There’s something fun about a good game—especially when it’s easy to jump into, doesn’t take all night, and comes with a glass of wine in hand. That’s exactly the idea behind Pour & Play – Lawn Game Nights, our new Thursday evening event built around casual, pick-up style play.

As the days grow longer and the weather warms up, we’re excited to welcome you back to Aspen Sky for another unforgettable season of live music with our Patio Concert Series! Join us every Friday evening on our scenic patio for great music, delicious food, and refreshing drinks – all set against the backdrop of our beautiful tree-lined lot.

Winter may bring chilly days and frosty nights, but at Aspen Sky, we’re turning up the heat with our Live at Aspen Sky concert series! From January through April, join us for unforgettable evenings filled with live music, great wine, delicious cocktails, cold beer and the best vibes to carry you through the chilly months.

The holiday season is upon us, and there’s no better way to soak up the spirit of Christmas than with a visit to Aspen Sky’s first-ever holiday pop-up bar: The Jingle Bell Bar! Located in our cozy, rustic Barrel Room, this one-of-a-kind holiday experience will leave you feeling merry, bright, and ready to toast to the most wonderful time of the year.

Summer is a popular season for weddings in Wisconsin (all two weeks of it!) and it’s easy to see why. The warm weather, long days, and vibrant landscapes create an idyllic setting for couples looking to celebrate their love. Whether you envision an outdoor ceremony, a patio cocktail hour, or gathering fireside late in the evening, summer offers endless possibilities especially at Aspen Sky. In this article, we’ll explore the many reasons why summer weddings in Wisconsin are so special and why you should consider this sun-soaked season for your big day.