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Winter in Annapolis, Plan Your Holiday Escape

Winter in Annapolis brings a mystical charm to our historic, brick-laden streets. Consistently ranked as a Top Christmas destination year after year by Travel + Leisure, and with the Best Holiday Lights Display in Maryland at Lights on the Bay at Sandy Point State Park, Annapolis is the perfect…

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Things to Do, November 2022

Experience the quirky and prideful Eastport vs. Annapolis Tug of War, shop at the largest discount shopping destination in the state of Maryland at Arundel Mills, run the Chesapeake Bay Bridge in our county's Bay Bride Run, or plan a weekend in Annapolis for the Veteran's Day Classic Basketball…

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Holiday Magic

With juuust enough flux still lingering from last year, it’s now critical to flex the steadfast muscle memory of Holiday traditions; and Annapolis has a boatload of them. Fire up the turn table, it’s time to spin the Christmas classics. Yews Light up My Life For 45 years the Annapolis Jaycees…

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Chocoholics Rejoice!

Here’s something sweet to celebrate: the return of the Annapolis Chocolate Binge Festival. Created by the Inner West Street Association (the same team behind the popular First Sunday Arts Festival), the Chocolate Binge Festival takes over the first block of West Street on December 5, in a…

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Fall Haul: Downtown Annapolis Main Street Edition

In November, we celebrate veterans, spending time with family, and of course, Small Business Saturday (November 27)! We visited some of Downtown Annapolis’ hippest boutiques to find out what’s hot for fall…and beyond. Fall Fashion On our jaunt along Main Street, we had to start at Hobo’s flagship…

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First Sunday Arts Festival

First Sundays on West Street If you are looking for the perfect way to spend an afternoon, look no further than the First Sunday Arts Festival in downtown Annapolis. This Sunday will be the last festival of the season, wrapping up the festival’s 20 th year! The festival takes place on the first…

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