7 Best Things to Do in Beautiful Annapolis, Maryland

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The beautiful waterside city of Annapolis is not only the capital city of Maryland, but is also a popular tourist destination due to its multitude of things to do, both on the water and on land. From its quaint historic district to the waterfront grounds of the United States Naval Academy, there is beauty to be taken in everywhere you look. Plus, there’s plenty of restaurants, shopping and nightlife to top it off!

Tour the U.S. Naval Academy
Bancroft Hall at USNA is the largest college dormitory in the world.

Tour the U.S. Naval Academy

Perhaps one of the most historic and majestic things to see in Annapolis is the United States Naval Academy. Since 1845, this undergraduate school has been preparing men and women (since 1976) for careers in the U.S. Navy and Marine Corps. The campus, which is a modest 340 acres in comparison to other military academies, features many beautiful buildings including the ornate Naval Academy Chapel and Bancroft Hall – the largest building at the Academy and the largest college dormitory in the world. Although many of the buildings are not open to the public, you can take a public walking tour led by a professional, certified guide and see Bancroft Hall, Memorial Hall, the Main Chapel, the statue of Tecumseh (which was presented by the class of 1891) and the crypt of Naval war hero, John Paul Jones. Make sure to also check out the USNA Museum, which features two floors of exhibits documenting the history of the U.S. Navy and the Academy.

Walk Around the Historic District
You can learn about more than 300 years of history in downtown Annapolis.

Walk Around the Historic District

No visit to Annapolis would be complete without visiting its beautiful historic district. The city’s history goes back more than 300 years and you can learn all about it by taking a guided or self-guided tour beginning at the city’s Visitor Center. You can also download an app for your smartphone that will lead you on a tour of the city and tell you all about its colonial, maritime and African American history. Some of the main sites you’ll want to check out include the Annapolis Maritime Museum, the Maryland State House – the country’s oldest state house to be in continuous use, and the Banneker-Douglass Museum, the state’s official African American heritage museum.

Get Out on the Water
Experience the beauty of the Chesapeake Bay from on-board a sailboat.

Get Out on the Water

Since Annapolis located right on the Chesapeake Bay, there are plenty of ways to enjoy the water if you’re visiting during the warm months. Try your hand at stand-up paddleboarding, go windsurfing or kayaking, or take a ride on the mock pirate ship, the Sea Gypsy. Kids will especially love this immersive experience that includes costumes, props and a search for sunken treasure! The grown-ups will also want to check out the “boat and breakfast” experience that includes a stay aboard a 75-foot sailing yacht, complete with a two-hour sunset sail on the Chesapeake Bay, dinner at a dockside restaurant and breakfast on the water the next morning.

Taste the Deliciousness at the Amish Market
You'll find 290,000 square feet of homemade goods at the Amish Market.

Taste the Deliciousness at the Amish Market

Located in the 290,000 square foot Annapolis Harbour Center in historic downtown Annapolis, the Pennsylvania Dutch Farmer’s Market (also known as the Amish Market) is a massive collection of delicious, homemade products from the Amish merchants of Lancaster, PA. The traditional Pennsylvania Dutch recipes for these goods go back through the generations and include salads, snacks, desserts, cheeses, chemical-free meats, fried chicken, fresh produce and even candy and ice cream. You’ll also find a selection of beautiful, handmade wood furniture and the Dutch Market Restaurant, which serves breakfast, lunch and dinner made by Amish cooks using traditional Pennsylvania Dutch recipes.

Sip Some Wine at Great Frogs Winery

The name may sound a little silly, but their wines are nothing to laugh at. In fact, Great Frogs Winery has won multiple awards for their wines including three bronze, five silver, two gold and a double gold at the 2017 Grand Harvest Challenge held in Sonoma County, CA. That’s because the owners are hands-on through every step of the process from pruning to harvesting. They are only open on Friday and Saturday and their tastings are by appointment only, so make sure to call ahead or reserve your space online.

Go on a Seafood Crawl

Sure, you’ve probably heard of a bar crawl… but have you ever heard of a seafood crawl? This unique, two-hour culinary tour of Annapolis consists of a ride aboard a six-person eCruiser, where you’ll learn all about the city of Annapolis and nearby Eastport, while making stops at four local restaurants where you’ll sample everything from mussels and clams, to oysters and rockfish.

Enjoy Nature at Quiet Waters Park
The ice rink at Quiet Waters Park is open for both free skating and skating lessons.

Enjoy Nature at Quiet Waters Park

If you’re in the mood for a little peace and quiet, take a stroll on one of the winding trails at Quiet Waters Park and enjoy the beautiful scenery. There’s also a Visitor’s Center where you can browse art exhibitions from local artists, picnic areas for enjoying a meal and an outdoor ice skating rink that is open for both free skating and ice skating lessons.

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