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If you love history, architectural marvels, vintage theaters, and cozy restaurants, then add the Colonial Annapolis Historic District to your itinerary.
A fun fact is that Annapolis was one of the earliest planned cities in Colonial America. Designed in 1695 by Governor Francis Nicholson, the layout resembled European cities. The Baroque street plan with circles and diagonal streets took advantage of the waterfront's natural landscape.
The district is home to over 120 preserved 18th-century buildings, making it one of the best places to experience colonial architecture. Highlights include the Maryland State House, the oldest state capitol still in use. Here, George Washington resigned as Commander-in-Chief of the Continental Army.
Nearby, St. Anne's Church and the William Paca House and Gardens offer a glimpse into the lives of Annapolis's wealthiest residents during this period.
Annapolis also briefly served as the nation's capital from 1783 to 1784. During this time, the Continental Congress met here and ratified the Treaty of Paris, officially ending the Revolutionary War.
Continue your interest in American military history with a tour of the nearby United States Naval Academy. At the Armel-Leftwich Visitor Center, you can purchase tour tickets, view exhibits, pictures, and films. If you're there for parade days, head to Worden Field to watch the full Brigade of Midshipmen perform at 4:00 PM.
For a taste of the arts, catch a live performance at The Colonial Players theater or peruse the artwork at any of the galleries and museums.
Today, the district's cobblestone streets, historic homes, and bustling waterfront bring history to life, making it a must-visit on yourMaryland getaway.
Colonial Annapolis Historic District: Fun Facts & Cool Features
Whether you're a fan of architecture or not, walking the historic streets will be a head-turning experience! You'll spot Georgian, Federal, and even 19th-century French influences. A prime example is the Hammond-Harwood House, designed by British architect William Buckland. The home is a masterpiece of Georgian design and is currently a museum, showcasing art, tours, and exhibits.
Speaking of historic homes, plan on visiting the homes of three men who signed the Declaration of Independence. These are the Chase-Lloyd House, the Charles Carroll House, and the William Paca House. The latter offers tours of the home, estate, and gardens, making for an immersive history lesson.
The waterfront adds another layer of charm. Known as the sailing capital of the world, Annapolis's harbor has been a hub of activity since the colonial era. Today, it's a lively area filled with shops, restaurants, and events. It's also where you can sign up for a sailing adventure with outfitters like Schooner Woodwind Sailing Cruises.
Museums are as plentiful as the historic homes and buildings! From the U.S. Naval Academy Museum, showcasing military memorabilia, to the Banneker-Douglass-Tubman Museum, honoring African-Americans throughout the ages, there's something for everyone.
After working up an appetite while sightseeing, you're steps away from quality cuisine at hotspots like the Iron Rooster-Annapolis and Osteria 177, both within walking distance and each with a unique menu and ambiance. Also sprinkled throughout the downtown are cafes, clubs, wine bars, and cocktail lounges.
With so much to see and do at the Colonial Annapolis Historic District, chances are you'll visit more than once on your Maryland vacation!
Local Tips
- Wear comfortable shoes for walking on cobblestone streets.
- Bring a valid U.S.-issued ID or passport to visit the Naval Academy.
- Stroll down Main Street for unique shops and great local dining.
- Visit early in the day to avoid crowds and enjoy cooler weather.
- Parking can be tricky; consider public transportation or ride-sharing.



