A stylized illustration of a hand with painted nails making a peace sign inside a red circle, with the text 'THE SUGAR HOLE' in colorful, bold letters around it, on a dark background.

Join us in the Tavern!

New for the 2026 season, we will host a variety of afternoon programming while The Sugar Hole is open. Expect live music, markets, drag, film, and more! See the full lineup below.

Each event will be FREE and open to the public. Performer tips are encouraged! Grab a cone and come inside to see what’s happening. Full bar and snacks also available.

At 5 PM, the Tavern will transition to our evening, ticketed programming.

2026 Season Lineup

August 1 — Mahjong Open Play with Lori Ravis
Reserve a spot for yourself (guided, $25) or a group of four (non-guided, $10 per person) ahead of time by texting or calling Lori Ravis at 773-848-7303. A free drink is included with every reservation! Some tables will be free, drop-in only, so come by and play if the mood strikes you. Sets for guided and drop-in play will be provided. Group reservations should bring their own set. Learn more about Lori.

August 2 — Todd Kessler Residency
Listen to the classics and a few originals. Music sets at 2 PM and 3 PM.

August 8 — TBA!

August 9 — Laura Doherty

August 15 — Puppetpalooza! with Jabberwocky Marionettes

August 16 — Puppetpalooza! with Turn Back Time Records & The Puppet Zoo

August 22 — Tiny Vintage Market + Tiny Dances

August 23 —

Little Miss Ann
Performances at 2 PM and 3 PM

Academy of Irish Music + More!
Starting at 5 PM

August 29 — Sacrosanct Market

August 30 — Sami Scot Piano Karaoke
Puppet duets welcome!

September 5 — HOTDOG HOTDOG Karaoke
Puppet duets welcome!

September 5 — SPECIAL EVENING EVENT: Fragile Rock

September 6 — Tavern closed for a private event, no bathroom access.

September 12 — Lil’ Mike’s: Antique Auction
Hosted by our own Jeremiah Carburetor. Peruse the lots inside the Tavern and then make your bid during auction sessions at 2 PM and 4 PM. Priced to sell!

September 13 — Peter Butter’s Family Jam: A Neurodiverse Storytime and Sing-Along
Neurodivergent families and friends! Join us for sensory friendly performances, crafts, snacks, and storytime as we build community and fundraise for Urban Autism Solutions! 

September 19 — TBA!

September 20 — Wendy & DB

September 26 — The Rainbow Beard Show

September 27 — Todd Kessler Residency
Listen to the classics and a few originals. Music sets at 2 PM and 3 PM. Also performing: Ahna Ell (1 PM) and Zoe Lemon (4 PM).

Colorful puppets and stuffed animals through a circular window of a blue door at The Sugar Hole, a small shop that sells ice cream and drinks, with a sign listing menu items and prices above.

Check back for updates regularly!