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Walking into a bar with a sign that says “Established in …” instead of ruby red ropes and flashy new interiors always makes me feel like I’m not just drinking a beer, I’m drinking in history. While every major metropolis has its “it” bars, nightclubs, and eateries to see and be seen in, there is something about drinking a cold ale surrounded by rich history that’s much more alluring to me.

Whether it’s the oldest bar in town, or the historic spot where great politicians, authors, and celebrities have tippled, these are a few of my favorite “old” watering holes that make me feel like I’m not so old after all … at least for a night.

Photo source: johnbarleycorn.com1. John Barleycorn
658 West Belden, Chicago, IL

John Barleycorn, the name a personification of alcohol, garnered its historical significance during Prohibition. In the 1920s, the rear dining room of the restaurant doubled as a Chinese laundry and a front for bootleggers, who could bring liquor through the laundry to the bar’s basement. Patrons would enter here too, and head upstairs to the saloon. Famous drinkers include the bank robber John Dillinger, who used his illicit earnings to buy rounds on the house. While the clientele may have changed and the bar expanded with two new locations, you can still get a drink and a meal in the original building, built in 1890, without having to enter through the basement.

Photo source: heinoldsfirstandlastchance.com2. Heinold’s First and Last Chance Saloon
56 Jack London Square, Oakland, CA

Jack London aficionados are well familiar with Heinold’s Saloon, which is referenced at least seventeen times in his memoir, John Barleycorn. London was friends with the bar’s owner, Johnny Heinold, and spent a good deal of time in the tiny wooden establishment, penning such greats as Call of the Wild and The Sea Wolf.

The name of the bar is due to its location, in the Port of Oakland. During the 1920s, it was the first and last chance for servicemen and ferry passengers to get a drink and the nickname stuck. While in the bar, you’re likely to feel tipsier than normal because the floors, made from an old whaling ship, are permanently sloped from the 1906 earthquake. There’s a full bar and a few beers on tap; on warm nights tables are set up outside to accommodate local drinkers, myself usually among them.

Photo source: wikipedia.com3. White Horse Tavern
567 Hudson St., New York, NY

While many bars have hosted their share of literary greats, the White Horse Tavern, open since 1880, has had many brilliant butts on their bar stools. Norman Mailer, Anais Nin, Hunter S. Thompson, Ginsberg, and Kerouac all drank there, though the most recognized regular patron was Dylan Thomas, whose photos grace the wood walls. Though it’s rumored that a heavy evening of whiskey drinking at the White Horse contributed to Thomas’ premature death (he was thirty-nine), one can’t say for sure. What is certain is that these days, you’re less likely to find a literary great and more likely to find a standard bar menu and stiff drinks.

McGillian's Olde Ale House4. McGillin’s Olde Ale House
1310 Drury St., Philadelphia, PA

McGillin’s, which opened for operation the same year Lincoln was elected president, is Philly’s oldest operating tavern. Originally owned by William McGillin, an Irish immigrant who raised his twelve kids above the bar, McGillin’s descendants still run it today.

A popular gathering spot then and now, the bar has hosted such patrons as Will Rogers, Tennessee Williams, and Ethel Merman. They have home brewed beers on tap and claim to be the best Irish pub in town.

Photo source: unionoysterhouse.com5. Union Oyster House
41 Union Street, Boston, MA

Opened in 1826 and designated a National Historic Landmark, the Union Oyster House is Boston’s oldest bar. I like to belly up to the semi-circular oyster bar for a brandy and a few plates of oysters, just as-story has it-the famous statesman Daniel Webster did. Another famous guest here was JFK, who obviously made more of an impression than I did as he has his own booth (#18), commemorated with a plaque.

Nowadays the oyster bar serves standard fare, like chicken wings and nachos, as well New England clam chowder and oysters galore-usually to fannypack-wearing tourists.

6. Musso & Frank Grill
6667 Hollywood Blvd., Los Angeles, CA

Opened in 1919, Musso and Frank is Hollywood’s oldest eatery, and as such, has had its fair share of famous diners and drinkers. Charlie Chaplin and Douglas Fairbanks used to eat here, and its location near the Writer’s Guild made it a popular watering hole for authors such as Faulkner, Fitzgerald, and Hemingway. Not much has changed in the interior of the restaurant and they’re still known for super dry martinis, tasty Bloody Marys, and Welsh rarebit.

Photo source: mcsorleysnewyork.com7. McSorley’s Old Ale House
15 East 7th Street, New York, NY

Beer, men, and a “be good or be gone” motto characterize McSorley’s, both then and now. Opened in 1854, it wasn’t until the 1970s that the bar reluctantly opened its doors to women, having to rebuke their philosophy of “Good Ale, Raw Onions, and No Ladies.” You can still get good ale, a bite to eat (more than just raw onions, too), and decide for yourself whether you agree with e.e. cummings, who describes the bar in his poem “I was sitting in McSorley’s as “snugandevil.”

8. Lafitte’s Blacksmith Shop
941 Bourbon Street, New Orleans, LA

Lafitte’s is sometimes referred to as the oldest continually operating bar in the United States, and while that claim is hard to verify, the building in which it is housed is indeed old-thought to have been built before 1772. Made a National Historic Landmark in 1970, it has a scruffy exterior and a candlelight interior, where a piano man plays the oldies.

Photo source: hoteljerome.com9. J-Bar at Hotel Jerome
330 East Main Street, Aspen, CO

Serving since 1889, the J-Bar is best known for the signature prohibition drink “Aspen Crud.” During the dry times, the bar was converted into a soda fountain, but those in the know ordered theirs “crud,” indicating to the bartender they wanted their milkshake with a couple shots of bourbon. Nowadays, the hotel and bar are anything but cruddy-the elegance, opulence, and highfalutin’ ways may make you pine for the days of yore.

10. Vesuvio
255 Columbus Avenue, San Francisco, CA

Located in North Beach and overlooking Jack Kerouac alley, Vesuvio has served its fair share of Beat Generation luminaries. Established in 1948, it hasn’t changed much since Kerouac, Neal Cassidy, and other artists, poets, and musicians frequented the place. Now you’ll find a nice mix of locals with a few tourists sprinkled about. A great spot to have a casual drink amidst the bustle of SF.

The are certainly many more historic spots to have a drink or five-finding them is half the fun.

Photos courtesy of
This article was featured on in July 2008. Reproduced with permission.

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