"I also worked on Smokefree 2000 in the 1990s and getting the statewide smoking ban," Waunakee Village President Kristin Runge told the board on April 6, before casting a vote that would let a cigar lounge sell tobacco products a few blocks from her own office.
That is the strange center of the story behind The Tasting Room's new Main Street location: a village president who helped build Wisconsin's smoking restrictions is the same official who had to sign off on a workaround to them, for a business she and most of her board otherwise wanted downtown. It took four years, at least three different proposed addresses, a licensing fight the village attorney called a legal trap, and a split vote on a Plan Commission that doesn't usually split, to get there.
A Downtown Debut, Four Years in the Making
The Tasting Room isn't new to the Madison area. Jason and Jessica Smith have owned the cigar lounge and cocktail bar in Monona since 2017, in a building the business has occupied under various configurations since 1995. It's a known quantity: a 3,500-square-foot space with a walk-in humidor, a ventilation system that cycles fresh air every four minutes, and a following built over three decades in one town.
Waunakee has been on the Smiths' radar since 2022, when they first pitched the village on a roughly 7,000-square-foot building near Kilkenny Farms Park, next to Kwik Trip on Water Wheel Drive, with a large outdoor patio, fire pits, and an indoor golf simulator. That site didn't pan out. By the time village officials were recapping development plans for 2026, the business's target had shifted again, this time to a spot described only as near Buck & Honey's on the other side of the village. What actually opened, a few months after that, was neither of those: 114 E. Main Street, inside the Village Crossing retail center, the same building that's home to Lone Girl Brewing Company, in a storefront that keeps the historic Koltes Lumber facade intact.
That shift, from a greenfield outparcel to a preserved building on the actual Main Street, is the detail worth sitting with. It's a smaller footprint, planned at approximately 6,000 square feet rather than 7,000, but it's downtown, in a building the village has already spent effort keeping historically intact. Trading suburban square footage for a Main Street address with a legacy facade is not a neutral choice. It's a bet that foot traffic and street presence beat parking and patio size, and it's the kind of bet that comes with a different level of scrutiny.
What Actually Got Argued About
The scrutiny showed up first at the Plan Commission level. On March 9, 2026, commissioners approved two Conditional Use Permits for the Main Street site. The first covered the core business: full-service bar and lounge, a banquet area, retail cigar and pipe tobacco sales, and the outdoor patio. The second, and more contested, permit covered outdoor eating, drinking, and smoking specifically, with conditions attached for fencing, time limits on outdoor service and music, and a Waunakee Fire Department review of any fire pits.
That second permit passed 6-1. The dissenting vote came from Commissioner Melissa Hunt, who objected not to the concept but to a provision added mid-meeting by Commissioner and Village Trustee Joe Zitzelsberger, which gave the village the right to review the permit again if the volume of smoke generated outdoors became a problem. It's a narrow disagreement on paper. In practice, it's the first sign that this project would need to clear the village's comfort level on smoke, not just noise or parking, in a way most Main Street businesses never have to.
The Legal Snag Nobody Saw Coming
The bigger fight happened a month later, over whether the business could sell tobacco at all. Wisconsin's statewide smoking ban makes indoor cigar lounges rare, and The Tasting Room's plan depended on a grandfathered tobacco license, one originally issued to an establishment in Wisconsin Dells and purchased by the Smiths to bring to Waunakee.
The Village Board first took up the license application on April 6 and immediately hit a snag: several board members had already voiced opposition to public smoking at prior meetings, and Village Attorney Bryan Kleinmaier needed time to sort out whether the license was even transferable. He came back on April 20 prepared to tell the board they had little choice but to approve it. Then a memo arrived. On Friday, April 17, the Wisconsin Legislative Council sent Kleinmaier a staff opinion suggesting the Dells-issued license might not actually permit the business to relocate to a new municipality at all, a conclusion that directly conflicted with a separate 2021 memo from the same office. Kleinmaier told the board they were "caught in the middle on a state issue" with no clean answer either way.
What tipped the vote wasn't the legal memo. It was procedure. Village Administrator Todd Schmidt reminded the board that Wisconsin's Department of Revenue requires every tobacco and liquor license to be evaluated on the same criteria, regardless of the applicant, and that The Tasting Room was, on paper, just another applicant standing next to every other license the board had approved without dispute. A letter of support from Hovde Properties, which owns the Village Center building, didn't hurt either. No neighboring business objected. The board approved the license on April 20, the last municipal approval the business needed to open.
What You'll Find Inside
Once the doors open, the space is built to feel like a destination rather than a quick stop. Based on the plans submitted to the village, residents can expect:
- A full-service bar and cocktail lounge with a banquet area for private events
- A retail cigar and pipe tobacco shop with an expanded humidor and private storage lockers, a step up from the Monona location's setup
- An outdoor patio with fire pits, subject to the fencing and fire department conditions attached to its permit
- An indoor golf simulator, part of the original concept the Smiths carried over from their first Waunakee pitch
- Tapas-style food options, an idea Jessica Smith floated when the Kilkenny Farms concept was still on the table
As of late August, The Tasting Room's own job postings were still advertising openings for "both our award-winning Monona location and our new Waunakee location opening Summer 2026," which puts the doors somewhere between imminent and already unlocked by the time you're reading this. If you haven't walked past 114 E. Main Street in a couple of weeks, it's worth the detour.
Why This Took So Long Says Something About Main Street
None of this happened because Waunakee doesn't want new business downtown. Village officials court development actively, and nobody on the board or commission voted against the concept itself. It happened because a legacy facade on Main Street carries a different kind of weight than an outparcel near a Kwik Trip. When the Smiths were pitching a site near Kilkenny Farms in 2022, the conversation was about parking and square footage. When they moved the same idea into a historic downtown storefront, the conversation became about smoke volume, indoor air law, and a village president's own decades-old advocacy against exactly the thing she was now being asked to license.
That's not a coincidence. It's what happens when a business tries to occupy the literal center of a small village rather than its edge. The same corridor near Kilkenny Farms that the Smiths originally considered is now anchored by a new Aldi, a straightforward retail use that cleared approvals without controversy. Main Street asked more of The Tasting Room precisely because Main Street means more to the people who sit on its boards. If you're watching how downtown Waunakee evolves, that's the pattern to track: the harder the fight over an address, the more that address has come to matter.
For a closer look at how downtown activity and pricing intersect in Waunakee's current market, see our recent breakdown of what the village's 2026 median actually buys.
Whether you're a longtime Main Street regular or you're just now hearing about the fight over 114 E. Main, Waunakee keeps giving residents reasons to pay closer attention to what's happening a few blocks from home. If you're curious how the village's ongoing changes might affect your own plans, from a growing downtown to new development on its edges, Beth Baty is always glad to talk through what it means for you. Let's Connect.
