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bourbon behind the bar wiseguy lounge mass ave

Check Out One of North America’s Top 50 Speakeasies In Indianapolis

Posted on March 9, 2023March 9, 2023 by Rebekah

Yelp recently released its list of the Top 50 Speakeasies In the U.S. and Canada and, lo and behold, an Indianapolis establishment made the list. Wiseguy Lounge is showcased at #25. The nod is well-deserved, with the team at Wiseguy serving up incredible cocktails day in and day out.

Plus, the ambiance can’t be beat. Seating areas anchored by Chesterfield couches take up one side of the space, while a vintage-looking bar with an incredible bourbon selection covers the opposite wall.

woman in red jumpsuit holding kentucky shipwreck cocktail at wiseguy lounge mass ave

I recently visited Wiseguy Lounge — discretely located inside the Goodfella’s Pizza location on Mass Ave — to bring you everything you need to know about this speakeasy-inspired spot’s spring menu.

I spoke extensively to Wiseguy’s head bartender, Richard, who shared that the team switches up the seasonal cocktail menu every three months, giving patrons plenty of options.

spring 2023 menu wiseguy lounge mass ave

My favorite Spring 2023 option is the Kentucky Shipwreck [below], served in a glass tiki mug. You can’t go wrong with this bourbon-based cocktail that also features pineapple rum, Velvet Falernum,  watermelon mint shrub, lime juice, and house-made coconut milk.

kentucky shipwreck cocktail in glass tiki mug at wiseguy lounge mass ave

I also watched Richard whip up a Bears, Beets, Battlestar Galactica cocktail (yes, this is an Office reference, Dwight Schrute fans). This springtime tipple is made with beet infused cachaca, dry curacao, agave, orange, lime, and mint.

beets bears battlestar galactica cocktail at wiseguy lounge

In addition to the rotating libations, Wiseguy has a signature menu featuring drinks like the Broken Hatchet, featuring Four Roses bourbon, orange hazelnut, black walnut, rye bitters, cinnamon, and creme brulee, and the Dirty Smash [below], a concoction comprised of Benchmark bourbon, Demarara Gomme, lemon, and mint.

dirty smash cocktail at wiseguy lounge mass ave

Furthermore, the bartending staff is more than willing to make special requests.

My husband ordered a smoked Old Fashioned and raved that it was one of the best he’s ever had.

smoked old fashioned engulfed in steam wiseguy lounge mass ave

All in all, Wiseguy Lounge is the perfect place to spend any night of the week. They also open at 11 a.m. daily if you want to enjoy March Madness outside of a sports bar.

I (obviously) think any excuse is a good one to visit a speakeasy, so why not Selection Sunday?

interior of wiseguy lounge mass ave

The official description of Wiseguy Lounge reads:

Not in plain sight, but when found, you will experience calm low lighting, dark reclaimed wood, rich leather sofas, elite bourbons, craft cocktails, and knowledgeable well-dressed bartenders that can create any cocktail to satisfy your cravings

brunette woman wearing red jumpsuit sitting on chesterfield couch at wiseguy lounge mass ave

Tell them I sent you.

Wiseguy Lounge currently has 10 locations across Indiana, Kentucky, Ohio, and Tennessee.

Have you been to Wiseguy Lounge?

Wiseguy Mass Ave is located at 545 Massachusetts Avenue Indianapolis, IN 46204

P.S. As always, I love to hear from you on Instagram, @_rebekahbarton

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I’m Rebekah Barton, a lifelong lover of all things fashion and sparkly. I’m a Hoosier by birth but my heart resides in Manhattan, and I make it there as often as I possibly can. I found my place at the intersection of “mom life” and style, for the everyday woman who wants to elevate her look.

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