Sophisticated? Spirited? A smidge unruly? Whether you’re looking for something contemporary and composed or you’re looking for laughs, Chattanooga has an evening itinerary for your next guys’ night out.
Bridge Views and Vapors:
Whiskey Thief to Chattanooga Cigar Club
Chattanooga’s first rooftop cocktail lounge, Whiskey Thief offers perhaps the most beautiful view of the Walnut Street Walking Bridge and Tennessee River in town. Garden & Gun magazine named this place one of the best new bars in the South back in 2019, asserting, “The space has a fun, boho industrial vibe, with soaring windows, and the drinks are as well made as the vintage-style glassware in which they’re served.” Positioned atop The Edwin Hotel with more than 100 kinds of whiskey on-site, Whiskey Thief is named after one of the master distiller’s most critical tools. The menu also includes house whiskeys like the Real Baseball (a peanut butter-infused belle meade bourbon Italian liqueur) and classic cocktails like the New York Sour and Double Malt Old Fashioned. If you’re up for something special, order from The Lockers, where you’ll find a Yamazaki 12yr from Japan and a Macallan 18yr Triple Cask from Scotland. From there, head to Chattanooga Cigar Club, open until 2 a.m. on Fridays and Saturdays, where you’ll find premium hand-rolled cigars from around the world, plus a hookah lounge. Here, the menu includes smoked wings, fried okra, and mozzarella sticks. There’s a dress code for entry, so no sagging clothes, crocs, or backwards-facing caps. To guarantee good seating, booth reservations are available online.
A Speakeasy and a Crude Card Game:
Unknown Caller to Jack Brown’s Beer & Burger Joint
The door to Unknown Caller (formerly London Calling) is literally a red British-style phone booth on Cherry Street downtown. You’ll walk through a tight hallway with a phone on the wall, and if you dial the correct code, you can get in. On the other side is a bar inspired by the Prohibition era with high ceilings, jazz tunes, deep U-shaped banquettes, and low lighting. Outdoors on the patio bar, which was added in May 2021, you’ll find retro hip hop music and maybe even some bubbles and beer pong. “Imagine listening to ‘Waterfalls’ by TLC, whilst petting a stranger’s dog and chugging frozen Piña Coladas. That kinda vibe,” Unknown Caller posted to social media to celebrate opening night in the alley. This is the kind of bar where you can buy a microwavable cup of Kraft Mac and Cheese once the drinks weaken your decision-making. If that won’t do it, there’s always the M&M ice cream sandwich. If you’re the competitive type and up for a night out early in the week, finish your evening with a round of Cards Against Humanity at Jack Brown’s Beer & Burger Joint on Mondays from 9 p.m. to 11 p.m. Prizes are given out for 1st, 2nd, and 3rd place, and you’ll want to come with pals who can handle a little profanity and sexual innuendo – this is a game for adults. Stack your team with as many guys as you like, but know that table sizes top out at six chairs. Jack Brown’s also hosts trivia night on Tuesdays.
Big Laughs, Big City Style:
Carpetbagger’s Comedy Night
Comics from New York City join regional talent for Carpetbagger’s Comedy Night on first and third Friday nights at Bode Chattanooga. Hosted in the lobby by Jeff Greenspan, who moved to Chattanooga from New York City in the summer of 2020, the evening begins with Happy Hour at 8 p.m. and a comedy show at 9 p.m. Show tickets cost just $8 and include a beer, but you’ll need reservations to secure your spot. The Carpetbagger’s Comedy Night August lineup includes Ian Aber, who has opened for Fortune Feimster and Margaret Cho, as well as Brooklyn-based Michael Terry, who has performed at New York clubs like The Grisly Pear, Dangerfield’s, and Stand Up New York.
Bar Hopping with a Boozy Leg Workout:
Pints and Pedals
Pints and Pedals is the ultimate evening tour of downtown Chattanooga that encourages you to bring your own beverages on board, rag on the guys in your group for not putting in more of an effort, and hook up your own phone to the bluetooth speaker for control of the playlist. Here’s how it works: Decide whether you want to reserve a handful of public seats or go ahead and rent the entire bike for a private party (8-30 people). Meet at The Moxy hotel to begin the two-hour ride. Bring your own alcohol from home (no glass) to put into the cooler on the bike. For your pal who wants to ride along, there are a few non-pedal seats on board. Don’t be intimidated by the idea of exhaustion – electric motor assistance makes pedaling easy, but you do have to help! You can pick what bars you stop at or simply trust the tastes of your guide. Popular stopping points include Hi-Fi Clyde’s, Fountainhead, Sing It or Wing It, Southside Social, and Backstage Bar. At each stop, you’ll need to finish the beverages you purchase on-site before returning to the bike. And pace yourself! Nobody wants to end a guys’ night out pulling the dead weight of his friends.
Spirit Stills and a Progressive Meal:
Gate 11 Distillery to Station Street
If you’re into engineering and want to see the science behind the stills custom-built into the small spaces at the Chattanooga Choo Choo, start your night with a distillery tour at Gate 11. A microdistillery and bar, this place operates a pot still for whiskey, column still for vodka and gin and rum base, and glass reflux for botanical extracts and spirits fractionation. Be sure to also ask to see the Whiskey Boxcar. Distillery tours are available throughout the week, but the ideal time for kicking off a Chattanooga guys’ night out is Saturdays at 4 p.m. and 5 p.m. The tour includes a tasting of award-winning gin, rum, absinthe, vodka, and whiskey. Afterwards, there’s no need to move your car because Station Street on Chattanooga’s Southside is an ideal spot to park in one place and walk among a dozen places for food and drink. For your appetizer, stop by STIR for in-season oysters shipped from the Eastern seaboard, Gulf of Mexico, and waters of Canada and the West Coast. Next, walk to The Terminal Brewhouse for the pot roast nachos or a 6-oz. bison burger paired with a Monk’s Wages Belgian Pale Ale. For after-dinner drinks and live tunes, you can bounce back to Gate 11 Distillery or walk to Westbound Bar, which has live acoustic music on Fridays and line dancing lessons on Saturday nights. If you need to pop in somewhere for dessert, Clumpie’s Ice Cream is on the corner just past the Kinley Chattanooga hotel.