Gathering up your best friends and working your way through a series of bars is one of the best ways imaginable to spend a summer evening out. You get great company, you have the chance to sample drinks from a variety of creative minds, and there’s an air of spontaneity and seeing where the night takes you that’s truly intoxicating. Three wins.
Oh, and also the intoxicants are intoxicating. Meaning you get drunk. Which can be pretty damn fun with the right crew.
When deciding to take a crawl, there are two important questions to ask yourself: 1) Is my destination highly walkable? and 2) Is the neighborhood dense with pubs and bars? Some maniacs will insist that ride-sharing services have made the first question irrelevant. They’re wrong. It’s always better to walk a few blocks in the night air than it is to wait 20 minutes for a dude in a Toyota Corolla to pick up your wasted posse. This is supposed to be an odyssey, after all.
The list below features some stone-cold classics, a few up and comers, and a curveball or two. Each crawl highlights an awesome neighborhood — where you and your friends easily keep yourselves entertained without having to trudge ten miles to do so. If you really crave the cardio, you can always walk home.
Williamsburg — New York, New York
We know Williamsburg has come to be associated mostly with the hipsters who moved in and spurred the gentrification of this neighborhood, so you’re more than welcome to balk at our suggestion on the grounds of fixed-wheel bike and beard fatigue. But the tiny tattooed, placebo lens bespectacled residents have launched some great bars and breweries in a very compact area and you can get to them with a quick L train jaunt to Bedford, making this a great place to get very drunk.
For sure hit George & Jack’s Tap Room, a little pub that has local dive vibe — don’t miss the chance to play some indie music or punk on the jukebox. Hit Gutter Bar to continue the grungy feeling with a side of bowling in one of the eight vintage hardwood lanes. And be sure to stop into The Gibson, where 100 styles of whiskey grace the menu and fine craft beers are always in rotation. If you’re willing to walk a little out of the way, Barcade is definitely worth a visit. This bar/arcade combo gives you a chance to enjoy shots and games like Joust and Centipede together, a trend which the team here takes credit for starting. There are so many other bars dotted between the few mentioned above that listing them would spoil the adventure, feel free to pop into whichever strikes your fancy. Brooklyn Brewery and Dardy Bar are particularly fun, but the likelihood of going wrong here is slim.
If you spend the night in Williamsburg, know this: hipsters may be annoying, but they’re f*cking fantastic at making superb coffee and hangover killing brunches.
French Quarter — New Orleans, Louisiana
Many people (who don’t live in New Orleans) hear “French Quarter” and immediately think “Bourbon Street.” This is fair enough — especially when it comes to a good, old-fashioned bar crawl. Why not stumble along beside drunken tourists, trailing a Second Line, crisscrossing the street to visit various bars and strip clubs? That’s an easy recipe for a raucous night, right there. But if you crave something quieter, and something that more resembles a local experience, venture away from Bourbon Street and you’ll find a smattering of more intimate bars serving craft cocktails, pubs that have hosted the neighborhood locals for century or two, and some gritty dives that will help you get a better sense of NOLA.
You’ve probably heard about Pat O’Brien’s for the signature Hurricanes they first crafted in the 1940s, but if you want a good rum cocktail you’ll probably have a better time in one of the Tiki bars on a single block of N. Peters St. Or hit both; few things are as fun as a Tiki bar. Tiki Tolteca is a Latin-infused option above a Mexican restaurant, and Beachbum Berry’s Latitude 29 is the baby of cocktail guru Jeff Berry located in the Bienville House Hotel. Aunt Tiki’s is worth a visit too, but don’t expect a Tiki bar. This is more of a Halloween-themed dive where you can grab cheap drinks from a tattooed bartender and enjoy them with a minimal number of tourists.
If what you crave is a really good cocktail, Bar Tonique was once of the city’s first craft cocktail bars and has the feel of a classic local dive. If you’re looking to sip your drinks in a more upscale setting, we’d suggest Longway Tavern (which also serves excellent food; get the chicken sandwich and/or the Caesar salad) or Cane and Table (if you’re feeling adventurous, order “a pineapple” — the bartender will take it from there).
In the realm of dives, it’s hard to beat Harry’s Corner, Molly’s at the Market, and the Chart Room. We’d put all three up against any dives in America. Oh, and Santos is a great option if you’re looking for a dive where you can also catch a performance by a punk band.
The Tenderloin — San Francisco, California
Everyone knows that The Mission is probably the best place to drink in the city, but we want to turn your attention to The Tenderloin — which doesn’t get as much fanfare because of its large homeless population and the off chance that you could have your cell phone stolen or your car burgled. Trust us: as long as you don’t get blackout drunk and you remain aware of what’s happening around you, you can totally enjoy this culturally and historically rich neighborhood in the heart of the city just as safely as you can any other part of SF.
There was a time before gentrification that this neighborhood had an excellent whiskey bar. Though we mourn the loss of Whiskey Thieves, we celebrate Whitechapel — a gin bar with the largest selection on the continent. We can’t get enough of this gin lover’s steampunk daydream. And though we fully realize the shark has well and truly been jumped on speakeasies, we still love 1920s-style speakeasy Bourbon & Branch and the secret speakeasy hiding inside of it, Wilson & Wilson. It’s a little complicated, but suffice to say there is a faux detective agency and you enter the bar through its bathroom. Then, you order elaborate drinks made with infused spirits and house-made tinctures.
Rainey Street — Austin, Texas
For people looking to make the most of walkability and drinking establishment variety in Austin, Rainey Street is a dream. This tucked-away street is home to renovated houses that have become bungalow bars, and tourists and locals alike enjoy strolling through the compact neighborhood to chill at some of the best bars in the city. Plus, the abundant food trucks don’t hurt. Nothing is better after a night of drinking.
If you aren’t looking to quaff cocktails all night and instead want to stick with beer, Bangers Sausage House & Beer Garden has over 100 beers on tap. If the weather is good, take things to the outside seating area and go full beer garden. If you only want Texas beer, check out the 51 local taps at Craft Pride. However, those jazzed about mixology need to hit Half Step for a casual cocktail made with the best ingredients. We also like the divey Clive Bar with its sense of humor. They make a “Matthew Pecanaughey” — a bourbon Old Fashioned made using housemade pecan syrup bitters. Yums.
Fans of mezcal will head for the little stone house behind Clive Bar to enjoy Bar Illegal, a bit of a secret that only serves Victoria beers and drinks made with Illegal Mezcal.
Hampden — Baltimore, Maryland
When it comes to Baltimore, Fells Point really comes correct with bars, but we like the funky Hampden neighborhood with its kitschy boutiques, awesome places to drink, and iconic locations from John Waters films. Plus, 36th Street, or “The Avenue” as it is called, keeps everything walkable.
Start the night early by stopping in at Eightbar, the bar that is inside Atomic Books. The bookstore itself bills itself as “Literary Finds for Mutated Minds,” and it’s where John Waters receives fan mail, so we can’t think of anywhere more fun to start drinking. Be sure to visit The Bluebird, which has both an upscale cocktail room and a cozy and subterranean pub. Keep the blue theme in place with a stop in at Blue Pit BBQ & Whiskey Bar, where you can get a signature cocktail or turn any of their many whiskeys into a classic drink for a few bucks. De Kleine Duivel, a Belgian beer hall, is well worth a stop, as is Frazier’s on the Avenue — a huge ass space with two bars and a rad jukebox.
Downtown — Orlando, Florida
It’s pretty easy to get caught up in the theme park aspects of Orlando, but locals know that downtown has a lot of charm. There’s a really cool performing arts and museum scene, and though when it comes to bar crawls, the area is a bit more quantity than pure, bartender-driven quality, there are plenty of really solid options that are unique and unforgettable. Plus all that competition leads to cheaper drinks.
It’s best to hit the craft cocktail spots early on for a few reasons. Firstly, once you are buzzed, you won’t be able to appreciate the mixologist’s skill quite as well. Second, these places get more densely packed the later it gets. Make Hanson’s Shoe Repair or The Courtesy your first stop. The former requires a password and the latter has the honor of being the first real cocktail bar in the city. You can avoid crowds by getting into The Woods where they keep a strict cap on guests. Plus, they do happy hour all night long. Get a pudding shot at Lizzy McCormack’s Irish Pub. Finally, be sure to hit The Lodge — a divey Christmas themed bar with a photo booth to document your rager.
Downtown — Detroit, Michigan
Detroit had a fallow period when buildings lay vacant and were for sale at greatly decreased prices. Young creatives looking to take these abandoned spaces and use them to realize dreams started buying them up, and now the city is one of the most interesting in the country. That’s certainly true for galleries, restaurants, and confectionaries. But it’s also true of bars.
No bar crawl in downtown Detroit should be undertaken without stopping in at Standby, a creative, consistent, and eminently satisfying cocktail bar. Try the Belladonna made with Moletto tomato gin, St. George green chile vodka, Ancho Reyes, corn cob, lime, and pickled tomato. Then go down the alley to the Standby’s sister bar The Skip where people get bomb tropical cocktails and frozen drinks like cucumber margaritas. Occasionally, the entire alley between the two gets shut down for concerts and events. Also stop in The Oakland, which calls itself an “art novelty company” and serves imaginative cocktails that highlight a variety of spirits purchased abroad. If you want a drink you can’t get anywhere else, this is the place to go.
Strip District — Pittsburgh, Pennsylvania
Like all the cities featured here, Pittsburgh has multiple neighborhoods and streets that make for an ideal bar crawl. We favor The Strip because we like food when we drink and the Strip District is one of our favorite places to eat in the city. It’s also home to some really interesting bars and nightspots.
If you like rum, then Maggie’s Farm Rum Room is a great place to begin your crawl. The folks on the Allegheny Distilling team — makers of the beloved Maggie’s Farm Rum — fill their menu filled with rum twists on classics and tiki drinks that take full advantage of their tasty spirits. Be sure to stop in at Bar Marco, a cocktail and wine bar housed in a historic firehouse. The menu is small but tasty and this is one of the few restaurants in the city to go tip-free. Then make your way to the Wigle Whiskey distillery and tasting room before it closes at 10 pm. You’ll want to work through a variety of organic grain-to-bottle tastings.
Richmond — Portland, Oregon
Portland has grown and changed dramatically over the last decade and though many people think the dream of the 90s is alive in this Pacific Northwest city, there’s less and less evidence to be seen. The dream of gentrification though is pretty clearly alive in Portland, which means neighborhoods that used to be ignored by local government are now full of condos and Blue Star Donuts locations. Richmond is just such a hood.
We’ve watched the businesses along Division change pretty dramatically over the years, but a few of the classic bars remain. This is why we think this is one of the best bar crawls; it combines shiny new places with some old dives. For sure go to Tom’s Bar and play some skee ball. This establishment makes a good stop with revelers walking west until they hit Reel M Inn, another old school dive bar in the area. In between, check out the Cat’s Paw Saloon, owned by former pro skater Mickey Reyes and covered in cool art and woodgrain. Stop in at The Richmond Bar for hip, modern surroundings and some killer signature cocktails like the Beet Down, a blend of gin, beet juice, lime juice, and simple syrup.
For food, consider popping into Olympia Provisions Public House and grabbing some drinks to wash down your wurst (or vegetarian platter).
Wrigleyville — Chicago, Illinois
When it comes to finding the largest cluster of bars in the city, the stretch of Clark from Belmont past the field to Grace Street is a serious contender. Trying to negotiate the crowds late on a Saturday night or during a Cubs game is an exercise in patience. And if you’re looking to get a little rowdy, the throngs of post-grad 20-somethings who still have the glow of youth and ride or die Cubs fans make for excellent companions. But be prepared for a lot of sports bars.
You have to make a stop at the Gingerman Tavern (or the Gman as it’s known). It has a local pub feel over a sportier one. And the bartender-operated jukeboxes are a nice touch, but be sure to bring cash. The Old Crow Smokehouse has a prevailing country theme that’s a nice break from all the Cubs memorabilia everywhere else. Think mason jars and a whole lot of whiskey. If you want to experience your favorite sports to the tune of 52 big-screen TVs, Casey Moran’s makes a nice bar crawl stop. And it’s huge. There are five fully stocked bars, a rooftop garden, a café, and a VIP lounge. Another large and in charge option is Sluggers, a bi-level bar with literal batting cages in it. There’s also trampoline basketball and dueling piano bar. It’s a really unique spot.