Chicago's 'Hobbit Door' Ice Cream Shop Is A Little-Known Gem With A Unique Family-Friendly Surprise

If you're like us, you've probably often wondered: "Hey, why isn't this person who's handing me my ice cream a puppet?" Thankfully, the good folks at the Sugar Hole in Chicago have answered the call and are ready to supply you with two scoops of performative puppetry with a side of rainbow sprinkles. Located right along North Elston Avenue in Irving Park (an underrated neighborhood with vintage mansions and trendy breweries), the novelty ice cream shop has precisely what every family needs: Ice cream, puppets serving said ice cream, and a blue "hobbit door" with a curtain and little porthole out of which said puppets and ice cream emerge. It's a magical thing.

The Sugar Hole is a relatively new, 2024 addition to the Color Club, a neighborhood art center and gallery open since 2021. The Sugar Hole arose from a dinnertime conversation between co-owners Josh Dihle and Abby Monroe, as their two-year-old son's puppets prompted the idea. Dihle asked of their fledgling shop, "What if it was a little puppet hand that came out and took your change or took your money when you paid?" to which Monroe replied, "Maybe just: puppets should work there" (via WBEZ). Thus, a legend was born. The couple had been wanting to open an on-the-premises food window at Color Club, and naturally, kids love it.

Understandably but unfortunately, the Sugar Hole is a pop-up seasonal affair. Open from about mid-May through Labor Day, the Sugar Hole serves up soft serve cones, ice cream cups, cold brew, and even alcohol during the hottest months of the year. If you want to partake, you've got to strike on the weekends from 3 p.m. to 8 p.m. Continure your family-friendly adventures at Oz Park, boasting whimsical sculptures and gardens just 7 miles away.

Judging by the Sugar Hole's menu on the hobbit hole door, the core items are pretty simple. You can get a cup or cone of chocolate, vanilla, or swirl ice cream for a reasonable $5, plus chocolate or rainbow sprinkles. And judging by the Color Club's Instagram, each year features changes and/or expansions to the menu. For 2025, there's a new soft serve flavor, sssstrawberrry, plus cold brew from Chicago's own Backlot Coffee. There are also hand pies from Chicago's Bang Bang Pie and Biscuits and dairy-free options.

Because puppets are the hosts at Sugar Hole, there's an array of fabric and fur on hand to help you with your order. The puppet lineup consists of Aurora Bearialis, Puddles, Moolisa the cow, and Jeremiah Carburetor, a mustachioed ne'er-do-well in a cowboy hat. You might also catch a glimpse of a yellow Kermit the Frog lookalike for folks who go in for amphibians. 

Being attached to an art center, Sugar Hole comes with loads of things to do. The building itself has a history going back to 1922 as the first meeting for Chicago's Independent Order of Vikings, which was apparently a thing. Now it's a community hub "to enjoy music, art, expression, and experimentation," per its website. The Color Club's calendar is chock-full of events, from concerts and improv quilting to kids' yoga and making mirrors from broken tiles and shells. So hop to it and visit the most weird and cool pit stop you'll find in Chicago. For another unique dessert experience, check out Indiana's ice cream parlor with the world's largest collection of cookie jars.