During your stay at Flag House Inn, you’ll have the opportunity to experience dozens of tourist attractions, restaurants, art galleries and antique shops, museums, historic homes & churches, live theater, boat tours/sailing, the Naval Academy, Maryland State House, St. John’s College, walking tours, pub crawls, ghost tours… all the sights and sounds of America’s sailing capital!

And, fun in Annapolis isn’t limited to just the weekend, there is much going on every day in Annapolis. We can always advise on what’s going on as events arise. Here’s a sample:

Here is a great site that lists everything going on around town

Sunday – First Sunday Arts Festival (blog) and concerts at City Dock. Also (June to Sep) – Sunday night movies at Reynolds Tavern 

Monday – Best day of the week for Happy Hour, many ½ price deals.  

Tuesday – Weeknights have the biggest acts at Rams Head on Stage. Check the calendar and book ahead! In the summer, Reynolds Tavern has Shakespeare on the outdoor patio

Wednesday – All year – Irish Music Night (live music) at Galway Bay .Race Night on the Woodwind yacht (June- Sep – also it’s sailing night for all yacht clubs in the summer) & Dinner Under the Stars on West St (June-Sep). Buy a ticket on the Woodwind and we’ll give you a voucher for a free drink .

Thursday – Free concerts at the Maritime Museum in Eastport. (June-Sep)