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Fun Things to Do in Annapolis, Maryland

One of our very favorite places on the East Coast, the beautiful city of Annapolis often gets overlooked in favor of its larger neighbors like Baltimore or Washington, DC. But there are so many fun things to do in Annapolis, Maryland.

Row of houses flying colorful flags.
Charming Pinkney Street

Annapolis is a waterfront retreat, a vibrant town, and a picture-perfect capital city. It has everything to do from visiting historic sites to wine tasting to sailing the Chesapeake Bay, and a lot in between, too. We visit at least once a year and always enjoy uncovering new things to see. Here’s a look at some of our favorite ways to spend time in the city.

Take a trolley tour

Trolley car with "Discover Annapolis Tours" written on the side.
Ready for a trolley tour

Although a stroll down Main Street gives you a great taste of Annapolis, the capital city is so much more than that. If it’s your first visit, hop on a trolley tour to gain a greater appreciation for all this cute place has to offer

In just an hour, the guide will give you a quick walk through 350 years of history while driving by some of the prettiest buildings around. You’ll see lots of top attractions, including Victorian houses, colonial mansions, views of the Severn River, and the Naval Academy. A trolley tour is one of the best things to do in Annapolis because you see a lot quickly, and it’s easy on your feet, which we always value. Tours leave from the Visit Annapolis Visitors Center.

Visit William Paca House

Tower and decorations in a lush, green garden.
Paca House garden

William Paca was one of Maryland’s four signers of the Declaration of Independence and served as the state’s governor in the 1780s. His 1760s estate now stands as one of the greatest historical places to go in the city.

The Paca House has been painstakingly restored based on historic artwork and evidence found in excavations of the grounds. We enjoyed touring the mansion, summer house, and sprawling two acres of formal gardens, which are certainly worth a stroll, especially on a nice day. Visitors will get an understanding of how the elite lived during the years surrounding the American Revolution, and we loved climbing to the top of the summer house for a view of the beautiful property.

Tour the Maryland State House

Brick building with a large cupola and a statue of a man out front.
Maryland’s distinctive State House

In the heart of Annapolis is the oldest state house in the country that’s still in legislative use. It is historic not only because it was America’s capital for nearly a year in 1783-1784 but because several nationally important events happened here.

The Maryland State House is the place where George Washington resigned as commander in chief of the Continental Army (intending to retire from public life, which didn’t work out so well) and where the Treaty of Paris was ratified. Today, you can visit the Old Senate Chamber on a self-guided tour to see old George dressed in his finest and letting his intentions be known. Washington’s original address is also on display, which is interesting to see.

A stop at the State House is a quick visit and a must for anyone interested in history. It’s open every day except Christmas Day and New Years Day, and visitors are required to show ID and pass through security.

Book a tasting at Great Frogs Winery

Foods for wine and cheese pairing.
Cheese for pairing with the wines

If you’re wondering what to do in Annapolis outside downtown, Great Frogs Winery is a fun place to spend an afternoon. Established in 1999 on an old tobacco farm, the winery takes advantage of the area’s naturally sandy soil to grow French Bordeaux varietals. The grapes are expertly crafted into more than a dozen wines showcasing white, rose, and red varietals and blends.

Bottles of wine at Great Frogs winery in Annapolis MD.
A few Great Frogs offerings

Book a weekend tasting (also Wednesdays and Thursdays in the summer) of their wines and add some cheese and charcuterie to sample the best of what Great Frogs Winery has to offer. Our favorites were the earthy Chardonnay and the spicy Meritage along with some fantastic local brie. When you’re done, have a picnic outside the tobacco barn and wander among the vines.

Visit Banneker-Douglass Museum

Exterior of a red brick church with stained glass windows.
Banneker-Douglass Museum set in a former church

Set in the historic Mt. Moriah A.M.E. Church building, the Banneker-Douglass Museum is Maryland’s official museum of African American history. It is named after Benjamin Banneker, a notable scientist and writer, and Frederick Douglass, who escaped slavery to become one of the most prominent leaders of the anti-slavery movement–both of whom are honored in the museum.

Start on the top floor and work your way down to see the church’s balcony and exhibits focusing on the lives and accomplishments of famous Black Maryland residents ranging from Underground Railroad conductor Harriet Tubman to Supreme Court Justice Thurgood Marshall. We particularly enjoyed the artwork and the section on Herbert Frisby, the second African American to reach the North Pole, who built a whole career on the principle of succeeding at things he wasn’t “supposed to be interested in” because of his race. The small but educational museum is truly a hidden gem.

Allow 60-90 minutes for a visit. It’s free to enter, but donations are accepted.

Stay at the waterfront hotel

6-story building overlooking the water where a sailboat sits.
Annapolis Waterfront Hotel seen from the water

Although it’s hard to believe in a place this attractive, the city only has one waterfront hotel—the appropriately-named Annapolis Waterfront Hotel. It has a serene location right along the harbor where visitors can watch the dance of the sailboats and yachts coming in and out.

We’ve stayed here twice. Upstairs, the rooms are inspired by the setting on the water and have views of downtown or Spa Creek. Downstairs is Pusser’s Caribbean Grille, an outpost of the popular restaurant and bar that made its name far south of here in the British Virgin Islands. Grab a painkiller cocktail and settle in for a lively evening.

Cross the bridge to Eastport

The Eastport flag pictured on a piece of wood with the words, "We like it this way/ Maritime Republic of Eastport."
Eastport insignia at Boatyard Bar & Grill

Just on the other side of the Spa Creek Bridge is the community of Eastport. Technically—the proud residents will have you know—it’s the “Maritime Republic of Eastport.” Founded in 1997 when the drawbridge connecting Eastport and downtown Annapolis was temporarily closed, the “Republic” has its own flag, its own yacht club, and its own sense of community.

Every year, that camaraderie comes out when groups on each side of the water participate in the just-for-fun “Slaughter Across the Water” tug-of-war. In the summer, head to Eastport’s Boatyard Bar & Grill to celebrate with the winners of the Wednesday Night boat races on the Chesapeake, or check out the great waterfront dining any time of the year. As a bonus, there’s no better view of downtown or the Naval Academy than on the Eastport side of the water.

Try a flight at Forward Brewing

The city’s first nanobrewery, Forward Brewing is a must-visit spot in Eastport for beer lovers. With indoor and outdoor seating, the brewery has a lineup of frequently changing small batch craft beers plus a menu that includes soups, salads, sandwiches, and tacos. We’re big fans of their seasonal Oktoberfest lager.

Stroll at City Dock

Boat in the Chesapeake Bay.
Boat parading in Ego Alley

The City Dock is a fun place for people-watching on a nice afternoon. Also known as Ego Alley, it’s the spot for captains to show off their boats and their boating skills as they navigate the narrow area (and the other vessels that are also showing off). Crowds tend to gather by the water to watch the boats come in and dream about buying their own one day.

There are a few seating areas around the dock, or you can watch from the outside seating at nearby The Choptank restaurant (reservations are always a good idea here).

See inside Hammond-Harwood House

Dining room with portraits on its walls and a formal dining table set for dinner.
Hammond-Harwood’s historic dining room

Halfway between the State House and the Naval Academy, the Hammond-Harwood House was built on prime real estate. The elegant colonial home was constructed in 1774, less than a decade before Annapolis became the temporary capital of the United States.

We enjoyed our tour of the home, which is now a National Historic Landmark. It is said to have the most beautiful doorway in Colonial America and features a collection of furniture by John Shaw. Numerous paintings by Charles Willson Peale, one of the most famous portrait artists of the time and a Maryland native, are on display. Check their calendar for special art exhibits and art-focused tours.

The regular guided tour includes the house, garden, and old kitchen. The half-hour version includes a brief ovreview and visit to the first floor of the house. A visit here is best suited for lovers of history, art, and architecture.

Have breakfast at Chick and Ruth’s Delly

People saying the Pledge of Allegiance in a restaurant.
The Pledge of Allegiance at Chick and Ruth’s

There is more than one reason why Chick and Ruth’s Delly is the place to be for breakfast. First is the amazing food, including our favorite “world famous” seasoned crab and cheese omelet. Second is the morning ritual.

Every weekday at 8:30am and weekend at 9:30am, the staff of Chick and Ruth’s assembles for the daily Pledge of Allegiance. Everything and everyone stops for a few brief seconds to salute the flag. It’s so unusual, you almost have to see it to believe it. And, depending on the time of year, you may just find yourself standing next to a state legislator or the governor himself. He has his own booth, after all.

Shop on Main Street

Boutique with clothing and gifts for sale.
One of the cute shops

Main Street is a haven for shoppers. And lovers of good food. And art aficionados. And people who like to relax. This charming area offers a variety of unique boutiques, shops, and galleries you can browse to your heart’s content. When you’re ready for a break, stop at one of the many restaurants, bars, and cafes lining the street.

In particular, we enjoy the unique furniture at Reclaimed of Annapolis and the coastal-influenced artwork at Kim Hovell Fine Art. Pop into Annapolis Shirt Co. for souvenirs or J. McLaughlin for something nice to wear for a night out.

Seek out street art

Geometric street art mural featuring the faces of three men--Abraham Lincoln, Teddy Roosevelt, and James Madison.
Presidents Hill, a Future History Now project in collaboration with Jóvenes Artistas

There are dozens of street art murals to see around town. Primarily clustered around West Street and Main Street, many of the artworks show imagery related to the city’s history or famous Annapolitans. Additionally, a local non-profit called Future History Now works with youth in underserved communities to add meaningful murals every year.

We particularly like the mural featuring activist and former Congressman John Lewis on West Street and the work including both Supreme Court Justices Thurgood Marshall and Ruth Bader Ginsburg on South Street.

Indulge at Annapolis Ice Cream Company

Cup of mint chocolate chip ice cream.
Annapolis Ice Cream Company, a must-visit stop

Annapolis Ice Cream Company is one of our very favorite stops in the city. Made fresh at the shop almost every day, the ice cream here is some of the best you’ll find anywhere.

The Ice Cream Company has 36 rotating flavors made of super-premium ingredients. You know it’s good stuff when it takes forever to melt, even in the heat of the summer. Our favorites are the mint Oreo and pretty much anything with peanut butter, but it’s impossible to go wrong no matter what you try. Don’t be dissuaded if there’s a line–it moves quickly.

Visit the Museum of Historic Annapolis

3-story brick building with rows of windows and a sign for "Museum of Historic Annapolis."
The museum’s historic building

Right on Main Street in a building that dates from the late 1700s, the Museum of Historic Annapolis gives visitors an education on the city’s long history. Over three floors, Annapolis: An American Story tells the stories of revolutionaries, activists, and change-makers who have shaped over 450 years of history.

Artifacts, a film, and lots of displays bring the tales to life, packing tons of information into a small space. Admission is only $7, and the average visit is around one hour. It’s particularly worth it if you’re visiting town for the first time.

Cruise the Chesapeake Bay

Sailboat in the bay.
Sailing on the Woodwind

Don’t miss the chance to appreciate the beautiful Severn River and Chesapeake Bay on a cruise. Two of the most popular ways to get out on the water are on the Harbor Queen (Watermark Tours) or the Schooner Woodwind. A 40-minute cruise on the Harbor Queen gives you a glimpse into the city’s history as you cruise around the harbor, past the Naval Academy, and within view of the Chesapeake Bay Bridge.

On the Schooner Woodwind—a 74-foot wooden schooner—you can participate in their regular 2-hour sails, cruise in search of local lighthouses, or cheer on your boat’s captain in the Wednesday night sailboat races during the summer. If you’re willing, there may even be a chance to pitch in as part of the Woodwind’s crew. Either way, your time on the bay will be fun. We’ve cruised with them at least six times and have loved each one.

Rent your own electric boat

Woman kayaking in Spa Creek.
The view from our electric boat

If cruising the bay with someone else at the helm doesn’t do it for you (or, alternatively, it’s made you completely addicted to the water), be your own captain. Annapolis Electric Boat Rentals offers a unique chance to take one of their boats out on your own. Gather some friends, your favorite snacks, and some beverages, and head out. Cruise Spa Creek, see the waterside mansions of Back Creek, or even take your turn showing off in Ego Alley.

The electric boats can hold up to 11 people—captain included—for a few hours or a whole day on the water. Believe it or not, no previous boating experience is required, and you’ll get a crash course on the spot. What better way to experience the water?

See the Kunta Kinte-Alex Haley Memorial

Sculpture of a man reading to three children.
Part of the memorial

The Kunta Kinte-Alex Haley Memorial stands in a prominent spot beside City Dock. It marks the location where Kinte—an enslaved African and Haley’s ancestor who is the subject of his novel Roots—was brought to the US. It is the only memorial of its kind in the country.

The Memorial consists of three parts—a sculpture that depicts Haley reading to children of different ethnicities, a series of 10 bronze plaques on the nearby seawall, and a 14-foot-wide granite and bronze compass rose. Together, the pieces are meant to convey Haley’s vision of racial reconciliation and healing. Right in the heart of downtown, the memorial is free to visit and always open.

Have tea at the historic Reynolds Tavern

People eating at tables in a Colonial-style dining room with a portrait of George Washington on the wall.
Reynolds Tavern’s popular tea

The history of the Reynolds Tavern stretches back to the colonial era. Since 1747, it has operated as a tavern, rooming house, and meeting spot, among other purposes.

You can still feel the history here when you stop in for a meal. The building functions much as it did 275 years ago, welcoming visitors to its 1747 pub, tearoom, and several upstairs suites and rooms. The décor is reminiscent of colonial times, and they even offer traditional English afternoon tea daily. For a little more space, head to the outdoor beer garden where the stables once stood.

Eat all the seafood

Crabcake sandwich and French fries on a plate.
Crab cake sandwich at Boatyard

Annapolis is known for its seafood. From Maryland blue crabs to Chesapeake Bay oysters and rockfish, there are so many local types of seafood to choose from. We’ve eaten our way across the city several times and have loved every minute. If you’ve ever wanted to try a crab or crack open an oyster, this is the place to do it.

Some of our favorites include the crab cakes at Boatyard Bar & Grill and the incredible cream of crab soup at Carrol’s Creek Cafe.

Tour the US Naval Academy

Monument and canyons in a courtyard.
Monument to four fallen midshipmen

One of the most popular things to see in Annapolis is the US Naval Academy. On a 90-minute tour, guides take you to some of the main sites on the campus of this National Historic Site.

On a Naval Academy tour, you can visit the gym to learn about the Academy’s athletic program and see its Athletic Hall of Fame that includes famous graduates like Roger Staubach and David Robinson. You’ll see Bancroft Hall, the mammoth dorm that houses all 4400 midshipmen, and the statue of Native American warrior Tecumseh. Tours also visit the famous crypt of John Paul Jones, and, most days, there is a stop in the beautiful Naval Academy Chapel.

Black marble crypt.
The crypt of John Paul Jones

Along the way, you’ll learn about the history of the US Naval Academy and the lives of the students who work so hard to be there. We’ve taken the tour three times over the years and always seem to learn something new.

Play around at GameOn

Red brick building with a black and pink sign: "GameOn, bar + arcade."
GameOn Bar and Arcade

Classic video games and a fun, ’90s vibe are even better when you add cocktails. That’s just what you’ll find at GameOn, one of the newer additions to the city.

This combination bar and video game café has arcade games, skeeball, and much more in its location right next to the Graduate Hotel. Try the adult slushies or some “cold ass beer” while you play some Pac Man, Galaga, or classic Connect 4. There are daily specials like half-price game night on Wednesdays or Sunday Family Day where you get 20 free tokens with the purchase of a large pizza before 4pm.

See a show at Rams Head Tavern

Painted red brick exterior of Rams Head Tavern.
Rams Head is a classic

For over 25 years, the Rams Head On Stage has been a mainstay of downtown. Drawing famous comedians, nationally-recognized bands, and other acts with super star power, this venue is a perfect place to see your favorite performer or to discover someone you didn’t know you would love.

Have a meal in the pub before the show (you’ll get a discount) or head straight into the club for dinner and drinks during the performance. We enjoy it here so much that we’ve been unknown to make the trip from our home in Philadelphia just to see a show.

Get crafty at Mission Escape Room

Bright green building with a black and white sign for "Mission Escape Room."
Mission Escape Room

Mission Escape Room is a great place to get your adrenaline flowing. This fun venue has four themed rooms that each operates with a bit of time pressure—you only have 50 minutes to escape. The levels of difficulty range from beginner to advanced and you can experience everything from solving the mysteries of Sasquatch National Forest to investigating fairy tale crimes.

Overhead view of buildings, waterfront, and boats.
Overlooking downtown Annapolis

Where to Eat
For a town with a compact center, Annapolis is absolutely full of amazing restaurants. Here are some of our favorites.

Iron Rooster: The spot for breakfast or brunch, with homemade pop tarts and eggs Benedict
Carrol’s Creek: Variety of seafood options with gorgeous waterfront views
Miss Shirley’s: Serving breakfast, lunch, and brunch with a hefty dose of Southern hospitality

Where to Stay (If you book through these affiliate links, we may earn a small commission (at no extra cost to you).
Annapolis Waterfront Hotel: Sophisticated design in a comfortable environment with a harbor view
Westin Annapolis: Heavenly beds and the amenities you expect from Marriott plus an indoor pool.
Crowne Plaza Annapolis: Comfortable rooms at a great value

One of our early visits was sponsored by Visit Annapolis. All opinions of the charming and fun are our own.

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Ma Eden

Wednesday 29th of June 2022

Wow, very good picks. Can someone help me, pls. Hubby and I plan a Summer day's visit, no overnight stay. Can we visit most of these interesting places in a day's time? We would love to have breakfast @Chick & Ruth's for the "morning ritual" or maybe @Iron Rooster? The trolley tour sounds interesting and I find it a must. Are these places in walking distance from each other? Where should we park at?

Ma Eden

Friday 1st of July 2022

@Laura Longwell, thank you for the info. I'll try to get a tourist map, if something like that is available.

Laura Longwell

Thursday 30th of June 2022

Most of the places are within walking distance in the downtown area, but Great Frogs would require a drive. There are quite a few parking garages/lots along West Street that would be conveniently located.


Monday 25th of April 2022

But the best is Forward Brewery, in Eastport!


Friday 28th of October 2022

@Willard, my hubby and I heading to Annapolis Monday late morning… I loVe a great Bloody Mary…drinking … we both loVe seafood… the water… the view .. fishing perhaps …(if they’re biting) staying overnight…what do u suggest

Cheryl Donnelly

Sunday 10th of April 2022

As a local I had no clue about the electric boats!! Sounds like a great idea for sharing with out of town visitors . Thanks very much.

Laura Longwell

Monday 11th of April 2022

Thanks, Cheryl. This is our favorite type of comment to get because we always try to uncover some lesser-known things. We're not locals, but as Philly residents, we come to Annapolis a lot, and we love your city :)

Ruth ward

Saturday 15th of January 2022

Memory lane for me. Stationed at Academy 1975-6. Was steward in Kings Hall. Rickets Hall was barracks for me. When off duty strolled through streets if old Annapolis.


Sunday 9th of January 2022

Great! we are going to experience this spring. Thanks Carol.

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