Main Street, Annapolis

Main Street, Annapolis (must see)

Located between Church Circle and City Dock, Main Street can’t be missed with its ever-busy sidewalks, views of the Annapolis Harbor, and bustling shops. They say that Main Street is the lifeblood of Annapolis and, indeed, represents the very best of what the state of Maryland has to offer. Defined by as much as three centuries of history and lovingly-preserved 18th- and 19th-century buildings lining its five blocks, this thoroughfare is something of a living museum, providing visitors and residents alike with some truly historical experience.

Given the assembly of architectural details, attractive qualities, interesting discoveries, and everyday pleasures found here, it is easy to see why Main Street is a source of pride not only for Annapolitans, but for Americans across the country. Nightlife, dining, and art, as well as shopping take the center stage here, making Main Street a great point to start a day on the town, be it for a leisurely outing, special event, or some other occasion.

There's a contagious energy in the air of Main Street that some call addictive. Just look in any direction and you will surely find something to pique your imagination - physically and visually associated with history, maritime culture, and architectural character. Among the eye catchers are, undoubtedly, the Chesapeake Bay, midshipmen in dress whites, historic landmarks, bars, restaurants and art galleries of every size and description, offering visitors plenty of options to choose from, no matter what they look for. There are also a handful of cafes, ice cream parlors, bookstores, and shops selling souvenirs, jewelry, comics, and apparel aimed at tourists to be found.

Throughout the year, the city and merchants decorate the street with hanging flower baskets, flags, and banners. Each October brings visitors in their thousands who arrive for the world's largest in-water power and sail boat shows taking place at City Dock. The street has a festive atmosphere during the holiday season too, when the Downtown Business Association and businesses along Main Street sponsor Midnight Madness two nights before Christmas to attract holiday shoppers to their decorated stores.

Want to visit this sight? Check out these Self-Guided Walking Tours in Annapolis. Alternatively, you can download the mobile app "GPSmyCity: Walks in 1K+ Cities" from iTunes App Store or Google Play. The app turns your mobile device to a personal tour guide and it works offline, so no data plan is needed when traveling abroad.

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Main Street on Map

Sight Name: Main Street
Sight Location: Annapolis, USA (See walking tours in Annapolis)
Sight Type: Attraction/Landmark
Guide(s) Containing This Sight:

Walking Tours in Annapolis, Maryland

Create Your Own Walk in Annapolis

Create Your Own Walk in Annapolis

Creating your own self-guided walk in Annapolis is easy and fun. Choose the city attractions that you want to see and a walk route map will be created just for you. You can even set your hotel as the start point of the walk.
Naval Academy Campus Walking Tour

Naval Academy Campus Walking Tour

Established in 1845 under George Bancroft, the US Naval Academy is Annapolis' most prominent complex, situated right at the confluence of Severn River and Chesapeake Bay. The Academy's campus has on its territory some of the most beautiful structures in the city. Follow this self-guided walk to explore a variety of attractions, including the museum, outstanding buildings, monuments, the...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 1.7 Km or 1.1 Miles
Annapolis Historical Houses Tour

Annapolis Historical Houses Tour

Having served as the capital of both the Colony/Province and the State of Maryland, Annapolis is rich in history, predating the Revolutionary War by decades, and is one of the first planned cities in colonial America. Although many structures from that era are either gone, destroyed by neglect, or completely renovated, several magnificent 18th century homes are still in place and retain their...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 1.6 Km or 1 Miles
Annapolis Introduction Walking Tour

Annapolis Introduction Walking Tour

Located on the banks of the Severn River, which flows into the Chesapeake Bay, Maryland’s state capital Annapolis, also dubbed “America’s Sailing Capital”, thrives on its nautical roots and colonial history. The town has more 18th century buildings still in use than any other U.S. city. Annapolis is also home to multiple cultural and historic sites, such as the fabulous Kunta Kinte-Alex...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 2.2 Km or 1.4 Miles
Best Pubs and Taverns in Annapolis

Best Pubs and Taverns in Annapolis

As Annapolis is the sailing capital of Maryland, the city enjoys numerous exciting places offering great beer and seafood till late at night. There are pubs, saloons and bars, the majority of them hosting live music nights, as well as different contests. This self guided tour introduces you to the best bars and pubs in Annapolis.

Tour Duration: 1 Hour(s)
Travel Distance: 1.2 Km or 0.7 Miles