17 Cool Things to Do in Annapolis On Your Maryland Vacation

Heading to Maryland for your next vacation? Annapolis, resting on the shores of the Chesapeake Bay, should be high on your list. Time stands still in this historic city, once a colonial seaport and the nation’s first peacetime capital city. For history buffs and water lovers alike, there are plenty of things to do in Annapolis, Maryland.

In Annapolis’s historic district, centered around the magnificent domed Maryland State House, quaint brick-lined streets showcase beautiful examples of 18th-century architecture. The United States Naval Academy and an array of interesting museums and galleries tell the story of the centuries-old port town.

Known as America’s Sailing Capital, Annapolis is a paradise for water lovers. Sleek sailing vessels line the marina as the sound of tinkling yacht masts floats on the breeze.

Not sure where to go and what to do in this beautiful Maryland port city? Read on to discover all the best places to visit in Annapolis, MD.

Why Treksplorer? Founded in 2011 by Ryan O’Rourke, Treksplorer provides travel recommendations and advice to millions of readers every year. Our content is rooted in our writers’ firsthand experiences, in-depth research, and/or collaborations with other experts and locals. Read more about our editorial policy.

Annapolis Maritime Museum & Park

There’s no better place to learn about the rich maritime history of Annapolis than at the Annapolis Maritime Museum & Park. The state-of-the-art museum, based in an oyster packing plant on the shores of Back Creek, offers an incredible collection of exhibits.

Learn all about the history of boat building and how the city was once the bustling center of seafood exportation after the Revolutionary War. At the massive 850-gallon aquarium, you can explore the ecosystem of an oyster reef and oyster-shucking industry. You can also see authentic oyster boats and how they were constructed and take a tour of one in the bay.

Don’t miss the 1868 Oyster Wars Cannon, used by the Maryland State Oyster Police to fend off pirates during the Oyster Wars. When you’re done, take a stroll along the beautiful beach in front of the Annapolis Maritime Museum and soak up the views.

William Paca House & Garden

Step back in time to the 18th century at the William Paca House & Garden and marvel at the glorious architecture and beautiful gardens. The historical house was once the home of William Paca, one of the signers of the Declaration of Independence and state governor in the 1780s.

William Paca House & Garden

Built in the mid-1700s, this beautifully preserved Georgian manor house is now one of the finest 18th-century homes in the United States. Explore William Paca House & Garden on a guided tour and take in the handsome period furnishings and alluring art collection.

After the tour, ramble through the lovely grounds. They feature five formal and terraced gardens and a fragrant kitchen garden filled with herbs, fruit, and vegetables. You’ll also find a medicinal herb garden, lush water gardens, topiaries, and plenty of shaded benches to take a break.

Annapolis City Dock

Mosey on down to the Annapolis City Dock, where you’ll discover a wealth of entertainment for the whole family. Charming little gift shops with handcrafted goods rub shoulders with locally owned fashion boutiques, quirky art galleries, and historic inns. There are also plenty of restaurants, eateries, and bars with lovely views over the Chesapeake Bay.

Annapolis City Dock

Known as the heart of historic Annapolis, the City Dock has a deep connection with the water. Kick back and relax at one of the dockside cafés and watch the parade around the turning basin of Ego Alley. Explore the dock on a harbor tour or test your skipper skills at the helm of the graceful Schooner Woodwind.

U.S. Naval Academy Museum

Annapolis is synonymous with the United States Naval Academy. And a trip to the city is never complete without a visit to the U.S. Naval Academy Museum. Established in 1845 to honor the heritage of the U.S. Navy and Marines, the museum has some remarkable exhibits worth exploring on a guided tour.

U.S. Naval Academy Museum

The 90-minute tour of the U.S. Naval Academy Museum will take you to all the main sites, including the famous crypt of John Paul Jones and the enchanting Naval Academy Chapel. Marvel at tiny model ships that were constructed at the same time as their full-sized counterparts. Gaze at the statue of Native American warrior Tecumseh.

The U.S. Naval Academy Museum is great for kids, and the guides are wonderful at engaging them. It’s a great way to learn more about the importance of the Academy’s program and its vital role in protecting the nation.

Jonas and Anne Catharine Green Park

Feel like fishing, strolling along sandy beaches, and relaxing with the family over a picnic? Jonas and Anne Catharine Green Park is your best bet while visiting Annapolis. Simply known as Jonas Green, this small park is one of the city’s hidden gems.

Located on the banks of the Severn River, the park is named after colonial-era Annapolis residents Jonas and Anne Catharine Green, both of whom were publishers of the Maryland Gazette. Jonas and Anne Catharine Green Park offers some of the best fishing in the area; be sure to pack a few rods to cast in a line.

If you have a boat, you can launch off a little beach in the park. There are plenty of picnic tables and benches for setting up camp. The beach is also ideal for launching watercraft such as canoes, kayaks, stand-up paddle boards, and windsurfing boards.

Sandy Point State Park

Another lovely place for enjoying the beach and picnicking around Annapolis is Sandy Point State Park. Offering gorgeous views over the Chesapeake Bay, this is an ideal spot to spend the day relaxing. The 786-acre park has several beautiful beaches and picnic areas, as well as over four miles of hiking trails for all ages and skill levels.

Sandy Point State Park

Sandy Point State Park is also home to the historic Sandy Point Farmhouse if you feel like taking in some history while you are there. Built for John Gibson in 1815, this charming 18th-century style historic home is a beautiful example of Maryland domestic architecture.

While you are sunbathing on the beach, keep an eye out for migratory birds. Many species travel past the park on the ‘Eastern Flyway’ en route to Europe. If you want to find out more about the pathway and the birds that use it, there’s an excellent nature center and interpretive center in the park.

Hammond-Harwood House

Architecture lovers will delight in the Hammond-Harwood House, an outstanding example of late colonial architecture. Designed and built in 1774 by William Buckland, this historic home has been lovingly maintained to keep it in its original state. It has a notable art collection and one of the most beautiful doorways in Colonial America.

Hammond-Harwood House

Take a tour of the Hammond-Harwood House to marvel at the intricate details, such as the floor construction using horizontal pegs and a portrait of George Washington painted by Charles Willson Peale. You’ll also see a fine portrait of William Buckland’s daughter holding a doll and the actual doll on display.

After your tour, enjoy a quiet stroll around the manicured gardens.

Banneker-Douglass Museum

Explore the rich African-American history of Maryland with a visit to the Banneker-Douglass Museum. Based in a historic church building on Franklin Street, the museum promotes African American culture and history through an outstanding array of exhibits and collections.

The museum is named after Benjamin Banneker and Frederick Douglass. Benjamin Banneker was a notable scientist and writer, while Frederick Douglass was a distinguished leader of the anti-slavery movement.

Exhibits at the Banneker-Douglass Museum focus on the tragedy of slavery, as well as the accomplishments of those who fought against it.

Learn the story of subway conductor Harriet Tubman and Supreme Court Justice Thurgood Marshall. Immerse yourself into the African American culture of Maryland through art, history, and music.

Quiet Waters Park

Quiet Waters Park is a lovely family-friendly park with a wealth of activities for the whole family. Spanning 340 acres, the park has several hiking trails winding their way through grassy meadows and shady forests. You’ll also find six miles of paved trails for cycling and jogging.

Pack a picnic basket and find a spot on the banks of Harness Creek or the South River, both of which run through the park. There’s an overlook perched above the South River that offers beautiful views of the river and the surrounding landscapes.

Quiet Waters Park

If you are traveling with Fido, you can take him along; there are two fenced dog parks and a dog-friendly beach. A large playground will keep the little ones occupied, and a small marina rents out canoes, kayaks, and other types of watercraft if you fancy a paddle.

Pop into the visitor center, where you’ll find an art gallery showcasing local artists’ works and a charming café that serves locally sourced fare.

Maryland World War II Memorial

Take some time out to marvel at this dramatic, modern memorial dedicated to all the Marylanders who lost their lives in World War ll. Designed by New York architect Secundino Fernandez, the Maryland World War II Memorial rests atop a hill overlooking the Severn River.

Maryland World War II Memorial

The open-air amphitheater is surrounded by 48 rectangular granite columns, each representing the states involved in the war. Take a closer look, and you’ll see several symbolic elements, tributes, and milestones relating to the war.

Other inspiring features of the Maryland World War II Memorial include two 14-foot-wide globes showing the locations of the key battles during the war. A striking steel column has seven sides representing Maryland as the seventh state in the Union. It’s topped with a star that’s illuminated at night to create a breathtaking scene.

Historic London Town & Gardens

Take a day trip out of Annapolis and head to Edgewater, a short drive away, to visit Historic London Town and Gardens. Step back in time to 18th-century London Town, a bustling settlement and important trade junction at a crossing point in the South River.

Wander around the old town and learn about its rich history from costumed interpreters. Explore both original and reconstructed buildings in Historic London Town to get a feel for life in the city in the late 1700s. Visit the Carpenter’s Shop and the Lord Mayor’s Tenement. Check out the William Brown House, once a tavern and later an almshouse.

The gardens at Historic London Town and Gardens are a delight with a variety of landscapes like a woodland garden, a manicured ornamental garden, and a Sound and Sensory Garden that the kids will love.

Great Frogs Winery

If the name of Great Frogs Winery doesn’t pique your interest, their wines certainly will. This popular winery is a lovely place to spend an afternoon if you have a few hours to spare. Located at Harness Creek Vineyards, Great Frogs Winery has produced rustic, artisanal wines for over 20 years.

Surrounded by the waters of Chesapeake Bay, the wines at Great Frogs Winery are influenced by the rich maritime history of Maryland’s capital. The sandy soils of the area are ideal for growing French Bordeaux varietals. The estate produces more than a dozen wines in white, rose, and red varietals.

Head to the estate on a Saturday to enjoy a tasting of their award-winning wines against a backdrop of beautiful views. Don’t forget to stock up when you leave!

Pennsylvania Dutch Farmer’s Market

Everyone loves a great farmer’s market, and the Pennsylvania Dutch Farmer’s Market won’t disappoint! Known locally as the ‘Amish Market,’ the market is based at the Annapolis Harbour Center. It runs from Wednesday through Saturday.

What’s unique about the Pennsylvania Dutch Farmer’s Market is that everything in the market is made by the Amish community in Lancaster County, Pennsylvania. Fresh produce, herbs, and flowers are grown, and meats are hand-raised in the heart of Amish country. Cooked foods are made using traditional Lancaster County recipes that have been handed down through generations.

Stock up on everything you need for your holiday, from fresh fruit and vegetables to cheeses, meats, and salads. When you have worked up an appetite, head to the Dutch Market Restaurant for a delicious Amish meal. Take a slice of Lancaster County home with you with a piece of handmade solid hardwood furniture from Millwood Furniture.

Thomas Point Park

Looking for a lovely little park for a quiet afternoon surrounded by nature? Check out Thomas Point Park, set on the shores of the Chesapeake Bay near Fishing Creek. Offering beautiful views over the water, the park is best known for its fishing. There are plenty of shady spots near the water to cast a line here.

Thomas Point Park has lovely grassy areas for picnicking and a pavilion if you want to have a crowd. It’s also a great spot to bird watch. You’ll see plenty of migratory waterfowl in and around the water. The spectacular panoramic scenery of the Chesapeake Bay area is alone worth a visit!

Federal House Bar & Grille

Time to eat! If you’re looking for a comfortable, fuss-free, and laid-back place to eat, head to the Federal House Bar & Grille. Located on Market Space in the Historical District of Annapolis, this casual restaurant is perfectly placed to enjoy a meal after shopping or sightseeing. Grab a shaded table outside and sit and watch the world go by over a cold craft beer.

The menu at Federal House Bar & Grille features typical New American tavern fare. You’ll find everything from soups and salads to sandwiches and steaks. The restaurant also serves breakfast and brunch with a few of the favorites – think Eggs Benedict and breakfast tacos. Drinks-wise, you’ll enjoy a selection of craft beer, wine, whiskey, and bourbon.

Maryland State House

Immerse yourself in American history with a visit to the beautifully preserved Maryland State House. Built in 1779, the former state house has seen many important historical moments. In 1960, it was designated a National Historic Landmark.

Maryland State House

The best way to see Maryland State State is on a self-guided tour. Join in to learn how it once served as the capital of the fledgling United States of America. George Washington also left his post as commander of the Continental Army here. The ratification of the Treaty of Paris was undertaken here, officially bringing the Revolutionary War to an end.

The Maryland State House’s wooden dome dates back to 1794 and is the oldest in the country. Marvel at the old wood-and-plaster construction in the lobby, observing the difference between the newly added stately marble columns and walls. Make your last stop the Old Senate Chamber to see George Washington dressed in his finest.

Chase-Lloyd House

Another fascinating slice of history to explore in Annapolis is the Chase-Lloyd House on Maryland Avenue. This beautiful Georgian mansion was once owned by Samuel Chase, one of the signers of the Declaration of Independence.

Built in the late 1700s, the Chase-Lloyd House is one of the finest examples of Georgian architecture in Maryland. It also boasts elegant interiors designed by William Buckland of Hammond-Harwood House fame.

Chase-Lloyd House is also named for the wealthy plantation-owning Lloyd family. They purchased the house from Samuel Chase and lived there for many generations.

The house is open for tours between March and December. It’s one of the best things to do in Annapolis, MD, if you enjoy American history and Georgian architecture.


Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

DISCLAIMER: Treksplorer is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com and its affiliated international sites.

DISCLAIMER: You'll notice that from time to time I link out to recommended hotels/tours/products/services. If you purchase anything through these links, I'll receive a commission. It won't cost you anything extra, but it will help keep me trekkin' on and delivering more free (and unsponsored!) travel information to you. Thanks :)