Photo courtesy Hotel Indy
Wabash Old Fash
Cannon Ball Lounge
Rye mingles with rustic sorghum, local bitters, and Hotel Tango orangecello for a stout but sophisticated take on the classic brown drink served at Hotel Indy’s rooftop lounge. 141 E. Washington St., cannonballindy.com
Cognac Old Fashioned
Ball and Biscuit
Wisconsinites and other upper Midwest drinkers prefer brandy in their supper club Old Fashioneds, and the option with Pierre Ferrand 1840 cognac at Mass Ave’s king of cocktail bars comes closest to this slightly sweeter spin. 331 Massachusetts Ave., 317-636-0539, ballandbiscuit.com
Walk the Line
West Fork Whiskey
You can opt for a dessert-worthy peanut butter version or a barrel-aged revision with spicy chocolate bitters, but, true to its name, this fruitier, rye version with a pomegranate-black cherry syrup walks the line toward a Manhattan, even getting served up in a coupe glass without ice. 1660 Bellefontaine St., 317-672-7468, westforkwhiskey.com
Gilded Gent
Union 50
The creative mixologists at this longtime Cunningham pleaser aren’t bound by tradition, which shows in this south-of-the-border version mixing mezcal and scotch with a spicy demerara syrup that has an earthy, smoky edge, made all the more evident when garnished with a chocolate cigarette tipped in gold dust. 620 N. East St., 317-610-0234, union-50.com
Classic Old Fashioned
Wiseguy Lounge
Few cocktails feel more like the original than when the barkeeps at this swank whiskey-centric saloon tucked behind Goodfellas torch a lemon peel, stir Ancient Age Kentucky bourbon and simple syrup together and serve up the perfect pour. 545 Massachusetts Ave., 317-602-3401, goodfellaspizzeria.com/wiseguy-lounge
Smoked Old Fashioned
Shelby Street Speakeasy
Not only can you call your own bourbon, but you can select one of four smoke choices (hickory, mesquite, and cherry) to lend a custom, woodsy character to a cocktail you’ll sip in some of the most charming retro environs south of the city. 2849 Shelby St., 317-875-1932
Plat 99 Old Fashioned
Plat 99
The house old fashioneds at the Alexander’s second-floor art bar are textbook on their own, but a season upgrade gets you West Fork Whiskey’s Old Hamer bourbon sweetened with hickory syrup and smoked in a swing-top bottle you pour yourself. 333 S. Delaware St., 317-624-8200, thealexander.com
