Annapolis Activities: How to Experience Maryland’s State Capital

Annapolis may be known as a sailor’s haven, but the city also offers fun things to do for different age groups and interests. From venturing outside to sampling Maryland’s blue crabs and browsing boutiques, it’s easy to plan an adventure here. For some ideas, here are the top Annapolis activities to try during vacation.

Popular Annapolis Activities to Try in Maryland

annapolis outdoor recreation vacation

Enjoy the Great Outdoors

As the Sailing Capital of the U.S., Annapolis has a stellar reputation for water recreation. The city’s location on Chesapeake Bay and more than 500 miles of waterways provide a perfect playground for outdoor adventure. Enjoy boating, canoeing, kayaking, SUP, relaxing on beaches, fishing and sailing.

To spend time on the beach, head to Sandy Point State Park. This park measures 786 acres, and welcomes visitors to relax and enjoy picnics together. Quiet Waters Park provides a place to walk trails, admire nature and even ice skate during winter. For everything boats, visit Ego Alley. This gathering spot has tons of boats, restaurants and people-watching opportunities.

Take a Tour

Annapolis offers way more than a charming coastal destination. The area features hundreds of years of history, maritime culture and even pirate adventures.

One of the best ways to see the entire area is to book a trolley tour. Options last about an hour and provide an easy way to sight-see, learn, and take photos. For a more personalized experience, schedule a guided tour of U.S. Naval Academy. The school serves as the top attraction in Annapolis, and welcomes all ages to hear true stories, browse exhibits and admire architecture.

Other Annapolis tour options include ghost walks, helicopter rides, food crawls, scavenger hunts, boat charters and pirate cruises.

annapolis activities food adult

Eat and Drink

Most foodies come to Annapolis to try famous Maryland’s blue crabs and crab cakes. However, there’s much more to eat after the crab. Annapolis’ food scene has casual and upscale waterfront dining, homemade pizzas, bakeries, hearty comfort food, fresh and light dishes, steakhouses, and international cuisine.

In addition to delicious food, the city also has local drink options. Beer lovers enjoy sampling Chesapeake Brewing Company. Wine tasters should visit Great Frogs Winery. For additional options, take a ferry to nearby St. Michaels, which has breweries, distilleries and wineries. Those just looking for a hangout will find bars, clubs and pubs on Main Street and in Eastport.

Shop for Local Goods

Whether supporting local small business owners or indulging in retail therapy, shopping ranks among the top Annapolis activities list.

Start downtown. This walkable area is lined with boutiques, art galleries, antique shops and souvenirs. Additionally, shoppers can customize the experience by visiting one of Annapolis’s five neighborhoods.

For big names and designers, Westfield Mall and Annapolis Town Centre at Parole has hundreds of stores, restaurants, and services. The town center also hosts community events, outdoor concerts and fashion shows. For major discounts on designer brands, take a short drive to Arundel Mills in Hanover.

annapolis activities downtown

Stroll Downtown Annapolis

Not into shopping? No problem. Downtown Annapolis also serves as a gateway to the city’s top attractions. The State Circle and Maryland Avenue provide a glimpse into the city’s history. Just don’t forget to stop at Maryland State House. This attraction is the oldest U.S. State capitol building in continuous use and dates to 1772.

Day-trip to the Islands

Ranked among the top Annapolis activities is day-tripping to nearby islands. To narrow down the options, Kent Island and St. Michaels rank among the most popular.

Kent Island sits across Chesapeake Bay. Here visitors love outdoor sports, fishing, riding bicycles, tour historic sites and shopping. St. Michaels sits tucked away in Eastern Bay. This small town ranks among some of the best coastal destinations in Maryland.

maryland sites history

Visit Museums and Sites

Residents and business owners work to preserve the area’s rich history while celebrating what makes it such a special destination. Even better, guests will find museums and historic sites open for tours.

Museum options include Annapolis Maritime Museum and Park, Hammond-Harwood House, Chesapeake Children’s Museum, Wiley H. Bates Legacy Center and U.S. Naval Academy Museum.

Additional sites feature historic homes and gardens, showcase influential people, and help visitors step into another time. Noteworthy stops include Willam Paca House and Garden, Banneker-Douglass Museum and Hammond-Harwood House

Extend the Trip

If all this isn’t enough to do in Annapolis, Baltimore and Washington D.C. are located less than a one-hour’s drive. Both cities offer famous attractions, museums, family-friendly activities and neighborhoods to explore. This makes it easy to take a day-trip to National Mall, National Aquarium, National Cathedral, Inner Harbor and hundreds more attractions.

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