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  • Watermarks Kids Halloween Costume Cruises

    Cruises on the Bay by Watermark 1 Dock Street, Annapolis, Maryland

    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 […]

  • MD Concert Series Presents…Big Buffett Beach Band

    Chesapeake Arts Center 194 Hammonds Ln, Brooklyn Park, MD, United States

    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, […]

  • Spirits of the Past: Disease, Death, and Mourning Tours

    William Paca House and Garden 186 Prince George Street, Annapolis, MD, United States

    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 […]

  • Jane Austen Tour and Book Club

    Hammond-Harwood House 19 Maryland Ave, Annapolis, MD, United States

    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 […]

  • Orlando Ridout V Memorial Lecture

    Governor Calvert House 58 State Circle, Annapolis, MD

    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 […]

  • Special Tour: Dark History of the South River

    Historic London Town and Gardens 839 Londontown Road, Edgewater, MD, United States

    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 […]

    $12

  • Special Historic Hauntings with Watermark Tours

    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 […]

  • Wilma Lee Halloween Cruise

    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 […]

    $85

  • Special Historic Hauntings with Watermark Tours

    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 […]

  • Brewer Hill Cemetery Tour with Historic Annapolis

    Join us for a guided walking tour of Brewer Hill Cemetery in honor of Emancipation Day.   Maryland Emancipation Day is observed on November 1st to commemorate the abolition of […]

  • Discovering American Art: Silver in the Golden Age of Annapolis

    Hammond-Harwood House 19 Maryland Ave, Annapolis, MD, United States

    This year the annual Discovering American Art lecture series focuses on silver and the artisans who produced elegant but useful pieces in early Annapolis. Annapolis was a thriving colony in […]