Sightseeing in Annapolis, MD

As the nation’s oldest state capital, Annapolis is dripping with historical charm and fascinating sights. Founded by Puritans in 1649 along the banks of the Severn River and Chesapeake Bay, the city played a pivotal role during the Revolutionary War, serving as the first national capital from 1783-1784. It is famous for its colonial-era buildings, romantic cobblestone streets, and charming harbor district with shops, restaurants, and family-friendly attractions. Learn all about Annapolis sightseeing down below!

Historic Downtown Annapolis Sightseeing

The heart of Annapolis dates to the late 18th century and is an excellent place to explore, either on a self-guided tour (visit here for an example) or as part of historically themed tour such as those offered by Watermark. While you stroll its charming streets, you will be treated to historic Annapolis sights such as romantic brick townhomes, idyllic streets, and fantastic examples of Beaux-Arts architecture, including the waterfront manicured grounds of the U.S. Naval Academy. You can visit the country’s oldest capital building, the Maryland State House (built in 1772). Marvel at the building’s large wooden dome (the largest in the country), and the fact it was made WITHOUT nails. The nearby St. Anne’s Church is home to a historic cemetery and stunning Tiffany glass windows.

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Outdoor Annapolis Sights

Annapolis is home to many resplendent mansions, many with world-class gardens and wilderness areas, which make for great Annapolis sightseeing spots. The grounds of the William Paca House – a national historic landmark – include a 2-acre walled garden, walking paths, and lush vegetation that perfectly complements the Georgian mansion. While it doesn’t have the same immaculate grounds, the Hammond-Harwood House is equally historic, equally famous, and equally charming. Designed by William Buckland in 1774, it boasts an impressive collection of colonial furniture.

If you require something more active, there are numerous parks throughout the greater Annapolis area with over 87 miles of walking trails, many along the water’s edge. Quiet Waters Park is quite popular with its cherry blossoms during the spring, extensive walking trails and gardens, and a playground for the kids.

Down by the Docks

Downtown Annapolis is also home to the City Docks, the former heart of this colonial city. Here, the streets are lined with cozy cafes, boutiques, gift shops, art galleries, and more. There is a host of friendly neighborhood pubs and delicious restaurants, including some of the finest dining in the city. Nearly everywhere you go has splendid views of the river, harbor, and the bay, making it a perfect place to grab a meal any time of year, but especially during the weekend sailboat races in May and the annual boat show in October. We always hear good things about the crab cakes!

Annapolis has plenty of family activities to offer as well, including an aquarium, several museums, activity centers offering laser tag and go-karts, and even pirate-themed harbor cruises. No matter what sort of adventure you seek, Annapolis has something for everyone and At Home Annapolis has the perfect vacation rental to match. Browse our site to pick out your home away from home today and go sightseeing in Annapolis, MD! If you’re visiting Annapolis during Commissioning Week, view our best Commissioning Week weekly rentals, condos, or lodging rentals!

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