Saturday October 25th and Sunday 26th Kids in costume cruise FREE on our Harbor cruises in Annapolis and Baltimore-(Walk Ups only) Post your onboard costume photo and tag @Watermark and #HarborHauntsto win a family Holiday Cruise. $25/Adult kids in Costume cruise FREE for more dates and information visit https://watermarkjourney.com/events/annapolis-harbor-usna-cruise/

Join us for a candlelit program that conjures the shadowy musical world of haunted harbors, shipwrecks, and sailor’s lore. Below Deck draws from the rich tradition of maritime music sung aboard tall ships and in dockside taverns during the long 18th century. Sea shanties—rhythmic, call-and-response work songs—were used to coordinate physical labor aboard sailing vessels, […]

During the month of October, we’re partnering with Watermark Tours to offer Special Historic Hauntings Tours on Thursdays, Fridays, and Saturdays at 7:30 pm. Our spirited guide will lead you through the dark alleys, spooky side streets, and lesser-known haunted sites of the old and creaky town of Annapolis. Hear from real diary entries and newspaper […]

Saturday October 25th and Sunday 26th Kids in costume cruise FREE on our Harbor cruises in Annapolis and Baltimore-(Walk Ups only) Post your onboard costume photo and tag @Watermark and #HarborHauntsto win a family Holiday Cruise. $25/Adult kids in Costume cruise FREE for more dates and information visit https://watermarkjourney.com/events/annapolis-harbor-usna-cruise/

MD Concert Series Presents... Big Buffett Beach Band Sun, October 26, 2025 3PM Hammonds Lane Theatre $10 - $25 | $1.30 - $1.75 Fees This large band with horns, percussion, drums, bass, keyboards, and multiple guitars is the complete Jimmy Buffett experience. The Sons of Pirates first launched as a Buffett tribute group, but has […]

In October, experience a spirited tour of the historic William Paca House, highlighting tales of the past: sickness, treatments, mourning rituals, and superstitions. Tours are offered every Saturday at 2 pm and every Monday at 11 am throughout October. You’ll be guided by candlelight on a special tour focusing on the treatment of diseases, medical practices […]

READ Emma – TOUR Hammond-Harwood House – DISCUSS with fellow readers! Participants will enjoy a 60-minute guided tour of the house that compares the customs and social graces of the Loockerman family, who lived in the Hammond-Harwood House in the early 19th century, with those of characters in Jane Austen novels. A book club discussion […]

Historic Annapolis and the Maryland Historical Trust invite you to attend the 2025 Orlando Ridout V Memorial Lecture at the Governor Calvert House. The lecture is free, but reservations are required, and we thank you for considering a donation when you register to support this lecture series. This year, we are pleased to welcome Philadelphia […]

Do you dare to join us as the sun sets, and the shadows grow long while we tell long forgotten stories of London Town's darker side? Learn about the Pirate Clark, the plague of mad dogs, and about 18th-century ghost stories. Hear some of London Town's historical oddities on a 45-minute specialty tour. This is […]

During the month of October, we’re partnering with Watermark Tours to offer Special Historic Hauntings Tours on Thursdays, Fridays, and Saturdays at 7:30 pm. Our spirited guide will lead you through the dark alleys, spooky side streets, and lesser-known haunted sites of the old and creaky town of Annapolis. Hear from real diary entries and newspaper […]

Step aboard the historic Skipjack Wilma Lee for a special Halloween sunset cruise on the Chesapeake Bay. Enjoy a crisp autumn evening on the water with friends, festive vibes, and a touch of Halloween magic. We will serve a selection of spooky halloween goodies along with beer, wine, and canned cocktails. Costumes are welcome and encouraged. Captain Rick […]

During the month of October, we’re partnering with Watermark Tours to offer Special Historic Hauntings Tours on Thursdays, Fridays, and Saturdays at 7:30 pm. Our spirited guide will lead you through the dark alleys, spooky side streets, and lesser-known haunted sites of the old and creaky town of Annapolis. Hear from real diary entries and newspaper […]