Downtown Olly’s
NEIGHBORHOOD: Upper Canal
In between the Stutz and the Scottish Rite Cathedral, this vibrant neighborhood sanctuary stays open from 7 a.m. to 3 a.m. daily, keeping the kitchen staffed 24/7 for indoor/outdoor dining and food delivery service. Vestiges of the original sports bar now share space with sparkling lights and rainbow Pride flags—Olly’s evolved soon after opening to accommodate a more diverse audience, earning a “Best LGBTQ Bar in the Country” nod from the Bar & Restaurant Expo in 2022. Biscuits and gravy, fried green tomatoes, and double-breaded chicken fingers stand out among the food lineup, and the live entertainment schedule includes piano bar singalongs, trivia nights, burlesque shows, and “Ollywood” karaoke.
822 N. Illinois St., 317-636-5597
OPEN SINCE: 1995
THE USUAL: Mimosas and bloody marys during the weekly Glam Slam Drag Brunch
English Ivy’s
NEIGHBORHOOD: Saint Joseph
A central gathering place in the historic Saint Joseph district, English Ivy’s is the kind of inviting neighborhood haunt where you can wander in and spot a friend already posted up at the bar with a bloody mary and a pile of pull tabs or slide into one of the brown pleather booths for a quiet catch-up over margaritas and Boom Boom Shrimp. The menu is surprisingly long and involved, blending pub grub with proper steaks and comfort classics such as Wednesday night’s fried chicken dinner and Friday’s prime rib. Long known as an iconic gay bar in the heart of Indianapolis, the Ivy has been a safe, central hub for the city’s LGBTQ+ community for decades—equal parts welcoming, unpretentious, and a fabulously good time.
944 N. Alabama St., 317-822-5070
OPEN SINCE: 1999
THE USUAL: The Ivy’s Ass (1800 tequila, beer, ginger beer, simple syrup, and lime)
The Living Room Lounge
NEIGHBORHOOD: Chatham Arch
Connecting to a familiar 1920s-era building that’s functioned as a roller-skating rink, a car dealership, and now The Cabaret, this inclusive neighborhood dive serves a loyal community of regulars and the occasional visiting celebrity. With a name like The Living Room, patrons know this is going to be a comfortable spot to just kick back and chill. Although with pool tables, darts, live music, and DJs spinning tunes beneath the disco ball, guests can also be as lively as they want. You’ll hear everything from Elvis and Prince to Glorilla on karaoke nights, and the kitchen stays open late cooking up wings, fried cauliflower bites, and hand-breaded tenderloins.
934 N. Pennsylvania St., 317-635-0361
OPEN SINCE: Early 1980s
THE USUAL: Monkey Punch, a boozy fruit punch concoction
The Whistle Stop Inn
NEIGHBORHOOD: Wholesale District
On March 14, 2024, Governor Eric Holcomb signed HB 1086 on this very bar top to bring happy hour back to Indiana. Spitting distance from Lucas Oil Stadium, the Indiana Convention Center, and the Indiana Statehouse, The Whistle Stop’s a popular hang for politicians, out-of-towners, football players, and Colts fans. The beer-friendly menu details brisket-topped fries; wings by the pound with eight different sauces; deep-fried pizza rolls; and exotic meats such as elk, venison, and camel burgers. House cocktails cover all the whiskey, rum, vodka, and tequila bases, while boozy house-made ice cream makes a sweet finale.
375 S. Illinois St., 317-602-6334
OPEN SINCE: At least the mid-1970s
THE USUAL: OMH Margarita (with the traditional ingredients plus mango habanero whiskey and Sprite)
