Historic Maryland State House Tour
Begin your journey at 188 Main Street with your period-attired guide! Embark on a 75-minute tour to explore one of the most historic and architecturally significant state houses in the …
Historic Maryland State House Tour
Begin your journey at 188 Main Street with your period-attired guide! Embark on a 75-minute tour to explore one of the most historic and architecturally significant state houses in the …
Inaugural Corn-Hooley & Shamrock Shenanigans
Don’t miss the Inaugural Corn-Hooley & Shamrock Shenanigans! A fun filled day of cornhole, family fun events, and good ole’ tomfoolery! The Inaugural Corn-Hooley & Shamrock Shenanigans will take place …
Fall Foliage Bay Lighthouse Cruise
This beautiful cruise includes three Chesapeake Bay lighthouses and a spectacular view of the fall foliage along the Annapolis waterfront. Pass under the twin spans of the Bay Bridge and …
Special Historic Hauntings
During the month of October, we’re partnering with Historic Annapolis to offer Special Historic Hauntings. Our spirited guide will lead you through the dark alleys, spooky side streets, and lesser-known …
CYSO Night
Back to CYSO Night is open to the public—whether you’re a returning family, new to the area, or just curious to learn more about what CYSO has to offer. CYSO …
Know Before You Go: A Guide to This Year’s Maryland State Fair
The Maryland State Fair, which takes place over three weekends from August 21 to September 7, is the perfect way to cap off the summer and kickstart the fall. With …
Watermark’s 90 Minute Cruises
Don’t miss Watermark’s 90 Minute Cruises; the Thomas Point Lighthouse Cruise, the Chesapeake Bay Bridge Cruise, and the Scenic Severn River Cruise! Learn more about them here!
Do Not Miss List
Week of 8/21 – 8/27 Presented by Thursday, August 21 – Sunday, August 31 | Midnight Joe Look-Alike Contest | BD Provisions Thursday, August 21 & Friday, August 22 | …
Kent Island Fall Picnic
Don’t miss the Kent Island Fall Picnic on September 28, 2025 from 1:00 pm to 5:00 pm! It will take place at the Kirwan House. Get ready for a great …