10 Best Things to Do in Annapolis, Maryland

Annapolis, Maryland, the historic seaport situated along the Chesapeake Bay, has lots of fun things to do and is an interesting place to explore. It is one of the most scenic towns in the Mid-Atlantic region and has a variety of museums and historic sites as well as great shopping, restaurants, and special events. From touring the U.S. Naval Academy to visiting the Annapolis Naval Museum, there's plenty of things to see and do in this beautiful Maryland city.

01 of 10

Tour the U.S. Naval Academy

Aerial view of the U.S. Naval Academy
U.S. Naval Academy
121 Blake Rd, Annapolis, MD 21402, USA
+1 410-293-1000

Home of the 4,000-strong brigade of midshipmen, the Naval Academy in Annapolis is the training ground for officers of the U.S. Navy and Marine Corps. Additionally, it is home to 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 Naval Academy is located at Randall Street and Prince George Street. Guided tours of the Academy and museum begin here at the Armel-Leftwich Visitor Center.

Along the tour, make sure you don’t miss the renovated chapel and its massive pipe organ. Other major points of interest include the Lejeune Physical Education Center and its Athletic Hall of Fame; Dahlgren Hall and its Drydock Restaurant; and the Bancroft Hall, a dormitory that houses more than 4,400 midshipmen in over 1,700 rooms.

02 of 10

Go Sailing or Powerboating

A Sailboat on Chesapeake Bay
Jeff Weese / Flickr / CC BY 2.0

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, public cruises, boat tours, and private charters are available to take you out on the water, which is 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 even a multi-day excursion aboard a cruise line.

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

03 of 10

Take a Guided Tour of the City

A street view of picturesque Annapolis
Hisham Ibrahim / Getty Images

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

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

04 of 10

Feast on Steamed Crabs

A steamed Maryland crab
Lisa Kling / Getty Images
3030 Riva Rd, Riva, MD 21140, USA
+1 410-956-2784

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 the Navy-Marine Corps Stadium the first Friday in August each year, is recognized as the largest crab feast in the world. Additionally, you can usually find a variety of crabs at the annual Annapolis Seafood Festival, which is held in September each year.

However, if you can't make it to Annapolis in August or September for these events, you can always stop by restaurants like Mike’s Restaurant and Crab House, Cantler’s Riverside Inn, or Skipper’s Pier for some seasonal seafood all year long.

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05 of 10

Tour the Maryland State House

The Maryland State House
Hisham Ibrahim / Getty Images
100 State Cir, Annapolis, MD 21401, USA
+1 410-946-5400
Historic Attractions

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, and the rest of the time visitors can take tours of its historic halls.

The State House is open daily from 9 a.m. to 5 p.m. but is closed on Christmas and New Years Day. To learn about the rich and historic past of the oldest state capitol still in continuous legislative use, guided tours can be requested upon arrival and will begin at the State House Visitors' Center.

06 of 10

Attend an Event or Festival

Jousters perform at the Maryland Renaissance Festival
Richard T. Nowitz / Getty Images
Dock St, Annapolis, MD 21401, USA
+1 410-263-7973

Throughout the year, the residents of Annapolis celebrate everything from the holidays to the city's culture and history, but the summer is certainly the busiest time of year in Annapolis for outdoor festivals and events. Be sure to check the Annapolis Tourism website to learn about all the major annual events.

On weekends in weekends in the summer, be sure to catch the Summer at City Dock music series, which brings street performers and musicians to the Annapolis waterfront for afternoon and evening concerts. Additionally, you can always stop by the first Sunday of each month for an art festival where craft vendors, artists, musical acts, and street performers gather to celebrate the arts.

If you're visiting in the fall and winter instead, 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.

07 of 10

Watch Wednesday Night Sailboat Races

Annapolis Sailboat Race
Greg Pease / Getty Images
2 Compromise St, Annapolis, MD 21401, USA
+1 410-263-9279

Speaking of seasonal events, 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 the 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 a social or first-class dining event in the banquet facilities.

08 of 10

Attend a Sporting Event at the Navy-Marine Corps Stadium

The Navy Midshipmen take the field before the start of a game
Rob Carr / Getty Images
550 Taylor Ave, Annapolis, MD 21401-2220, USA
+1 410-263-4783

Year-round events bring the community of Annapolis together at the state-of-the-art sports facility known at the Navy-Marine Corps 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.

The stadium is located at 550 Taylor Avenue, which is about a mile and a half from the Annapolis waterfront and the United States Naval Academy. However, along with a large parking lot where you can park your rental, you can also take a shuttle bus from the academy to the stadium for major events.

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09 of 10

Take a Bike Tour

Downtown Annapolis and its historic district are both extremely bike friendly, and Annapolis By Bike provides guided tours of some of the best sights in the city throughout the year.

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.

Although you'll need to bring your own bike to take this tour, you can also rent one from Annapolis Velo, one of the best bike shops in town.

10 of 10

Visit the Annapolis Maritime Museum

Signage for the Annapolis Maritime Museum
Smith Collection / Gado / Getty Images
723 2nd St, Annapolis, MD 21403-3323, USA
+1 410-295-0104

The Annapolis Maritime Museum explores the maritime heritage of Annapolis and the Chesapeake Bay with a variety of exhibits and live entertainment.

While there, you can learn about the life of seamen and the seafood industry of yesteryear in the Bay Experience Center, which is housed within the area's last remaining oyster packing plant. Then, you can 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 location on the Chesapeake Bay.

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Top 10 Things to Do and See in Annapolis, Maryland