Fall Events in Annapolis
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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.
Fall Events in Annapolis
The fall is a great time to come to Annapolis! Skip the pumpkin patch and get out on the water. Discover one of the prettiest towns for fall activities with the kids around the DMV. Plan your Pirate Adventure when the weather is perfect and enjoy a day in Annapolis with one of the many fall events in Annapolis. Pirate Adventures offers up to six sailing times on Saturdays and Sundays in September and October. We recommend reservations for this popular event. Join us on the pirate ship Sea Gypsy as we search for sunken treasure, fire our water cannons at an enemy pirate and enjoy the beautiful views of Annapolis from the water. The town of Annapolis is busy in the fall with festivals and events, we have listed our top pics below. We hope to see you in Annapolis this fall!
Pirate Adventures on the Chesapeake
Age appropriate for kids ages 3-10 this is a can’t miss attraction for families. Kids get dressed up and facepainted and live the life of a pirate aboard the pirate ship Sea Gypsy. Our fall season includes special events to celebrate the fall season. Find out about our Princess and Pirates cruise or Pirate Pete’s Pumpkin Patch here.
Navy Football
The Navy plays in Annapolis on 9/14, 10/5, 10/19, 10/26, and 11/23. Check out the Navy football schedule here. Join us on a Pirate Adventure in the morning and then head over the stadium for tailgating before the game.
Fall Sailboat and Powerboat shows
Come to see city dock turned into the worlds largest in water boat show. Bring the kids on a Pirate Adventure and then take them over to the boat show to google at a pirate ship of your very own! We provide free parking for the day for our customers and you can take the water taxi over to the boat show.
The Maryland Renaissance Festival
The Maryland Renaissance Festival runs weekends through October 20th. Located in Crownsville, a 10-minute drive from Annapolis, you can spark the kid’s imagination if you combine a trip to Pirate Adventures with the Renaissance festival. September 28th and 29th is pirate’s weekend at the Renaissance Festival. Join us this fall and celebrate help celebrate the best time in Annapolis!