For some of the most inventive cocktails in Louisville, head to the upstairs bar at Butchertown Grocery. Located in an old market inside one of the city’s most recently revitalized neighborhoods, this restaurant was founded by chef Bobby Benjamin, My Morning Jacket drummer Patrick Hallahan, and high-stakes lawyer Jon Salomon. The drinks are as unique as the ownership team, with sophisticated, yet off-kilter, picks like the Heart Attack and Vine, made from Beefeater gin, bacon-washed Campari, and mulled wine.

LouVino is a bar that serves up small plates and big wines. Their impeccable menu takes the intimidation out of ordering bottles by describing juice with helpful, if a little tongue-in-cheek, designations like “fruit-forward and frisky,” “rich, bold and ‘intellectually satisfying,’” and “interesting and potentially funky.”

While not technically a bar, Old 502 Winery—the city’s first and only urban winery—deserves a visit. Onsite tastings are only $10 and include six wines; you can play it safe with choices like the Kentucky Lady, a refreshing and sweet white made from all Kentucky fruit, or go a little funky with the Bourbon Barrel Red, a semi-dry red wine with a hint of that other famous Kentucky beverage.

Having a beer at Holy Grale is a religious experience, as the offbeat gastropub with a long, rotating list of local and craft brews is housed in an early 20th century Unitarian church. Explore the choir loft or biergarten with a pint in hand. Beware, however—if you are looking for bourbon or wine, there is none to be found here (however with 26 taps and killer chicken gravy poutine, you won’t miss it).

For something with a little less saintly backstory, head to Meta, a downtown bar that used to be the Show-n-Tell strip club; though it is looking decidedly more posh now. According to co-owner Jeremy Johnson, the drink menu is inspired by the meta elements of historic cocktails—how different drinks were reimagined over the course of decades by individual bartenders— and their bartenders have continued the tradition by serving up fresh craft cocktails that playfully reference the classics. Part-speakeasy, part-hipster hangout, this is the place to be past 1 a.m.

The now 92-year-old historic hotel is the essence of quintessential Kentucky charm. Ideal for Derby-time visitors, it’s the place to go classic with a Brown Manhattan, Old Fashioned, or a Kentucky Derby (Four Roses, sorghum syrup and pink grapefruit juice).

Drink surrounded by contemporary artwork at Proof on Main, the bar within hip 21c Museum Hotel. The stuff behind the bar is as carefully curated as what is hanging on the walls; Proof’s spirit collection emphasizes small batch, artisanal craftsmanship from around the world, and fresh juices, inventive infusions and house-made tonic are highlights of their signature offerings.

Head down to The Cellar at Decca for cocktails with a focus on fresh and house-made ingredients, which pair well with the upscale bar bites. Think farmstead cheese board and shoestring frites. Decca is locally known for its music: live jazz, vinyl, or sounds from the vintage jukebox set the mood; though perhaps the bar is even more infamously known for its $5 Holla—Shot of Bourbon and a can of beer deal.

You can’t come to Louisville without going to a bourbon bar, and Down One is the ultimate. Located on historic Whiskey Row, right in the heart of downtown, this bar stocks over 160 bourbons. Enjoy on the magnolia tree-lined patio (or see if you can find the secret Prohibition-style phone booth room stocked with some of the rarest bourbons available).