Our Summer Concert Series kicks off the 2024 season with live music on the patio with local performer Jacob Olson.

🍷🍫 TGIF! Elevate your Friday with our Wine & Chocolate Pairing event on May 17th. Whether you're hanging out with friends, your significant other, or colleagues, this is your chance to treat yourself a little! Enjoy the flavors of four Aspen Sky wines perfectly paired with four gourmet chocolates. It's a match made in heaven! […]

At Aspen Sky, we believe that mothers are the unsung heroes who hold families together with their boundless love and unwavering strength. Even when they're not in sight, their presence is felt in every moment, keeping the family connected and thriving. This Mother's Day, we invite you to join us in celebrating these incredible women […]

☀️🍓Ever hear the saying “Don’t mess with a good thing?” … well, we did anyway! Let’s toast to warmer weather and cooler sips with an irresistible flight of 4 (5oz) summer approved Ol’ Fashioneds! 🍓☀️

🕯️🍷 Join Kristi from Beneath the Pines for a Candle Making Workshop at Aspen Sky! 🕯️🍷 Get ready for a fun-filled evening of creativity and relaxation as we dive into the art of candle making. Sip on a glass of Aspen Sky wine while you craft two beautiful candles to take home. During the workshop, […]

Our favorite words… Wine Holiday! ✨ In honor of National Moscato Day, we are highlighting our very own sweet white option, the Wisconsin Sweet White. This gem is 100% Wisconsin. Boasting notes of honey and rich stone fruits, it is a sweet treat on its own, but also pairs wonderfully with a variety of snacks! […]

Have plans for Cinco de Mayo yet? Why not join us at Aspen Sky for our Cinco de Mayo Fiesta! Come enjoy festive music, games, great food options provided by Ney’s Premium Meats and Sweets, and of course, our insanely popular margaritas! Free to the public!!!

Big hats and the most exciting two minutes in sports. Join us for horse race drawings, a child friendly scavenger hunt, special themed cocktails, giveaways and more! Free to the public with the option to be in the “winning circle” for $25. The winning circle ticket includes- Two drawing tickets for free for a chance […]

Get ready for a night of fun at our monthly Aspen Sky Gives Back Trivia Night! It's all about having a blast with friends, sipping on some drinks and supporting a good cause. This month proceeds will go to The Friends of the Slinger Library. $20/team entry fee - Teams of 2-8 people are welcome. […]

Need just the right snack to make your nights in next level?! We got you! Join us for a delicious duo of four Aspen Sky Wines each matched to the perfect popcorn flavor! It’s a night of fun with a pop of flavor in every sip.

We are moving our flight nights to the morning with a special weekend edition of Bloody Mary Brunch Flights. We will be serving up four different Bloody Mary tasters along with a traditional skewer and pretzels. *20% off for Social Club members. This is a ticketed event. Space is limited. Purchase your tickets today!*

Doughnuts & Wine?! It’s a yes from us! Taste the greatness of these flavors as we pair four Aspen Sky Wines with four delectable doughnuts! Donut miss out on this one 🍩