One of the oldest cities in the United States, Annapolis was once known as the “Athens of America.” Much like its larger neighbors, Baltimore and Washington, DC, this Maryland city brims with history and culture, and makes for an exciting getaway that appeals to all kinds of travelers.
Located on Chesapeake Bay, Annapolis is also known as “America’s Sailing Capital,” and thus the perfect destination for water-lovers. Here, you can enjoy kayaking, fishing, boating and windsurfing when the weather is nice. In the summer, watch the city’s annual sailboat races, hosted every Wednesday night. Those who would rather keep dry can dine at the cozy pubs and restaurants that line the waterfront, or shop at local boutiques.
Annapolis is also home to a number of beautiful parks, must-see museums, and a vibrant arts district. Check out some of the city’s stunning historic buildings and peruse the art galleries. However, you chose to travel, our inclusive Annapolis guide is for you.
1. Explore the Annapolis Historic District
It is no surprise that the Annapolis Historic District is a recognized National Historic Landmark District. Clad in red bricks and Colonial Style Architecture, this charming district is densely packed with historic sites and structures dating back to the 18th century. Some of the district’s most famous sites include the U.S. Naval Academy, the Maryland State House and St. Anne’s Church, the first church built in Annapolis.
The historic district is extremely walkable, and there are plenty of walking tours, such as this one by Watermark, to help you dive into this city’s rich history. If you’d rather explore the area independently, take this self-guided walking tour.
2. Tour the Maryland State House
The Maryland State House is a must-see if you’re touring the historic district. This building dates back to 1772, but its legislative use continues today, making it the oldest state building that is still in use. This building also briefly served as the nation’s capitol, and it is a designated National Historic Landmark.
This historic building saw witness to several important historical events. This is where George Washington resigned as commander in chief of the Continental Army and where the Continental Congress ratified the Treaty of Paris, marking the end of the Revolutionary War. Learn about these historical moments and many more while exploring a range of exhibits and enjoying the building’s architecture. The state house is open to the public every day from 8:30 a.m. – 5:00 p.m.
3. See the Banneker-Douglass Museum
The Banneker-Douglass Museum is Maryland’s official African American heritage museum. Located within the former Mount Moriah African Methodist Episcopal (AME) Church, the museum preserves and promotes the state’s African American history. It is named after Black leaders Benjamin Banneker and Frederick Douglass, both of whom were Maryland residents. The museum also highlights a number of other Black Marylanders, including Kunta Kinte, Harriet Tubman and Thurgood Marshall. It is open from 10 a.m. until 4 p.m. Tuesday through Saturday, and admission is free.
4. Travel back in time in the William Paca House
Travel back in time and visit the William Paca House & Garden, a five-part brick mansion surrounded by a stunning 2-acre garden. A designated National Historic Landmark, the house was built by Founding Father William Paca, who signed the Declaration of Independence and served as Maryland’s third Governor.
The Georgian mansion has been restored to its 18th century appearance, and now provides an insight into how upper-class families lived in colonial Annapolis. Admission for a self-guided tour is $5 and for a guided tour is $12. The House’s hours are listed here.
5. Tour the U.S. Naval Academy
Taking a tour of the United States Naval Academy is one of the most popular Annapolis attractions. Here, you’ll get a first-hand glimpse at the life of a midshipman while exploring the history of the U.S. Navy.
Take the 90-minute historical walking tour through the campus and see historic sights including the Tripoli Monument, the Herndon Monument, the Main Chapel, and the crypt of naval hero John Paul Jones. Tickets are $12 and all proceeds go to the Brigade of Midshipmen.
While you’re there, be sure to check out the U.S. Naval Academy Museum. More than 100,000 people visit this public maritime museum every year to learn about the history of the U.S. Navy, and all those who served at sea. The museum also boasts the largest ship model collection in the world. Exhibits span two floors, and the museum is engaging for both kids and adults. Museum hours are listed here and admission is free.
6. Cruise the Chesapeake Bay
A trip to “America’s Sailing Capital” would be incomplete without, well, sailing. Hop aboard one of the city’s tour boats and cruise the Chesapeake Bay.
One such cruise, the 74-foot Schooner Woodwind, offers 2-hour public tours with views of the Severn River, the US Naval Academy, the Annapolis skyline and possibly the Chesapeake Bay Bridge, depending on the weather. The sailing season will reopen in April 2023. Ticket rates range between $71.95 and $75.25 per person, depending on the day of the week.
Other tour boats include the Watermark Journey public cruises, with tours ranging between 40 minutes and three hours. Chesapeake Windsail Cruises also offers daily excursions as well as private and theme cruises aboard the Eternal Hope, a 42-foot sailing yacht.
7. Shop on Main Street
Stroll down Main Street and enjoy the city’s charming maritime culture, 18th century architecture and relaxing shopping ambience. This five-block long strip is packed with restaurants, bars, art galleries, and more than 90 bustling shops selling everything from books to spices to pottery.
8. Relax at Quiet Waters Park
For a relaxing natural getaway, spend the afternoon in Quiet Waters Park, located between the South River and Harness Creek. Spend the afternoon hiking, biking or jogging in 340 acres of park land. Or bring snacks and have a picnic by the water. The park is pet friendly, and includes a dog park and a dog beach. Kids will enjoy the playgrounds scattered across the park, and adults will enjoy the local art displayed in the Visitor Center’s two art galleries. A day pass costs $6 and the park is open between 7 a.m. and sunset.
9. See the Kunta Kinte-Alex Haley Memorial
Located in downtown Annapolis, the Kunta Kinte-Alex Haley Memorial is inspired by the Pulitzer Prize-winning novel Roots by Alex Haley and depicts the character Kunta Kinte, an African slave who is based on the author’s ancestor. The memorial represents the place where Kunta Kinte arrived in the United States, and it remains the only U.S. memorial that commemorates the name and the arrival place of an enslaved African.
The memorial is made up of several sculptures, the most prominent of which depicts Alex Haley reading a book to three children of different races. These sculptures represent Haley’s vision for national racial reconciliation while stressing the importance of family history. Over 1,000,000 people visit the memorial every year.
10. Visit Ego Alley
Despite its misleading name, Ego Alley is not an alley. Instead, it is a short, narrow waterway in the City Dock area. This canal is often inundated with expensive yachts parading through the waterway, thus the name “ego alley.” Spend an afternoon watching boats and relaxing along the canal. If you’re hungry, stop in at Storm Bros. Ice Cream Factory or at one of the waterfront restaurants.
11. Relax at Sandy Point State Park
Take a break from museum-hopping and spend an afternoon relaxing at Sandy Point State Park. Located on the shores of Chesapeake Bay, this 786-acre state park includes a mile-long swimming beach, serviced by lifeguards in the summer months.
Boasting beautiful waterfront views, the park offers opportunities for biking, hiking, swimming, fishing and bird-watching. There is a concession stand as well as a number of picnic tables and playgrounds. With more than 20 public boat ramps, the park is also an ideal spot for those traveling via boat. Entrance to the park is $5 per person on weekdays and $4 on weekends.
12. See the Hammond-Harwood House
This National Historic Landmark was built in 1774 by architect William Buckland. The colonial home has been operating as a museum since 1940, and provides a window into the lives of those that once occupied it.
Book a 30-minute or 60-minute tour or take a self-guided tour to learn more about the building’s architecture and about the families and enslaved people who lived there. View the home’s collection of fine art and explore the carefully-maintained gardens surrounding the home.
13. Visit the Annapolis Maritime Museum
Located in what was once the last oyster-packing plant in Annapolis, the Annapolis Maritime Museum harbors a range of exhibits that preserve and promote the city’s maritime history. The museum explores the ecology of Chesapeake Bay and demonstrates the role that oyster-packing had on the local economy.
The museum also features aquariums, a maritime-themed art gallery, a holographic waterman and a four-person digital game. The museum is open from 10 a.m. to 3 p.m. Tuesday through Sunday. Tickets are $7 for adults and $5 for kids.
14. Shop at the Pennsylvania Dutch Farmer’s Market
Shop for fresh produce, cheeses, candy, baked goods and more at the Pennsylvania Dutch Farmer’s Market. Most of these products are made in Lancaster, Pennsylvania by Amish farmers, which is why the market is sometimes referred to as the “Amish market.” Located in the Annapolis Harbour Center, this indoor market is open Thursdays through Saturdays.
15. See the Maryland World War II Memorial
Overlooking the Severn River, this open-air memorial pays tribute to 6,454 Marylanders who died during WWII. Their names are inscribed onto rectangular stone columns, arranged in a large amphitheater. Dedicated in 1998, the memorial serves to recognize those who lost their lives defending their country.
16. Visit Historic London Town and Gardens
Okay so this one isn’t technically in Annapolis, but just eight miles away, the Historic London Town and Gardens is a must-see if you’re a history buff. This 23-acre museum includes a historic house from 1760 and several reconstructed colonial buildings that mimic those that may have made up London Town, a seaport settlement founded in 1683. The buildings are also surrounded by stunning gardens, including an eight-acre Woodland Garden and a Sound and Sensory Garden. Tickets are $10 for adults and $3 for kids and the museum is open from 10 a.m. until 4 p.m. Wednesdays through Sundays.
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