No. 5 – 1933 Lounge
The stairway to the 1933 (named for the year Prohibition ended) leads back in time. At the top, waitresses in scandalously small red dresses cater to the suits in a lounge that’s as elegant as it is quiet.
No. 6 – Nicky Blaine's
With no windows in sight, hours can disappear at this Monument Circle man cave, one of the last bastions for cigar-smokers in the city.
No. 7 – Bluebeard
The cocktail menu changes seasonally, so don’t go looking for “the usual.” And the bar offers high-concept snacks ranging from charcuterie to pickles.
No. 8 – The Brass Ring Lounge
Years before the speakeasy trend made its way to Indy full force, this establishment featured Jazz Age photos on the wall and classic cocktails like the Sazerac.
No. 9 – The Chatterbox Jazz Club
This tiny joint is a total dive. But the jazz musicians who perform there, and the toe-tapping art-schoolers and wine-sipping literati who crowd the shotgun bar to hear them, really class things up.
No. 10 – Wellington Pub
There are plenty of other holes-in-the-wall in Indy, and you can’t throw a dart (another Wellington pastime) without hitting a corporate bar marketing itself as a British-themed pub. But the leaded glass and woodwork here make most of those other places seem like a trip to the loo.
No. 11 – Radio Radio
It has built a reputation for being the place to knock back a few drinks while taking in the best indie rock you haven’t heard yet.
No. 12 – Slippery Noodle Inn
You can't fault owner Hal Yeagy for taking what was essentially a sad little shotgun saloon and turning it into a blues mecca, sprawling grownup amusement park, and Indiana’s most famous nightspot.
No. 13 – The Aristocrat Pub & Restaurant
A bar crowd that had thinned (and aged) noticeably since the Aristocrat opened 80 years ago now seems to be reinvigorated, even on weeknights.
No. 14 – MacNiven's
European and American football share time on the TVs here, but in the summer, most patrons crowd around the garage-door windows and focus their attention on the stylish denizens of Mass Ave.