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Destination Drinking: 8 Can't-Miss Bars and Fests For Your 20s

This is your decade of prime honky-tonkin’. Which is why we recommend that you make it to as many of these legendary bars and festivals as possible.

Gordy Megroz
(Krivosheev Vitaly)
road trip drinking festivals best festivals destinations best road trip destinations

Your Ultimate Road Trip

This is your decade of prime honky-tonkin’. Which is why we recommend that you make it to as many of these legendary bars and festivals as possible.

Gordy Megroz

Poor Monkey Lounge, Merigold, Mississippi

A ramshackle hut in the middle of Mississippi farm country, 70 miles from Memphis, Po’ Monkey’s, as it’s more commonly called, is one of the last authentic juke joints in the South. While the structure and ambiance haven’t evolved much over the years—it still looks like something out of Beasts of the Southern Wild—the hours and musical tastes have: the bar is now open only on Thursdays, when a DJ spins dance music for a crowd of mostly young locals and (possibly bummed) blues pilgrims. Beer, soda, and bottled water are the only official items on the menu, but BYO liquor is allowed.

poor monkey lounge mississippi drinking destinations road trip rap music
(Ken Murphy)

The Desert Bar, Parker, Arizona

Technically, it’s the Nellie E Saloon, but because it’s located off the grid (no phone, solar power), on the edge of the Sonoran Desert (about 15 minutes down a dirt road outside Parker), people just call it the Desert Bar. What opened in 1983 as a three-sided shack has since grown into a sprawling, five-building compound, with an outdoor eating area, a stage, two large evaporative-cooling towers that provide air-conditioning, and even a church (mostly used for weddings). The odd mix of locals, tourists, and Mad Max ATVers (mountain biking here is also an option) creates a Burning Man–like atmosphere every weekend from October to April, noon to 6 P.M., when Ken, the owner, kicks everybody out before things get totally out of control.

desert bar church parker arizona drinking road trip
(Melissa Wright)

Lander Bar, Lander, Wyoming

Although there are still remnants of the brothel that occupied this building 100 years ago (bullet holes in the tin ceiling, ancient liquor bottles, a pair of women’s shoes), most of the the Lander Bar’s decor reflects its current patrons—climbing and mountaineering gear (National Outdoor Leadership School has its headquarters in Lander) and cowboy paraphernalia (cattle, sheep, and hay production remain the backbone of the region’s economy). After you’ve spent a few days climbing, backpacking, or fly-fishing in the nearby Wind River Range, the locally sourced Muy Bueno Burger and Lander Brewing Company’s Jack Mormon Pale should taste especially good. Bluegrass music usually starts around eight.

lander bar lander wyoming hotel destinations road trip drinking
(Cameron Maier)

The Tourist Club, Mill Valley, California

When we e-mailed the San Francisco branch of Nature Friends to ask questions about the Tourist Club, a 100-year-old watering hole in the middle of the Muir Woods that the Friends maintain, they told us to go away. “Let’s do all we can to discourage publicity,” the international conservation group wrote. That just made us more eager to find out what makes this place so special. Maybe it’s the parties we’ve heard they hold each May, July, and September. Or the joint’s German brauhaus vibe. Or that its balcony peers off into a vast thicket of redwoods. The only thing we do know is that the private club is open to the public only a weekend or two every month (check the website) and that it’s reached by a 50-minute hike on the Dipsea and Sun Trails. We just hope it serves frosty pilsners.

the tourist club mill valley california road trip
(Paul Volk)

Outside Lands, San Francisco

Held in early August in Golden Gate Park, this newish gathering bills itself as “the world’s only gourmet music festival.” That’s probably not true, but the local food and drink is even more impressive than the musical lineup, which this year included Nine Inch Nails, Daryl Hall and John Oates, and Jurassic 5. Among the comestible offerings: Beer Lands, a big tent featuring 16 regional microbreweries; Wine Lands, an even bigger tent with samples from 32 California vine-yards; and Choco Lands, a Twizzler-gated area with everything from hot cocoa to chocolate-dipped Rice Krispies treats. Early August (so plan for fog and cold).

jack white third man records outside lands music festival san francisco 2012
(Tom Tomkinson)

The Hahnenkamm, Kitzbühel, Austria

Yes, we’re telling you to go to Austria to watch a ski race. To understand why, you first must know this: Alpine skiing is Austria’s national pastime. The Hahnenkamm, the most treacherous and famous race on the World Cup Alpine circuit, is its World Series. And for three days every January, Kitzbühel, an other-wise glitzy and charming town, becomes the site of the largest, rowdiest outdoor party in the ski universe, with some 70,000 rabid fans fueled primarily by local hefeweizen and homemade schnapps and currywurst. There are races all three days, and the Londoner, the town’s most famous pub, hosts a massive party after the men’s final on Saturday night. (You’ll need to be in line by 9 p.m. to get in.) January 24–26.

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FloydFest, Floyd, Virginia

If Bonnaroo and the GoPro Mountain Games had a baby, it might look like FloydFest. In addition to bringing in big-name bands like Edward Sharpe and the Magnetic Zeros and Old Crow Medicine Show—the four-day event in the Blue Ridge Mountains also hosts guided mountain-biking and paddling outings and a weekend-ending 5K trail run. Pitch your tent in the area known as Scenic Camping, where the short, steep hike keeps the masses away. Then grab a loaner bike from Starlight Bicycles’ pop-up shop and hit the Moonstomper trail, a twisty, mile-long ride under a canopy of oak. When the music starts, head to the Dreaming Creek Main Stage, a timber construction with views of the mountains. July 24–27.

floydfest music virginia dancing bands

Telluride Bluegrass Festival, Colorado

There are several reasons why Telluride, one of the West’s original bluegrass festivals, is still the best. For starters, while the actual bluegrass is world-class (Sam Bush, Béla Fleck, and Jerry Douglas play nearly ever year), it’s also a bit of a misnomer: recent acts have included the Decemberists, David Byrne, and Ryan Adams. And then there’s the setting: the festival coincides with the summer solstice, and the stage, inside Town Park, just off Main Street, backs up to the ski resort, offering endless views down Telluride’s spectacular box canyon. There are several large campgrounds where you can pitch your tent, but try to land a spot on the baseball diamond in Town Park, the only camping area inside the action. June 19–22.

telluride bluegrass festival music bands bands crowd
(Sierra Stafford/Flickr)

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