5 Speakeasy Lounges for Your Next Group Outing

By Kristine Hansen | Photo © The Dark Room

The cozy, intimate settings of bars and lounges — especially those channeling a 1920s speakeasy vibe, but without the need for a special code or password to enter — just might be the perfect place for your group to meet. With private rooms or spaces, these can be used as a social, after-hours networking event after a day of meetings or as an incentivized outing. If you want to create a memorable outing for your group, here are some tips on how to utilize a speakeasy bar and what the options are for food and beverage. These places can also develop mocktails to further broaden accessibility for groups.

Bryant’s Cocktail Lounge, Milwaukee

This South Side institution dates back to 1938 when then-owner Bryant Sharp turned his two-year-old beer hall into a cocktail lounge. It’s also where the Pink Squirrel (white crème de cacao, heavy cream and crème de noyaux) was invented. The Velvet Lounge is an upstairs private room available weekdays that can seat 40 people and is aptly named for its black-velvet wallpaper. As food is not served on site, groups can either bring in their own food or have it catered.

“People seek out Bryant’s because it’s a unique experience. A lot of times, it’s bringing in groups from out of town,” says owner John Dye. “It’s a way to show off part of Milwaukee, Wisconsin … a unique part of it.”

Bryant’s works closely with event planners to develop a menu of eight cocktails just for the group. “There’s always an Old Fashioned, which is popular in Wisconsin and sometimes we’ll put an ice cream drink on. We try to vary it through our list, to go from sweeter dessert-y to more adventurous. The best thing in my view is to have something for everybody,” says Dye.

The Outsider, Milwaukee

Within this rooftop bar at Journeyman Kimpton Hotel, smaller spaces are carved out so that groups can easily reconnect over drinks, which include wines by the glass and seasonal cocktails like Toasted Marshmallow Old Fashioned. “Once we get down into the 40s and the 30s on a consistent basis, that’s when we close the garage doors,” says Joshua Waeghe, Director of Food & Beverage for The Outsider. “The place is still very cozy during the winter. We have two big fire pits inside as well.”

Partnering with the hotel’s restaurant Tre Rivali and its chef Paul Funk can mean shareable, Italian-inspired bites to accompany a private event. Seated dinners are hosted in the Founders Room (with an enclosed south-facing patio) and buffets during afternoon hours can be held in The Outsider’s main area. With its retractable windows, and seating for up to 30 people, the Crow’s Nest is always a big draw, says Waeghe. “If it’s in season, it can be airy and breezy in there. During the winter months, we’ll have the fire pits.”

Groups have also bought out the entire space. In one case, for 250 people, “the only space on the ninth floor that wasn’t accessible was the outdoor covered area we open up in the summer,” says Waeghe. “It was spacious because of the activation we had. Everyone was pretty spread out.”

The Dark Room, Milwaukee

Tucked onto the second floor at Saint Kate – The Arts Hotel in downtown Milwaukee, this dining space functions as a private venue for groups of 30 people or less. Like the rest of the hotel, it’s very easy on the eyes and high on design, with a swanky vibe illustrated through tall, lit candles on the tabletops; art hung on the walls; and warm color tones like burgundy (for the walls) and navy (plush seating).

As its name implies, The Dark Room is dimly lit, but this is fine (and carries elegance) as long as you aren’t asking participants to view a presentation or consult printed materials. The vibe is quiet, romantic and serene, with food choices on the private-dining menu that skew surf and turf and can be customized for a group. For example, on the Graze & Carve menu there’s the ability to select hors d’oeuvres, grazing boards, entrees (prime rib, salmon, chicken and a porchetta roll), sides and dessert; and the three- and four-course plated menus also offer choices.

Another venue in the hotel, Giggly, is all about sparkling wine and that mantra continues at The Dark Room where meals can be paired with glasses of French Champagne or bubbles from outside of France.

Velvet Buffalo and The Rooftop, Beloit

Located within the 34-room Hotel Goodwin, a boutique property in downtown Beloit, Velvet Buffalo is a modern Italian restaurant sporting a speakeasy vibe with moody lighting, artwork and brass fixtures. This would be ideal for small groups dining together although a private space is not available to reserve. At The Rooftop — a glass-enclosed, 1,000-square-foot rooftop space — up to 60 people can be accommodated for an event. This could even mean a buy-out, where the group has sole, exclusive access. Examples of how to use the space are a private mid-day luncheon, after-work drinks (on the menu are classic cocktails with a seasonal twist, like Cran-Merry Mule and Peppermint Mocha Espresso Martini) or a casual dinner (meatball sliders, mussels and a cheese-and-sausages snack board are among the options). At night, the rooftop space feels even more intimate.

Driftless Glen Distillery, Baraboo

This spirits maker’s Baraboo River Room — so named for the Baraboo River out back — is sunny and bright, thanks to walls of windows, and can seat up to 50 people. There’s no fee to rent the room so long as a food-and-beverage minimum is reached. Because the distillery is also home to a restaurant, as well as a full bar, catering (either buffet or plated) can be ordered for breakfast, lunch and dinner, providing lots of flexibility for groups who want to host a working meeting over a meal or offer a fun outing. Meal items from day to night include waffles, jambalaya and elk sliders, as well as Italian dishes, and starters such as crab cakes and a cheese and cracker platter. Naturally, cocktails folding in their spirits can also be ordered. To learn more about the distillery’s story and production process, tours can be arranged for larger groups, in addition to the tours that start every hour on the hour between 11 a.m. and 6 p.m. or 7 p.m. Thursday through Sunday.