Where to Go for a Bar Crawl in Annapolis

by Jennifer Waldera on Apr 12, 2016 in Roundups

Once the weather gets warm, who wants to hunker down at just one bar? It’s time to bar hop (or crawl, depending on how much you drink).Typically, we talk about where to drink and bar-hop by the water in Baltimore, but it’s time to give some love to our sister city, Annapolis.

There is no shortage of spots to find to drinks in Annapolis, but here are a few of our favorites.
 
There is likely no better place to drink on the water in Annapolis than Pusser’s. To be fair, if you aren’t measured about your drinking, you could likely wind up in the water just off Pusser’s outside seating, given their low ropes along the edge of the deck, so it might be a better place to start than to finish. Pay no worry, though, and settle into the outside seating if you can (it’s likely the most coveted waterfront view in Annapolis) and order a Painkiller (which comes with tiered levels of liquor) while enjoying the view and the water lapping against the deck. (80 Compromise St.; 410-626-0004)

Red, Red Wine
There are plenty of overpriced bars close to this place, but this cozy bohemian spot is the place to settle in with knowledgeable bartenders. The ambiance is as perfect for a first date as it is for a lowkey wine tasting or cozy stop on a bar crawl. Indulge in their flights or take their recommendations. A wine and cheese pairing is a necessity here, and the staff will deftly guide you through it. (189 Main St.; 410-990-1144)

This is one of the diviest of dive bars in downtown Annapolis, and if you’re bar-hopping through Naptown, it’s necessary to stop here. They serve food well beyond the closing time of most bars in Annapolis, and it’s the most comfortable spot to settle into on West Street, with plenty of seats to accommodate the crowds and a wide variety of live music and other events, like beer dinners and tap takeovers. (37 West St.; 410-263-1993)
 
This somewhat hidden treasure is a quasi-basement bar located in the Maryland Inn and close to the circle. Be prepared to drink strong cocktails and be regaled with some haunted history of the hotel. Classic cocktails are the way to go if you’re not choosing a glass of wine from their impressive yet affordable list. (16 Church Cir.; 410-216-6340)
 
John Barry at O’Callaghan’s
This spot, located on the first floor of O’Callaghan’s Hotel, serves as both an ideal starting point or a nightcap-style spot. The Manhattans are on-point and the appetizers are some of the best stomach-liners before a night out. (174 West St.; 410-263-7700)

Photo via Flickr user m01229


Tags: Bar Crawl, Beer, Cocktails, Wine
Recent Articles
spacer

Feedback

How are we doing? Tell us what you like or don't like and how we can improve. We would love to hear your thoughts!

*Name:
*E-mail:
*Suggestions:
 
Shiner Beer Donates $100,000 to Hurricane Irma Relief

Shiner Beer Donates $100,000 to Hurricane Irma Relief

As hurricanes continue to devastate the US some breweries are helping out, including most recently The Spoetzl Brewery in Shiner, Texas. ...read more ›

by Alexander Frane Sep 19, 2017
Baltimore's Best Local Fall Beers

Baltimore's Best Local Fall Beers

As we work our way into the cooler months, it can be slightly more challenging to find a way to warm up with a quality local brew. Here, we have a few...read more ›

by Jennifer Waldera Sep 19, 2017
You Can Get Drunk on Popcorn Now, If You Really Want To

You Can Get Drunk on Popcorn Now, If You Really Want To

A U.K. based company is making alcohol-infused popcorn at 5% ABV, if you really feel compelled to get drunk off your movie snack....read more ›

by Ryan Hudak Sep 12, 2017
SPONSORED
Visit Drink Baltimore on Your Phone
Where to Celebrate Oktoberfest 2017 in Baltimore

Where to Celebrate Oktoberfest 2017 in Baltimore

Oktoberfest celebrations are beginning already. Nearly two months of beer swilling and sausage eating? We're in. Prost!...read more ›

by Jennifer Waldera Sep 12, 2017
A Washington Distillery Makes Pickle Vodka and We're Into It

A Washington Distillery Makes Pickle Vodka and We're Into It

Blue Spirits Distilling has created a 120-proof, pickle flavored vodka that is just begging to be poured into your next Bloody Mary....read more ›

by Jessie Donofrio Sep 12, 2017
You Can Now Drink Red Wine Out of a Forty, Just in Time for Fall

You Can Now Drink Red Wine Out of a Forty, Just in Time for Fall

If you're mourning the end of rose-in-a-forty season, don't worry: Forty Ounce Wines is now producing its first red wine in a forty, just in time for ...read more ›

by The Drink Nation Sep 11, 2017
The Elephant is Unveiling a Second-Floor Speakeasy

The Elephant is Unveiling a Second-Floor Speakeasy

Mt. Vernon's The Elephant is opening a gorgeous new upstairs speakeasy concept....read more ›

by Jennifer Waldera Sep 6, 2017
Lagunitas Brewing Co. Has Launched a Cannabis Beer

Lagunitas Brewing Co. Has Launched a Cannabis Beer

Working with CannaCraft Inc., a cannabis-extract manufacturing facility in nearby Santa Rosa, Lagunitas created the SuperCritical Ale, flavored with t...read more ›

by Alexander Frane Sep 6, 2017
Carnival Cruise Lines has Opened the First Brewery at Sea

Carnival Cruise Lines has Opened the First Brewery at Sea

The Miami-based Carnival Cruise Lines has hopped aboard the microbrewing trend with the founding of RedFrog Brewery, the first ever craft brewery on a...read more ›

by Jessie Donofrio Sep 6, 2017
Things No One Asked For: The Guzzle Buddy Beer Bottle Glass

Things No One Asked For: The Guzzle Buddy Beer Bottle Glass

One company is making glasses you can screw right into the top of your beer bottle....read more ›

by Ryan Hudak Sep 6, 2017
SPONSORED
View all Articles

Sign up to get weekly drinking news, bar reviews, events and more sent directly to your inbox!

Close