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Stop and Sip at These Iconic Bars

Your favorite brand of beer or bottle of wine may taste the same no matter where you drink it, but where you drink it definitely matters.

For travelers who enjoy a pint, a pour or a cocktail, happy hour can be the highlight of a day on the road. And although there’s nothing wrong with taking a load off in a hotel bar, a better way to go is to visit a legendary local drinking establishment.

At signature bars across the country, travelers can enjoy historic ambiance, handcrafted cocktails, live music and a sense of place unique to that destination. Here are a handful to keep on your radar as you plan adventures for your group of bon vivants.

Green Mill Cocktail Lounge


Visiting Chicago today, you’ll see virtually no evidence of the infamous organized crime families that ran the city’s underworld a century ago. But at the Green Mill Cocktail Lounge in the city’s Uptown neighborhood, travelers can drink much like Al Capone once did.

The Green Mill was first opened as Pop Morse’s Roadhouse in 1907, then renamed in 1910. Throughout the early years, it was frequented by actors and executives from nearby movie studios. Later on, during Prohibition and the heyday of the Chicago mob, the bar became a frequent haunt of Al Capone, whose favorite booth is still in the establishment. Hidden passages used to transport bootleg alcohol and evade police are still in the building as well.

Today, the Green Mill is a popular spot for live jazz, with live music every night of the week.

Tootsie’s Orchid Lounge

Nashville, Tennessee

If you’re a music fan, there’s a solid chance a trip to Nashville, Tennessee, is in your future. And if you enjoy a drink with your tunes, your visit might just include a stop at Tootsie’s Orchid Lounge.

Directly across the street from the famed Ryman Auditorium, Tootsie’s is one of several legendary honky-tonks on Broadway in the city center. The lounge is named for Hattie Louise “Tootsie” Bess, who purchased the lounge in 1960. Over the years, she served numerous then-unknown customers who would go on to become major stars, including Kris Kristofferson, Faron Young and Willie Nelson.

Today, the walls at Tootsie’s are lined with memorabilia and photos from the many notables who drank or played music there over the years. Groups that pay a visit can expect cold drink and high-quality live music seven days and nights a week.

Luckenbach, Texas

There’s only one place in America where the destination is synonymous with its signature bar: Luckenbach, Texas.

Popularized by a Waylon Jennings and Willie Nelson song in the 1970s, Luckenbach is a tiny town in the Texas Hill Country famous for the cold beer and live music served at its general store. Luckenbach was established as a trading post in 1849. That trading post grew to include a store and a dance hall that featured live country music every weekend, drawing visitors to the small community where “everybody is somebody.”

Groups traveling the area can enjoy these festive weekend dances or even catch performances from regional and national artists who stop to play Luckenbach on their tours. The general store offers a full food menu and a variety of Luckenbach-branded merchandise.


Pensacola, Florida/Gulf Shores, Alabama

Any decent oceanfront vacation destination in the United States is bound to have a good beach bar, but none is as unmistakable as the Flora-Bama.

Opened in 1964, the Flora-Bama sits precisely on the state line in the spot where Pensacola, Florida, meets Gulf Shores, Alabama. Visitors can literally purchase a drink in one state and then walk a few steps to a table in the other state to sit down and enjoy it. While there, they’ll enjoy beautiful views of the white sands and emerald waters of the Gulf Coast, as well as a helping of live music.

There’s plenty of space for groups to spread out at the Flora-Bama; the establishment features five bars and 40 restrooms. There’s also a full-service restaurant on-site. And while visitors can order just about any drink they like, the signature cocktail is the Bushwhacker, the house recipe for which is a closely guarded secret.

Saloon No. 10

Deadwood, South Dakota

Walking through the streets of Deadwood, South Dakota, it’s easy to imagine the gunfights that once took place in this rough-and-tumble frontier town. But for the most immersive Wild West experience, travelers should plan a stop at Deadwood’s famous Saloon No. 10.

For over 140 years, outlaws and travelers alike have sipped on whiskey and other drinks at Saloon No. 10. Notable patrons during the Wild West heyday included Doc Holliday, Buffalo Bill Cody, Wyatt Earp and Calamity Jane. The saloon was cemented in Western lore when lawman Wild Bill Hickok was assassinated during a poker game there in 1876.

Today, Saloon No. 10 bills itself as “the only museum in the world with a bar.” In addition to sampling one of 171 whiskeys and taking in the antiques and artifacts lining the walls, visitors can enjoy historical reenactments and live gambling at the saloon.

Historical Iron Door Saloon

Groveland, California

Most visitors to Groveland, California, come in search of outdoor experiences; the area is a gateway to the iconic Yosemite National Park. But once the sun goes down, many find their way to the Iron Door Saloon.

Constructed in the early 1850s, the Iron Door Saloon is known as the oldest saloon in California. The building was constructed with solid granite blocks and features a namesake iron door. It became a saloon in 1896 and has been a popular watering hole for locals and visitors alike ever since.

Customers stopping at the Iron Door today come for the drinks and the historic atmosphere. Bullet holes in the granite walls reflect the area’s storied past, and artwork and artifacts around the establishment pay homage to Yosemite’s stunning natural beauty.

Old Ebbitt Grille


The scene is de rigueur in any political drama set in the nation’s capital: D.C. power brokers meet after hours in an upscale bar and quietly hammer out a solution to a seemingly intractable problem. This trope is a case of art imitating life, and the bars depicted are often inspired by the Old Ebbitt Grille.

Founded in 1856, the Old Ebbitt Grille is Washington’s first known saloon. In its early days, the Ebbitt was a boardinghouse. Later, presidents such as Ulysses S. Grant, Andrew Johnson, Grover Cleveland, Theodore Roosevelt and Warren Harding stopped in for drinks and discussions at the Old Ebbitt Grille’s stand-around bar.

Today, the Old Ebbitt Grille is still a popular after-work stop for the capital’s who’s who. It’s also a great place for visitors to grab a drink, admire some memorabilia and enjoy some of the city’s best oysters.

McGillin’s Old Ale House


History is everywhere in Philadelphia, from Independence Hall to the Liberty Bell and dozens of other locations. History lovers and beer lovers visiting the city can keep the historic experience going during their downtime with a visit to McGillin’s Old Ale House.

Beer taps began flowing at McGillin’s in 1860, not long after the Liberty Bell cracked, and the doors have been open ever since, making McGillin’s the oldest tavern in Philadelphia. It celebrated its 150th anniversary in 2010, which earned it coverage in dozens of national media outlets.

Groups visiting McGillin’s can raise a glass to toast the nation’s history. The ale house makes a good stop for meals, too, offering a menu of classic American dishes, including the iconic Philadelphia Cheesesteak.

Brian Jewell

Brian Jewell is the executive editor of The Group Travel Leader. In more than a decade of travel journalism he has visited 48 states and 25 foreign countries.