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
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