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:
 
Stay Warm in Baltimore This Winter With These Hot & Spiced Cocktails

Stay Warm in Baltimore This Winter With These Hot & Spiced Cocktails

There a few spots in Baltimore heating things up with spiced or heated cocktails that warm you from the inside...read more ›

by Jennifer Waldera Nov 27, 2018
Red Spot Whiskey Has Returned after 50 Years Out of Production

Red Spot Whiskey Has Returned after 50 Years Out of Production

After 50 years out of production, Red Spot Whiskey has returned to join the Spot Whiskeys family once again....read more ›

by The Drink Nation Nov 26, 2018
Miller High Life is Now Available in Champagne Bottles

Miller High Life is Now Available in Champagne Bottles

Miller High Life, commonly known as the 'Champagne of Beers,' is now available in actual champagne bottles for a limited run during the holiday season...read more ›

by The Drink Nation Nov 13, 2018
SPONSORED
Visit Drink Baltimore on Your Phone
Jack Daniels is Making a Whiskey Advent Calendar For the Holiday Season

Jack Daniels is Making a Whiskey Advent Calendar For the Holiday Season

Jack Daniels has debuted a boozy advent calendar filled with, naturally, whiskey, just in time for the holiday...read more ›

by The Drink Nation Nov 13, 2018
Behind the Bar: Jason Wise, Director of the SOMM Documentary Film Series

Behind the Bar: Jason Wise, Director of the SOMM Documentary Film Series

For this installment of Behind the Bar, we spoke to Jason Wise, documentary filmmaker and director of the new ...read more ›

by The Drink Nation Oct 31, 2018
Where to Drink Near Patterson Park in Baltimore

Where to Drink Near Patterson Park in Baltimore

What better way to wrap up a run, tennis match, or a walk with the pooch than at a nearby watering hole?...read more ›

by Jennifer Waldera Oct 30, 2018
Beam Suntory Has Launched a Japanese Vodka & Gin

Beam Suntory Has Launched a Japanese Vodka & Gin

Beam Suntory, one of the largest producers of both American and Japanese whiskeys in the world, has introduced two new clear spirits to its lineup: Ha...read more ›

by The Drink Nation Oct 29, 2018
You Can Now Minor in Bourbon at This Kentucky University

You Can Now Minor in Bourbon at This Kentucky University

Thanks to the booming bourbon tourism industry in Kentucky, the state's Midway University now offers a minor in Bourbon Studies as part of their under...read more ›

by The Drink Nation Oct 29, 2018
You Can Make Your Own Whiskey at This Virginia Beach Hotel

You Can Make Your Own Whiskey at This Virginia Beach Hotel

If you've always wanted to make your own whiskey, you're in luck - a hotel in Virginia Beach is letting guests make their own barrels of whiskey....read more ›

by The Drink Nation Oct 15, 2018
Bono Has Purchased a Stake in a New Irish Whiskey Distillery

Bono Has Purchased a Stake in a New Irish Whiskey Distillery

Lots of celebrities have been partnering with distilleries lately, and now, U2's Bono is the latest star to form a partnership with a liquor company....read more ›

by The Drink Nation Oct 15, 2018
SPONSORED
View all Articles

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

Close