Robert Harding World Imagery / Alamy
Samantha DiMauro
October 22, 2014

Of all the historical sights to see in Boston, some of the best are the ones that offer ice-cold brew and an indulgent meal along with great photo ops. If you want to savor the taste of times past, why not do it by kicking back in Babe Ruth’s onetime local watering hole? Or lingering in the Union Oyster House, open since 1826, where local luminaries once dined in between planning the Boston Tea Party, building America’s first subway system and publishing first editions of The Boston Globe? Many of the city’s centuries-old downtown dining rooms and wooden bars have been perfectly, ethereally preserved (and latter-day landmarks include the cramped kitchen where food critics from The Boston Globe and Wall Street Journal say the “best burgers in America” are flipped). So pull up an antique bar stool at one of these venerable spots, and ask the bartender for a story along with your pint. 

Union Oyster House

The oldest restaurant in Boston (which is on the National Register of Historic Places) jumped on the 19th-century oyster craze long before any other raw bars in the city even existed. The place, whose wooden floors, booths, and ceiling rafters are all original, has a history of catering to famous politicians, like Civil War-era senator Daniel Webster. On the second floor you’ll find a booth dedicated to former regular JFK.

Marliave

The fourth-oldest restaurant in Boston was built on Bosworth Street in 1885, and the moody lighting, white marble bar and tiled floors haven’t changed much since. The glassed-in rooftop patio makes a perfect setting for a romantic evening, especially during the 4:00–6:00 p.m. happy hour when the bar shucks $1–$1.50 clams and oysters.

McGreevy’s 3rd Base Saloon

This is what happens when Red Sox fans take over a traditional Irish pub. In 1894, it was the place to be for both ballplayers (including Babe Ruth), politicians (like Mayor John Fitzgerald, JFK’s grandather)—along with gamblers and the die-hard fan club known as the “Royal Rooters.” Today it’s known as the birthplace of Red Sox Nation, America’s first sports bar, and home of the American-Celtic punk band, the Dropkick Murphys.

Mr. Bartley’s Gourmet Burger Cottage

A Harvard landmark since 1960, this no-frills burger joint isn’t glamorous, though it has made Hollywood cameos in both Good Will Hunting and The Social Network. Patties come in pop culture-inspired flavors, like The Taxachu$ett$—topped with Boston baked beans, sriracha, bacon, and a fried egg—and have been widely touted as the best burgers in the country.

Jacob Wirth

Marked by a large, vintage clock suspended over the door, this legendary German beer hall’s antiquated facade stands out on the border of Chinatown. Opened in 1868 by bold businessman Jake Wirth, it was the original bar to pour Anheuser Busch beer, and today maintains its reputation for serving authentic German and Belgium drafts.

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