Picture the introduction to the sitcom “Cheers,” a montage of sepia-toned images of people throughout the 20th century packed into saloons and barrooms to raise a glass.

In an era where remote work, online shopping and restaurant delivery have made it easier than ever to never leave the house, going out for a drink feels like one of the last acts of civic congregation. Even if you’re not on a first-name basis with fellow patrons and the barkeep like the characters on the show, there’s something comforting about bellying up to the bar — either with friends or in the company of complete strangers and a good book.

For my money, there’s added enjoyment in imbibing in a place where drinking has gone on for decades, even centuries, adding to the sense of stepping out of your own life, if just for a couple hours, and sharing in the same ritual as bargoers of the past.

Given that Maryland is one of the oldest states in the country, an untold number of bars occupy historic buildings. Here are some of my favorite watering holes with a sense of history, with a focus on those that were purpose-built as bars and restaurants.

The Baltimore Banner thanks its sponsors. Become one.

The Belvedere Hotel
The Belvedere Hotel building, home of The Owl Bar. (Nick Thieme)

The Owl Bar

1 E. Chase St., Baltimore

Housed in what was once the Hotel Belvedere, the Owl Bar looks much as it did when it opened in 1903. The big, open room with tall brick walls, intricate latticework, hunting trophies and a long wooden bar is a grand space befitting the majestic beaux arts-style hotel. Leaded glass windows above the bar depict the namesake bird and the first three lines of a 19th-century nursery rhyme: “A wise old owl sat in an oak / the more he saw the less he spoke / The less he spoke the more he heard / why can’t we all be like that wise old bird?”

The urban legend is this was included as a nod to the establishment’s status as a wet bar during Prohibition. Thirsty customers who were in the know would look to the owl statues behind the bar: If the eyes blinked, there was fresh booze in supply; if they steadily glowed, the latest shipment had not arrived.

When it was still in operation, The Belvedere hosted many famous guests — their photos line the walls leading up to the bar’s entrance — and the Owl Bar was a favorite haunt of F. Scott Fitzgerald during his time in Baltimore.

Middleton Tavern in Annapolis, MD.
Middleton Tavern in Annapolis. Horatio Samuel Middleton constructed the Federal-style building near City Dock around 1754 as a tavern and boarding house. (Brandon Weigel/The Baltimore Banner)

Middleton Tavern

2 Market Space, Annapolis

The Baltimore Banner thanks its sponsors. Become one.

Horatio Samuel Middleton constructed the Federal-style building near City Dock around 1754 as a tavern and boarding house, according to records from the Maryland Historical Trust, the state’s historic preservation agency. Middleton also operated a ferry to Kent Island and Rock Hall on the Eastern Shore. Founding Father Thomas Jefferson stopped at the tavern, and it’s believed James Monroe visited in the early 1800s while he was the sitting president.

Over the ensuing centuries, the space was used for different functions, including as a commercial store and hotel. But in 1939, it was renovated to once again serve food and drink, and customers have dined in Middleton’s cozy rooms ever since. Jerry Hardesty bought it in 1968 and helped popularize Middleton Tavern’s oyster shooters ($2), a mix of one freshly shucked oyster, cocktail sauce and vodka. He died in 2021.

While much has almost certainly been added or subtracted from the Middleton’s interior over the years — it was damaged by fire in the 1970s — the tight spaces, fireplaces and mounted antiques, many of which nod to the Annapolis maritime heritage, preserve an ambience that feels frozen in time.

Built circa 1747 (hence the name) on land owned by neighboring St. Anne’s Church, this two-and-a-half story, five-bay Georgian building started out as an inn, hat shop and tavern named the Beaver and Lac‘d Hat operated by William Reynolds (Brandon Weigel / The Baltimore Banner)

1747 Pub

7 Church Circle, Annapolis

Built circa 1747 (hence the name) on land owned by neighboring St. Anne’s Church, this 2 1/2 story, five-bay Georgian building started out as an inn, hat shop and tavern named the Beaver and Lac‘d Hat operated by William Reynolds, according to the Maryland Historical Trust. After turns as a bank and library, the building was restored to its original use in the 1980s. Since 2000, Jill and Andrew Petit have owned the Reynolds Tavern, which is open for lunch and traditional English tea on the main floor and has lodging on the upper floor.

The Baltimore Banner thanks its sponsors. Become one.

In the dimly lit basement, though, is a small bar pouring craft beers and cocktails with only a handful of stools. The rooms are pretty bare-bones, and that’s part of the charm. When you duck down into this cellar and see the brick floors, low ceilings and visible wooden beams, walk-in fireplace, exposed bricks, and cream-colored walls, it feels like you could hunker down with a beer and hear the echoes of a long-gone conversation about “revolution.”

Italian immigrants Frank and Mary Victoria DeSantis Sr. opened this small bar in the basement of their home in 1933. (Brandon Weigel / The Baltimore Banner)

Venice Tavern

339 S. Conkling St., Baltimore

Italian immigrants Frank and Mary Victoria DeSantis Sr. opened this small bar in the basement of their home in 1933, after the end of Prohibition. A poster of former President Franklin Delano Roosevelt, who oversaw the passage of the Cullen–Harrison Act legalizing the sale of low-alcohol beer and wine and then the 21st Amendment fully repealing Prohibition, still hangs above the bar as a paean to the leader who brought back legal booze.

His is not the only historic likeness, as images of old prizefighters also decorate the walls. Another great feature, which you can see in any number of Baltimore buildings, is the pressed tin ceiling, though the one here is low enough to inspect up close. What really makes the Venice Tavern stand out is how small and intimate it is — after all, it’s in a former basement. Yes, there are modern creature comforts like TVs and a wall-mounted jukebox, but those don’t take away from the aura that comes with having a drink in this quintessential neighborhood dive.

The Valley Inn restaurant and bar traces its roots to 1922, but the history of the 2 1/2 story stone building goes back almost a century before that, when it was known as the Brooklandville House. (Brandon Weigel / The Baltimore Banner)

The Valley Inn

10501 Falls Road, Timonium

The Baltimore Banner thanks its sponsors. Become one.

The Valley Inn restaurant and bar traces its roots to 1922, but the history of the 2 1/2 story stone building goes back almost a century before that, when it was known as the Brooklandville House, according to the structure’s nomination form for the National Register of Historic Places. John R. Gwynn opened a tavern in 1832 near the crossing of the Baltimore and Susquehanna Railroad — a former station dating to 1905, which is now a private residence, sits across the street — advertising to would-be customers that “every attention shall be paid by his servants and himself to those that may honor him with a visit.”

Under owner John Hatfield Sr., the Valley Inn became a mainstay among residents in Green Spring Valley, while also drawing bold-faced names such as Fitzgerald, Harry Truman, Clark Gable, H.L. Mencken and Alfred G. Vanderbilt as guests.

Vanderbilt, the former owner of Sagamore Farm and Pimlico Race Course, is of particular resonance here, as the Valley Inn continues to embrace the area’s equestrian heritage with art and artifacts on its walls. While highways and development around Green Spring Station have made this a more bustling area, and the restaurant has seen modern additions, such as an outdoor patio with live music and corn hole, the wood-paneled walls of the bar and dining rooms harken back to the Valley Inn’s roots as a secluded countryside destination. The kind of place you’d go for a few cocktails after a long day of riding.

More From The Banner