50 Things to Do in Annapolis
Find Family Fun at Pirate Adventures
Set sail in search of fun with us and experience a Pirate Adventure with your family aboard the pirate ship Sea Gypsy in the Annapolis Harbor.
50 Things to Do in Annapolis
Looking to explore Annapolis today? There are so many unique things to do in Annapolis and we hope this list will inspire first time visitors to our great city as well as lifelong residents to explore all there is to do here in Annapolis. Browse our list and start planning your great day in Annapolis, add to our comments section with your favorite things to do in Annapolis.
Things to Do in Annapolis with Kids
As a company that serves as a family attraction in Annapolis we thought we would start the list with fun things for kids and families in Annapolis.
- Search for sunken treasure, fire the water cannons. Take your kids on the pirate ship Sea Gypsy in the Annapolis Harbor for a Pirate Adventure.
- Try stand up paddleboarding with your family at Annapolis Canoe and Kayak
- Get some seafood at one of our many family friendly restaurants
- Stop for ice cream at Storm Brothers or Annapolis Ice Cream Company
- Feed the ducks at City Dock
- Ride the water taxi
- Hit the beach and get great views of the Bay Bridge at Sandy Point State Park
- Paint your own pottery at Clay Bakers on Main Street
- Pledge allegiance at Chick and Ruth’s Delly
- Hit a playground in Annapolis
Looking for more things to do in Annapolis with kids? Check out our article: What to do with kids in Annapolis
Things to do in Annapolis as a First Time Visitor
When coming to Annapolis for the first time don’t miss these experiences that make our city so special.
- Catch Noon Formation at the Naval Academy
- Drink a painkiller at the dock bar at Pusser’s
- Get out on the water
- Learn about the history of Annapolis from the water by kayak with Kayak Annapolis, LLC
- Sail away on the Schooner Liberte
- Catch the Wednesday Night Sailboat Races from City Dock, the Naval Academy, or the Spa Creek Draw Bridge
- Take in a show under the stars at the Annapolis Summer Garden Theater
- Take a walking tour through the historic streets with Capital City Colonials
- See a concert at Rams Head Tavern
- Get your shopping fix on Main Street and Maryland Avenue
Things to do in Annapolis for a special event
Street festivals, parades and special events are always happening in Annapolis. Don’t miss the best of what our town has to offer with these special events.
- Celebrate the holidays in a uniquely Annapolis way with the Eastport Yacht Club Lights Parade.
- Buy a boat, or dream about buying a boat at the Annapolis Boat Shows
- Check out the craft vendors, street performances and musical acts at the First Sunday Arts Festival.
- Celebrate your Irish Heritage with the St. Patrick’s Day Parade or the Annapolis Irish Festival.
- Catch Annapolis’ local music festival with Eastport A Rockin‘
- Celebrate the Blues at the Chesapeake Bay Blues Festival
- Celebrate Spring with the Annapolis Oyster Roast and Sock Burning
- Crack crabs at the World’s Largest Crabfeast put on by the Rotary Club of Annapolis
- Wear your biggest hat and break out the bow ties for the St. Johns – Naval Academy Annual Croquet Match
- Experience the Annapolis dining scene with Annapolis Restaurant Week
Things to do in Annapolis to celebrate History and Architecture
Find out why the Historic Annapolis Foundation calls Annapolis “A Museum Without Walls” Take a historical walk through town and back through time. Don’t miss these spots that celebrate our American History.
- See the Kunta-Kinte Alex Haley Memorial at City Dock
- Visit Middleton Tavern – one of the oldest continuously operating taverns in America
- Check out the Maryland State House – America’s oldest state capital still in use
- See the Most Beautiful Doorway in America at the Hammond Harwood House
- Visit a house once occupied by a signer of the Declaration of Independence with #s 5,6, and #7 on the list.
The William Paca House and Gardens
- The Chase-Lloyd House
- The Charles Carroll House
- Tour the Historical Annapolis Foundation Museum
- See the first place of worship in Annapolis at St. Anne’s Church
- Visit Naval Academy Chapel and the Crypt of John Paul Jones.
Things to do in Annapolis: Parks and Wide Open Spaces
- Visit the heart of Annapolis and watch the boats turn around in Ego Alley at City Dock
- Take in views of the South River from Quiet Waters Park
- See Thomas Point Light House from Thomas Point Park
- Check out the twin spans of the Bay Bridge from Sandy Point State Park
- Launch your boat, canoe or kayak from Truxtun Park
- Have a picnic on the Severn River at Jonas Green Park
- See Annapolis and the Naval Academy from the top of the hill at the Maryland World War II Memorial
- Ride your bike on the rail trail at the Baltimore Annapolis Trail Park – starts at the World War II Memorial
- Find a quiet place to soak in the sites of Annapolis at one of our many street end parks
- Venture a little further out of town to Historic Londontowne and Gardens
We hope you have found enough reasons to come and visit us in Annapolis. Wave to the pirate ship when you see us pass City Dock this summer and leave us a comment with your favorite things to do in Annapolis!
Great website full of lots of informations! As a new visitor to Annapolis I will be returning to this site frequently……and definitely will cruise on The GYPSY for a pirate adventure! See you soon:)
Welcome to Annapolis! Hope to see you this season on the high seas.