Annapolis has a vibe. Certain cities do. Songs are written about New York City’s vibe. San Francisco too. No songs about Annapolis; it’s not that big, but it is historic, lively and fun.

6 Reasons to Visit Annapolis

Not a History Snooze

Here’s where the vibe comes in. Annapolis is the confluence of history, commerce, political power and boating.
Main Street in Annapolis going downhill to the harbor.
Main Street in Annapolis going downhill to the harbor. This is the main shopping section, but there are many shops off on the side street.
The constant tug of priorities means the town hung onto it colonial buildings but was prevented from turning the historic area into a giant museum. The boating community actively keeps the town from becoming stuffy or pretentious.
Power boat heading into Ego Alley for a pivot
When you visit Annapolis, you’re strolling around and through history on the way to find a good crab cake and a beer. The entire downtown was the country’s first National Historic Landmark, created in 1966.


Annapolis was the commercial powerhouse of the Chesapeake Bay, essentially putting other commercial centers around Bay out of business. That fizzled when ships got too big for Annapolis’ little harbor and started docking in Baltimore.
Historic Annapolis map of City Dock
Historic Annapolis map of City Dock (Courtesy Maryland State Archives)
Annapolis' inner harbor now, called Ego Alley or City Dock
Annapolis’ inner harbor now, called Ego Alley or City Dock
The British came through Annapolis when they tried to retake the colonies in the War of 1812. Slave ships unloaded in Annapolis for generations before the Civil War.


While its commercial vigor fizzled a bit, Annapolis is still a political powerhouse. The Continental Congress met in Annapolis to ratify the “Treaty of Paris,” formalizing separation from Great Britain.
Maryland State House, Annapolis
The Maryland State House served briefly as the nation’s capitol and has been the Maryland state capitol ever since the official end of the Revolutionary War in 1784.
The Maryland State House continues as the longest continuous-use state capitol in the U.S.

More Original 18th Century Buildings Than Any Other U.S. City

Five of the Colonial Georgian mansions in Annapolis are open to the public. Others are still used for homes or have been turned into offices, shops or restaurants. James Brice House, Annapolis, MD Walk any direction from the business district and you’ll find beautifully maintained Victorians and 19th Century mansions, as well as colonial watermen cottages.

“Sailing Capital of the World”

Actually, Annapolis competes with Newport, Rhode Island, for the title. Newport has hosted America’s Cup regattas, while Annapolis leads in number of boats compared to the population.


But the Annapolis city council settled the issue by passing a proclamation in 1995. So, there you go Newport. Wednesday sailboat races in Annapolis


Historic Higher Learning

Downtown Annapolis is the home of the U.S. Naval Academy and St. John’s College, a 300-year-old liberal arts college unlike no other in the country.


 St. John’s was created before colleges had curriculums and it hasn’t changed. Students study the “great books” toward a liberal arts degree. St. John's College campus in Annapolis St. John’s College campus in Annapolis The two institutes of higher learning compete throughout the year, with the most popular event being the annual Croquet Match in the spring where everyone dresses up Great Gatsby-style to watch cut-throat croquet. No joke.


The result is a vibrant nightlife. Nearly every bar — and there are a lot of them — have music every weekend. Walking about you’ll find casual hipsters, formally-dressed midshipmen and mid-life boaters in their athletic wear.

Shops & Eateries

The historic downtown is full of unique boutiques and restaurants. Internationally renowned Hobo bags started here and still has their original shop downtown. ain Street in Annapolis, Md Across Spa Creek, a ten minute walk from the harbor, there’s Eastport, home to a boating community and, more importantly, lots of boaters’ bars. You’ll also come across some great water views. Spa Creek Bridge in Annapolis, MD Bridge to Eastport across Spa Creek. This is the view from the Eastport side facing downtown Annapolis. Eastport residents march into City Hall each year to announce the ‘hood is succeeding from Annapolis. They settle the issue with a tug-of-war across the “creek”.
Eastport Tug of War in Annapolis
The annual “Slaughter Across the Water” tug-of-war between Annapolis and the Maritime Republic of Eastport. The rope goes across the water.
Eastport is where you’ll find a high-end “restaurant row” of fish and steak houses with views of Annapolis harbor.


While Main Street in historic downtown is home to an unusual number of colonial bars.
1747 Pub at Reynolds Tavern, Annapolis
1747 Pub in the basement of Reynolds Tavern. This is the former kitchen of the historic colonial home. Live music is tucked into the corner on weekends. (photo courtesy Reynolds Tavern)

The main places to see are City Dock (the waterfront), Main Street (the business/shopping district), State Circle (state capitol area), U.S. Naval Academy, Eastport (historic neighborhood of former watermen homes & boaters’ bars), and West Street (uptown area of bars & restaurants).

Cool Tours Abound

The Visitor’s Center (26 West Street) is a good place to start. It has public restrooms and people standing by to answer questions. You’ll find ghost tours, home tours, food tours and even a scavenger hunt tour. Here’s a list of walking, boating, Segway, cycling, kayaking tours.
Annapolis tour guide in Colonial costume
An Annapolis tour guide in Colonial costume
They have a map for a self-guided Historic Walking Tour. There’s also a free walking tour app for your smart-phone or tablet. The Visitor’s Center has contact information for guided tours by private companies.
Annapolis Visitor Center
The Visitor Center’s location is a great starting point, while our helpful volunteers are a great resource for things to do, events happening in the area, suggestions, and much more.
The times of the tours change depending on the season, so go online or call first if you’re on a tight schedule.

Click for More…

What’s on Main Street?

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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