There are plenty of ways to stave off the chill of a dark winter night, but among my favorites: ducking into a cozy bar for a quick drink, bite to eat and some time indoors.

Lucky for me, as someone new to exploring the historic streets of our state capital, Visit Annapolis & Anne Arundel County published a list of five destinations for a “Colonial Cocktail Crawl,” partially in recognition of next year’s 250th anniversary celebrating the founding of the United States.

In the order listed by the tourism organization, here are my impressions of each stop along the Colonial Cocktail Crawl.

Reynolds Tavern

Climbing down the steps off Franklin Street and into the basement bar at Reynolds Tavern felt like falling back through time. That makes sense — founded in 1747, the place has continuously been a popular gathering spot in town.

Advertise with us

I was drawn to the fireplace in the back, which is an original fixture from when the tavern was built (though it’s gas now, and not wood-burning). It gave the bar a gentle glow and warmth.

Stepping down the stairs and into the 1747 Pub at Reynolds Tavern feels like walking back through time. The fireplace is from the building's original structure, even if it's a gas fire now.
Stepping down the stairs and into the 1747 Pub at Reynolds Tavern feels like walking back through time. The fireplace is from the building's original structure, even if it's a gas fire now. (Cody Boteler/The Banner)

The cocktail crawl guide suggested sipping a rum punch or ordering an eggnog, though I did not see either listed on the menus. I went with a local beer, from Idiom Brewing, and enjoyed sipping quietly by the fire.

Middleton Tavern

When I sat at the solid wood bar under strung Christmas lights at Middleton Tavern, I got the same feeling you get when you go out drinking in your hometown with your pals from high school the night before Thanksgiving — and I mean that as a good thing!

The interior of Middleton Tavern in Annapolis is cozy, with wood paneling and a fireplace, and has a nice selection of beers on tap and fresh seafood.
The interior of Middleton Tavern in Annapolis is cozy, with wood paneling and a fireplace, and has a nice selection of beers on tap and fresh seafood. (Cody Boteler/The Banner)

Middleton Tavern, with Christmas music softly playing and its worn bar stools, felt like settling in with an old friend. Above me hung a beautiful chandelier that I imagined being lit with candles or oil lamps during the 18th century.

The guide told me Middleton Tavern serves “traditional Maryland fare,” and I was able to get tasty (albeit small) crab cake sliders along with a beer from Delaware-based Dogfish Head Brewery.

Advertise with us

George Washington, Thomas Jefferson and Benjamin Franklin are all said to have frequented Middleton, so happy-hour goers are in storied company when they raise a glass.

Harry Browne’s

Harry Browne’s felt like an odd addition to the crawl — it’s by no means a historic establishment. It does, however, have a stunning view of the State House, which itself is steeped in history — including, famously, Washington resigning his commission as commander-in-chief.

Harry Browne’s is fancy, the kind of place where you’re asked if tap water is OK and every table setting has a charger plate.

The guide said Harry Browne’s had an atmosphere “perfect” for sipping on bourbon cocktails, so I ordered an old fashioned, flavored with spiced pear for the holiday season.

Harry Browne's in Annapolis can boast a delicious holiday old fashioned flavored with spiced pear — and enviable views of the State House.
Harry Browne's in Annapolis can boast a delicious holiday old fashioned flavored with spiced pear — and enviable views of the State House. (Cody Boteler/The Banner)

Reader, it was delicious. The bartenders certainly know what they’re doing. An old fashioned is typically liquor forward, and this was no exception. However, the hot sting of bourbon was balanced with the sweetness of a dark, syrupy cherry and the warmth of cinnamon and other spices.

Advertise with us

Federal House Bar & Grille

Federal House is large, with a heavy-looking wooden bar and dark wood throughout. It’s from the 1830s — well after the “Colonial” period — but still rich with details that connect it to its past.

It’s near the water, which is a plus. Visit Annapolis suggested grabbing a seafood dish, so I ordered fish and chips. It was a bit pricey ($25) but the fish was moist with a tender flavor and delicate, well-seasoned skin.

A paper plane cocktail and serving of fish and chips at Federal House Bar & Grille in Annapolis.
A paper plane cocktail and serving of fish and chips at Federal House Bar & Grille in Annapolis. (Cody Boteler/The Banner)

I ordered a paper plane, which is a new-classic cocktail made of equal parts bourbon, lemon juice, Aperol and amaro.

Usually one of my favorite cocktails, I found this one to be a bit more bitter than expected.

I would not describe Federal House as having the cozy atmosphere of the other locations on this list — in addition to its gorgeous stone-topped bar, it also had lots of big screen TVs mounted on the wall and popular country music playing on the radio that I could easily imagine getting louder later in the night.

Advertise with us

There’s nothing wrong with it, but that’s not quite the vibe I imagined for a “Colonial” crawl.

The Drummer’s Lot at the Maryland Inn

According to local history, this is where Benjamin Franklin, John Jay and Thomas Jefferson celebrated in 1784 after the Treaty of Paris was ratified, recognizing the independence of the United States of America.

The Drummer’s Lot is tiny and tucked partially underground. It has a gorgeous old wooden bar, windows that look out on Main Street, and cute nooks and tables that would make for great spots to take a date.

The Drummer's Lot at Maryland Inn is where some Founding Fathers are said to have celebrated after the ratification of the Treaty of Paris. The hot rum punch is, according to the bartender, inspired by an old recipe belonging to Benjamin Franklin.
The Drummer's Lot at Maryland Inn is where some Founding Fathers are said to have celebrated after the ratification of the Treaty of Paris. (Cody Boteler/The Banner)

I had to try the hot rum punch, which the bartender said was based on an old recipe of Franklin’s. It was warm, served in a glass mug. Not too different than a hot toddy (those are whiskey-based, though), it had strong flavors of citrus, spice and a hint of vanilla. I also had an expertly crafted house old fashioned.

Two words of note before deciding to go here, though: They’re only open Wednesday through Saturday, so plan ahead. And, because of a quirk with licensing, the bar does not serve any food, including ice. Drinks traditionally served on the rocks are served with chilled stainless steel cubes to keep cold, instead.

It works, but if you’re counting on the ice to cut the liquor, you’re out of luck.