This Charming Maryland Town Combines Naval Power, Cobblestone Streets, and Steamed Blue Crabs

Annapolis, Maryland

Annapolis is that rare state capital that never lost its soul. The streets still tell stories of revolution and sailing glory, while dock bars and seafood joints keep the maritime spirit alive. Meanwhile, midshipmen march past buildings older than the country itself. Here’s what you need to know about exploring Maryland’s waterfront capital.

Colonial Buildings Line Historic Downtown

This waterfront town still holds 120 buildings from the 1700s. The 300-year-old buildings now hold restaurants, specialty shops, and art galleries.

Governor Francis Nicholson planned the city in 1695 with circles and streets that spread out like wheel spokes, typical of Georgian architecture.

The brick streets connect Church Circle and State Circle with old school cobblestone paths that once felt George Washington’s footsteps.

America’s Oldest Working Capitol

From November 1783 to August 1784, the Maryland State House served as the nation’s first peacetime Capitol, where the Treaty of Paris ended the Revolutionary War.

The dome, North America’s largest wooden one, features a 28-foot lightning rod topped with a copper-covered wooden acorn symbolizing strength.

Local architect Joseph Clark designed the amazing wooden dome in 1772, making it entirely of cypress timber and iron straps.

Georgian Mansions Show Off Brickwork

Many historic homes in Annapolis like the Charles Carroll House and Chase-Lloyd House, show the nation’s largest collection of Georgian architecture.

The Hammond-Harwood House displays excellent brickwork from the 1700s by British artisan John Rawlings.

William Paca finished his home and garden in 1765 before signing the Declaration of Independence and later becoming Maryland’s Governor.

Naval History Lived Here Since 1845

The U.S. Naval Academy out here is the second-oldest military college in the nation, showing off French-styled Second Empire architecture.

The father of the U.S. Navy John Paul Jones, rests in a beautiful domed chapel house inside a fancy tomb.

Deep from the late 1800s, you’ll see the waterfront spot where Fort Severn from the War of 1812 once protected the harbor.

The museum also houses the Beverly R. Robinson Collection (more than 6,000 prints of maritime events) dating from 1514 to World War II.

A Museum For Chesapeake Maritime Traditions

The Annapolis Maritime Museum tells the story of Chesapeake Bay’s boating history from its spot on the riverfront in the Eastport neighborhood.

The newly updated museum fills 2,500 square feet with hands-on exhibits where you can look at historic boats and walk on docks that stretch into Back Creek.

The outdoor space provides great water views while teaching about Annapolis’s deep ties to sailing traditions and the Chesapeake Bay oyster business.

Boating Heritage Surrounds the Marina

In downtown Annapolis, Ego Alley is a narrow waterway where small sailboats and fancy yachts show off, while waterfront restaurants line the marina.

Try authentic sailing aboard the Schooner Woodwind or learn from pros at the Annapolis School of Seamanship, which has taught sailors for over 70 years.

Rent paddleboards, kayaks, and small boats from places like Capital SUP and Annapolis Canoe and Kayak if you prefer exploring on your own.

The city hosts the famous Wednesday Night Races from late April through August when more than 100 yachts gather to compete on the bay.

Shops From 1700s Await on Main Street

Main Street’s cobblestone path slopes toward the harbor, inviting you to eat and shop before heading to State Circle and Maryland Avenue.

Shops sit inside buildings from the 1700s, many keeping original features like exposed brick walls and hand-cut wooden beams.

These stores sell nautical items, fine art, antiques, and handmade goods unique to the Chesapeake region

The Orange Deli Serves Annapolis Staples

Chick & Ruth’s Delly (opened in 1965) has been serving people for over 50 years.

It’s bright orange and yellow walls have witnessed lawmakers, Navy midshipmen, and tourists in close quarters, between neighboring tables.

Order tall sandwiches and famous Maryland crabcakes. Their daily Pledge of Allegiance tradition continues, a practice kept since the deli first opened.

Fresh Blue Crabs Cooked at the Waterfront

Cantler’s, built over the water with quiet Mill Creek views, has served fresh blue crabs, steamed in Old Bay (Maryland spice mixture).

Try McGarvey’s Saloon & Oyster Bar, around since 1975, for regional dishes near City Dock. Don’t forget Sam’s Waterfront Cafe’s locally harvested shellfish.

The 1692 Church Started Annapolis’s Circular Layout

St. Anne’s Church resonates in its peaceful spot on Church Circle.

First established in 1692, the current building represents the third version, featuring beautiful stained glass windows and a traditional pipe organ.

St. Anne’s keeps records dating to the early 1700s and holds traditional Anglican services that have stayed mostly unchanged for centuries.

Walking Trails Wind Through 340-Acres

Quiet Waters Park spreads across 340 acres just minutes from downtown, offering a natural break from city life.

The park features paved paths overlooking Harness Creek and South River. You can explore outdoor sculptures in the gallery.

The grounds include picnic areas, pavilions for groups, and several lookout points that showcase the Chesapeake’s natural scenery.

Harbor Taxis Shuttle Between Historic Sites

Take an Annapolis Water Taxi from the harbor to see Chesapeake Bay, as boat captains share historical facts and maritime tales along the way.

Since 1972, these boats have ferried passengers between Annapolis Harbor, Eastport, and Back Creek, stopping at waterfront restaurants, marinas, and hotels.

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