Annapolis On The Cheap: A Happy Hour Adventure in Naptown

Annapolis on The Cheap


I love the Annapolis beer scene. Yes, there is room for improvement, but there are some great places to catch up with friends and enjoy a pint. Unfortunately, my wallet doesn’t enjoy Annapolis as much as I do. Between Casey and I a couple of beers and food for the two of us can quickly add up to $60 or more. But this doesn’t have to be!

Annapolis has some great happy hour specials for both food and beer. Most places run the same happy hour special all week long, and some others will have an extra special happy hour one day a week. Our plan is to figure out when and where to get the best deals on craft beer and food throughout Annapolis. We’re going to eat and drink our way across this great town so that you don’t have to! Aren’t we generous?

So here is our goal. Two beers each, enough food that we don’t leave hungry, and keep the bill under $30. We’re going to cheat a little bit and not include tip in that $30 limit. Can we do it? Just about every bar in town has a $5 burger night, but that would be too easy, and I can’t bring myself to eat a burger five days a week. We’re also going to judge our success on the quality of the craft beer and food available within our price limit.

You can see where we’ve been so far by clicking here. I even created an Annapolis Happy Hour Calendar to help us figure out when and where to go (I recommend agenda view). You can also sync this calendar on your phone via XML (Android), or iCal (iPhone) if you want to use it yourself. Just keep in mind that happy hours sometimes change. The calendar will change with them, so let me know if you spot a new happy hour in town.


Do you know a place around Annapolis where we should attempt our $30 happy hour challenge? Spot a change in one of the listed happy hours? Head over to The Beer Spy Facebook page (or comment here) and let me know!


  1. Excellent! Thank you. We live in Annapolis – it is hard to find all of this information in the same place.


  2. Is this calendar still up to date??
    Also, if you haven’t added it yet you should check out the Annapolis Smokehouse for this happy hour project 🙂


  3. The bar at O’Callahan hotel West St DT Annapolis has great domestic draft prices ($2.50 pint). Great food deals depending on day of the week. 4:00-7:00 pm M-F & sometimes on wkends


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