Annapolis: Main Street

Main Street is the city’s center, the heart of boutique shopping, bars and restaurants in Annapolis. It goes from the City Dock waterfront up the hill to Church Circle

Both sides of the street are lined with shops that stay open late on the weekends and often on the weekdays during the summer and certain holiday seasons.

Some of the boutiques have owners who travel to New York City’s fashion district or overseas to buy the latest styles. But there’s also tourist shops and local artisans.

Annapolis main street
Downtown historic Annapolis from the waterfront, facing uphill toward the State House

You’ll find a few streets that shoot off of Main Street and those also have shops. The original Hobo bags, sold around the world, is still on one of those side streets (194 Green Street) in a renovated 19th Century townhouse just off Main Street near City Dock.

Be aware that art galleries and artisan shops can be tucked on the upper floors or behind of some of the colonial buildings. The entrances can be deceiving.

One of the popular restaurants, Fox’s Den, is a door leading downstairs with a sign that only has a Fox face on it, British-style.

Fox's Den, an American craft gastropub on Main Street in Annapolis.
Fox’s Den, an American craft gastropub on Main Street in Annapolis. The only sign is a fox head hanging over the door to the underground restaurant.

There is an art gallery on Main that’s jam-packed with original art and prints from internationally-known artists. It’s in a small space for large pieces and a big inventory. 

In other words, look carefully if you’re searching for high-quality at a fair price whether it’s art or clothing.

Main Street in Annapolis at night
Main Street in Annapolis, open for business often at night.

It’s been our experience that shop-keepers in Annapolis are generally friendly and like to chat. While they may not bargain down the price a whole lot, they’ll try to set you up with what you’re looking for in your price range.

Also on Main Street you’ll notice several “alleys.” They’re narrow walkways to the next street. Don’t be afraid to explore and walk through them. Locals use these as a short-cut and they’re highly popular walkways.

Chancery Lane in Annapolis
Chancery Lane is one of Annapolis’ pedestrian alleys. It’s a shortcut from Main Street to the state capitol.

Alleys on the side of Main Street opposite the State House leads you to a residential neighborhood of colonial homes. The alleys on State House side also take you to Capitol Circle and West Street, another shopping/bar/restaurant area.

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6 Reasons to Visit Annapolis

City Dock/Ego Alley (downtown waterfront)

State Circle (state capitol area)
West Street (hipster area)
Maryland Avenue (antique row)
Eastport (historic waterman-neighborhood)
Colonial Annapolis
U.S. Naval Academy
Haunted Houses & Pubs
What Else?
Getting Around

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