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.
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.
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.
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.
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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