12 Best Things to Do in Annapolis, Maryland

Educate Yourself at the Kunta Kinte-Alex Haley Memorial

Commemorating the spot where Kunta Kinte and countless other enslaved Africans first arrived on U.S. soil, the Kunta Kinte-Alex Haley Memorial is definitely worth visiting on your next trip to Annapolis.

Inspired by the true story behind Alex Haley's masterpiece, "Roots: The Saga of an American Family," the memorial features a series of plaques offering messages of hope in light of the devastating legacy of slavery in the U.S., and a life-size sculpture of Alex Haley sharing his story with children of all ethnic backgrounds. There's also a compass rose, designed to inspire you to discover your own family history, and a replacement plaque — the original was stolen shortly after it was put on display in 1981 — marking the place where Kunta Kinte and so many others began their lives in bondage in this country.

Chill Out in Quiet Waters Park

After a long day of sightseeing, head about 20 minutes south of Annapolis to Quiet Waters Park for a chance to chill out in nature for a while. With 340 acres, a number of hiking trails, playgrounds, and picnic spots, there's plenty of room to spread out and take a breather.

Check the website to see if any concerts will be happening when you're in town, as the U.S. Naval Academy Blues and Gold band, Annapolis Symphony Orchestra, and several local blues, funk, country, rock, and jazz bands have been known to perform on summer evenings as part of the city's Concerts in the Parks series.

Tour the United States Naval Academy and Catch a Game

Home of the 4,000-strong brigade of midshipmen, the United States Naval Academy in Annapolis is the training ground for officers of the U.S. Navy and Marine Corps. It's also where you'll find the Naval Academy Museum, which features more than 50,000 artifacts and is home to the famous Gallery of Ships.

Just a block away from the Annapolis City Dock, the main entrance to the U.S. Naval Academy is located at Randall and Prince George Streets. Guided tours of the Academy and museum depart from the Armel-Leftwich Visitor Center, showing visitors the renovated chapel and its massive pipe organ, the Lejeune Physical Education Center and its Athletic Hall of Fame, Dahlgren Hall and its Drydock Restaurant, and Bancroft Hall, a dormitory that houses more than 4,400 midshipmen in over 1,700 rooms, among other points of interest.

About a mile and a half away, year-round events bring the community of Annapolis together at the state-of-the-art sports facility known at Navy-Marine Corps Memorial Stadium. Serving as the home field of the Navy Midshipmen football team, the men's lacrosse team, and the Chesapeake Bayhawks lacrosse team, the Navy-Marine Corps Stadium also hosts a wide range of festivals and events such as the Annapolis 10 Miler, Annapolis Rotary Crab Feast, and the Annapolis Arts & Crafts Festival.

Learn About Black History at the Banneker-Douglass Museum

Dedicated to two of the most influential figures in the history of abolition in the United States, Benjamin Banneker and Frederick Douglass, the Banneker-Douglass Museum is an incredible African American heritage museum in Maryland.

While the museum offers guided tours through the permanent and temporary displays, guests can also freely browse the galleries on their own. Admission to the museum is free (tours cost $25 for 30 participants), though donations are highly encouraged to help maintain the exhibits.

Catch a Blue Angels' Airshow

If you're visiting Annapolis in May, you can also catch a special Blue Angels Airshow in the skies over the U.S. Naval Academy during the annual USNA Commissioning Week. The two-day air show takes place during the first two days, while the graduation flyover at the Navy-Marine Corps Memorial Stadium takes place on the last day.

During the air shows, the famed Blue Angels, a team of 16 top Navy and Marine jet pilots who tour the country every spring and summer, lead the newest graduates in a series of performances. Visitors can watch the show from either Navy-Marine Corps Memorial Stadium or along the banks of the Severn River on the U.S. Naval Academy campus.

Go Sailing or Powerboating

Annapolis is America’s sailing capital and the adjacent Chesapeake Bay is a great destination for all sorts of fun out on the water. Fortunately, a number of public cruises, boat tours, and private charters are available to take you out on the water, providing a great way to see some of the best scenery in the region. A variety of sailboats and powerboats are available for private and public charters, and guests may take a short one or two-hour cruise, a half- or full-day cruise, or a multi-day excursion aboard a cruise line.

Schooner Woodwind Sailing Cruises departs from the Annapolis Waterfront Hotel multiple times a day for two-hour excursions into the bay. Meanwhile, Note that the Liberte is only available for cruises in the spring and fall. If you're traveling for children, try Pirate Adventures on the Chesapeake, which invites younger guests to sail aboard the Sea Gypsy for their special occasion.

Take a Guided Tour of the City

If you'd rather stay on dry land during your trip to Annapolis but still want to take in all the sights, try taking a guided tour through the city to learn about its history. Explore from an electric eCruiser or take in the sites, architecture, and panoramic water views on a walking tour instead.

Annapolis Tours offers a variety of adventures geared toward all sorts of interests. Guided by a local expert—oftentimes dressed in period garb—guests can learn about Annapolis' many points of interest, including the oldest continually running state house in the United States, the U.S. Naval Academy, and the lesser known St. John's College.

Downtown Annapolis and its historic district are both extremely bike friendly—for a real treat, rent a bike from Annapolis Velo and take on the town at your own pace.

Another fun bike option, the Eco Fun Tour, takes guests on a two hour "environmental and historical experience" over the course of five miles. Led by a lifelong resident of Annapolis, this super-local tour lets visitors in on little secrets of the city the host has uncovered during his life here.

Feast on Steamed Crabs

Restaurants serving Maryland’s famous blue crabs dot the 400 miles of shoreline throughout Anne Arundel County, and local favorites help contribute to the claim that some 3.9 million crabs are cracked here each year.

The Annapolis Rotary Crab Feast, held at Navy-Marine Corps Memorial Stadium the first Friday in August each year, is recognized as the largest crab feast in the world. You can also usually find a variety of crabs at the annual Annapolis Seafood Festival each September.

If you can't make it to Annapolis in August or September for these events, stop by nearby restaurants like Mike’s Crab House (with two locations in Riva and Pasadena), Cantler’s Riverside Inn, or Skipper’s Pier in Deale for delicious seafood dishes all year long.

Tour the Maryland State House

Known as being the oldest continually operating capitol building in the country, the Maryland State House was first used by the Continental Congress in 1783. Today, the Maryland General Assembly convenes at the State House for three months each year—the rest of the time, visitors can tour its historic halls.

The State House is open daily from 8:30 a.m. to 5 p.m. but is closed on Christmas and New Year's Day. To learn about the rich and historic past of the oldest state capitol still in continuous legislative use, self-guided tour information is available. Note that you will have to show photo identification and step through a metal detector to enter the building.

Attend an Event or Festival

While the residents of Annapolis celebrate everything from the holidays to the city's culture and history throughout the year, the summer is certainly the busiest time for outdoor festivals and events. Check the Annapolis tourism website to see what's happening during your trip.

On weekends during the summer, catch the summer concert series, which brings street performers and musicians to the Annapolis waterfront for afternoon and evening performances. Stop by the first Sunday of each month for the First Sunday Arts Festival, where craft vendors, artists, musical acts, and street performers gather to celebrate the arts.

If you're visiting during the fall and winter, you'll find plenty of ways to celebrate the holidays in Annapolis, too. Depending on when you visit, you're likely to encounter a number of great Halloween parties, Thanksgiving parades, Christmas lights and villages, New Year's Eve events, and even Valentine's Day adventures.

Watch the Wednesday Night Sailboat Races

One way you can truly celebrate the sailing culture of Annapolis is by watching a boat race in the Chesapeake Bay starting at the Annapolis Yacht Club. Races begin the final Wednesday in April and run through the second Wednesday in September, and the starting gun for the first race is usually fired around 6 p.m.

During the weekly event, more than 130 sailboats race through shimmering waters around several marks in Chesapeake Bay and return to Spa Creek for a finish in front of the Annapolis Yacht Club. This full service, year-round private yacht club provides a variety of programs for members as well as some special events even non-members can enjoy.

Stop by the Annapolis Yacht Club to learn more about cruising for sailors and power boaters, to enroll in a vigorous junior sailing program, to take part in educational winter activities, or to attend social or first-class dining events.

Visit the Annapolis Maritime Museum

The Annapolis Maritime Museum explores the maritime heritage of the city and the Chesapeake Bay with a variety of exhibits and live entertainment. Learn about the life of seamen and the seafood industry of yesteryear at the Bay Experience Center, housed within the area's last remaining oyster packing plant. Then, board a boat and take a 1.5-mile trip out to the Thomas Point Shoal Lighthouse to tour the last remaining screw-pile lighthouse in its original Chesapeake Bay location.