By Lori Fredrich Senior Food Writer, Dining Editor, Podcast Host Published Dec 08, 2023 at 11:04 AM

Snuggle up with some holiday cheer as OnMilwaukee shares stories of everything merry and bright in the spirit of the season.

The OnMilwaukee Ho Ho Holiday Guide is brought to you by Educators Credit Union, Harley-Davidson Museum and MolsonCoors

Natty Oaks Pub & Eatery, 11505 W. National Ave., is home to a variety of attractions, from its spacious summer Pawtio to seasonal Santa Chalets and Domes.

But did you know that it’s also home to a speak-easy style bourbon lounge that boasts a free jukebox and a collection of photographs that date back to the 1940s?

If you didn’t, you’re not alone. You may be among hundreds of customers who have passed through the doors of Natty Oaks over the past couple of years without ever suspecting that there was a second bar – called The Oaks Lounge – located just beneath the floor of the main dining area.

Interior of The Oaks LoungeX

Natty Oaks owner John Roots reimagined the space 2021, the goal was to create a laid-back bourbon bar and lounge for folks looking for a low-key environment and an excellent selection of bourbon, whiskey and scotch.

The Oaks Lounge

And that’s exactly what folks will find when they visit The Oaks Lounge, an underground hideaway that serves as a hidden respite from the busy world above.

The entrances to the Lounge aren’t particularly hidden. There’s one on the backside of the bar, which boasts signage for the lounge as well as a red light, which is lit up when the lounge is open (on Friday and Saturday evenings). There’s also access through the stairwell in the Natty Oaks dining room.

Access door for The Oaks LoungeX

Both allow entry through a secret bookcase door that underscores the “hidden” aspect of this gem. (Soon, guests will be able to dial the number for Natty Oaks sister restaurant, Henry Flach, on the nearby telephone which will signal the door to pop open for entry).

Once inside the space, guests will find a space reminiscent of a mash-up between a Northwoods lodge and an upscale “mancave” showcasing brick-look walls, wooden paneling, and a congenial bar that seats about 10 guests.

The bar at The Oaks LoungeX

Leather couches and chairs provide enough space for about 20 guests to sit comfortably and socialize with friends or enjoy a round of cards, cribbage or Shutbox (AKA Shut the Box), a fast-paced, easy-to-learn dice-based game that originated in English pubs. 

On the walls, guests will find family photos that date back to the 1940s that were donated by a great grandson of the original owners. Among them is a portrait of Gordon and Myrtle.

Gordon and MyrtleX

There's also a handsome portrait of Duke the dog and his handsome boy.

“They were part of the Milwaukee Kennel Club, so they raised dogs on the land,” notes Roots. “That’s part of why we call our patio the Pawtio. It’s an homage to those days.” 

Duke and his boyX

Currently, the lounge is also decorated for the holidays, so guests will find tastefully placed lights, wreaths, Christmas village displays and various holiday tchotchkes along with fun elements like the leg lamp from the film “A Christmas Story.”

Christmas village displayX

At the bar, guests will find a substantial whiskey collection, including some rarities like a collection of Blanton’s bourbon. Since whiskey is offered by the ounce, guests can also create their own flights and sample their way through old or new favorites.

Guests can also order a beer or choose from a collection of classic cocktails, including The Dirty Stallis martini, Manhattan, Old Fashioned, Paloma, a Tequila Daisy and creations like the Rhuby Slipper (rhubarb gin, lemon, elderflower syrup, lemon lime soda) and The Yup Daiquiri (rum, lime and simple syrup).

Drinks at The Oaks LoungeX

“People love being able to have a place to go for craft cocktails, a glass of bourbon or even just a beer,” says The Oaks bartender Garrett Pomeroy. “We have regulars who come to visit us at least once a month. Sometimes they bring friends, and in nearly every case they’re really surprised. Most of them never knew we had anything like this here.” 

“Many people are also surprised by the selection of whiskey and bourbon that we have,” he notes. “Bourbon snobs come down and their eyes get big because there’s a huge variety… We really do have something for everyone.”

Upcoming events

The Oaks Lounge offers monthly tastings of different spirits and cocktails. But guests can also watch for special events. Among the upcoming offerings is a Great Gatsby-style pre-New Year’s Eve party which will take place on Saturday, Dec. 30 from 7:30 p.m. to 12:30 a.m. Guests are encouraged to dress up in their best 1920s vintage attire and stop by to enjoy appetizers, a costume contest and cocktails made with spirits from Dancing Goat Distillery.  Tickets are $40 per person and can be purchased online.

The lounge is also available for private parties of up to 35 guests. Interested parties can reach out to Natty Oaks by email at

The Oaks Lounge is open September through May with hours on Friday from 4 to 11 p.m. and Saturday from 7 p.m. to midnight.

Lori Fredrich Senior Food Writer, Dining Editor, Podcast Host

Lori is an avid cook whose accrual of condiments and spices is rivaled only by her cookbook collection. Her passion for the culinary industry was birthed while balancing A&W root beer mugs as a teenage carhop, fed by insatiable curiosity and fueled by the people whose stories entwine with each and every dish. She’s had the privilege of chronicling these tales via numerous media, including OnMilwaukee and in her book “Milwaukee Food.” Her work has garnered journalism awards from entities including the Milwaukee Press Club. 

When she’s not eating, photographing food, writing or recording the FoodCrush podcast, you’ll find Lori seeking out adventures with her husband Paul, traveling, cooking, reading, learning, snuggling with her cats and looking for ways to make a difference.