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  • “Siren Songs: Ghost Stories of the Chesapeake”

    AUDITIONS “Siren Songs: Ghost Stories of the Chesapeake”
    Woods Memorial Presbyterian Church 611 Baltimore Annapolis Blvd, Severna Park, Maryland

    Siren Theatre Collective is seeking volunteer performers for our autumnal staged reading, "Siren’s Song: Ghost Stories of the Chesapeake." Join us for an evening of haunting tales, local legends, and mysterious stories inspired by the Chesapeake region's rich folklore. www.sirentheatrecollective.org/volunteers/auditions Stories compiled and staged by Robin Schwartz. Performances Thursday, October 29 & Friday, October 30 […]

  • The Pirates of Penzance

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    Duty, love, and laughter set sail in this swashbuckling comedy! The Pirates of Penzance is a delightful adventure filled with romance, mischief, and mistaken identity! Young Frederic believes his years of apprenticeship under a band of pirates is finally over when he falls for Mabel, daughter of the Major-General. But an unexpected twist threatens both his […]

    $28 – $120

  • CP presents The Legend of Sleepy Hollow

    CP presents The Legend of Sleepy Hollow
    The Colonial Players of Annapolis 108 East Street, Annapolis, Maryland

    Written by John Heimbuch and Jon Ferguson Directed by Alex Brady Some stories are told. Some stories are witnessed. Washington Irving’s classic ghost story gallops to life in this inventive adaptation full of humor, suspense, and autumnal magic. Follow Ichabod Crane into the misty woods of Sleepy Hollow, where every creak, shadow, and hoofbeat may […]

    $26

  • Halloween Pop-up Introductory Level Tap Routine w/ Lisa Pellittiere

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    Saturday, October 31, 2026, 9:00am-10:00am, Room 101, Price: $20.70 (TFA26LPT08) Warm-up to songs from a range of genres and learn a Halloween themed routine! Choreography will be geared towards absolute and gentle beginner teen/adult dancers (ages 14+). Check-out our other sessions! Offered about once per month September-December. A different routine is featured at each pop-up. […]

    $20.70

  • Halloween Pop-up Mixed Level Tap Routine w/ Lisa Pellittiere

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    Saturday, October 31, 2026, 10:15am-11:30am, Room 101, Price: $25.85 (TFA26LPT09) Warm-up to songs from a range of genres and leave with a Halloween routine to show off! Choreography will be geared towards advanced beginner and intermediate teen/adult dancers, but all experience levels ages 14+ are welcome! Check-out our other sessions! Offered about once per month […]

    $25.85

  • Tavern Talk: Inside Annapolis’s Revolutionary-Era Taverns

    Hogshead Trades Museum 43 Pinkney St, Annapolis, MD, United States

    Stop by Hogshead Trades Museum and explore tavern life in the busy port city of Annapolis during the Revolution. Join living historian Jacob Kirsch to discover how taverns served as more than places for food, drink, and lodging—they were gathering places for news, conversation, and community. Celebrate autumn with a sip of seasonal cider, observe […]

    $5

  • Day of the Dead

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    Celebrate Culture, Community, and Tradition! The Day of the Dead Festival (Día de los Muertos) is an annual Annapolis' celebration with live music, traditional dance, altars, art, food, and family-friendly activities. Join us as we honor the heritage and traditions that bring our community together.This is a free family event but your donations are always […]

  • Día de los Muertos Festival at Maryland Hall

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    2026 Day of the Dead Festival Date: Saturday, October 31, 2026 Time: 3:00 PM – 8:00 PM Location: Maryland Hall (Annapolis, MD) Celebrate culture, community, and tradition! The Day of the Dead Festival (Día de los Muertos) is an annual Annapolis’ celebration with live music, traditional dance, altars, art, food, and family-friendly activities. Join us […]

    Free

  • Motown Concert- Dinner Under the Stars

    Dinner Under the Stars West St and Calvert St, Annapolis, United States

    Motown Concert on Saturday, October 31, 5- 9 p.m. Dinner Under the Stars About the event 🎶 FREE MOTOWN CONCERT IN ANNAPOLIS! 🎶 Spice and Motown Magic are back! Join us for an evening of classic Motown favorites on Saturday, October 31st, from 6:00 PM to 9:00 PM on the first block of West Street […]

  • That 70’s Halloween Jam

    Log Rhythm Media, 1801 West St #100, Annapolis, MD 21401, USA 1801 West Street Suite 100, Annapolis

    A Party for the Grownups! Fundraiser for Chesapeake Children's Museum Dress in your best 70's or Halloween costume! PRICE DROP $20 Proceeds go to The Chesapeake Children's Museum

    $20

  • CP presents The Legend of Sleepy Hollow

    CP presents The Legend of Sleepy Hollow
    The Colonial Players of Annapolis 108 East Street, Annapolis, Maryland

    Written by John Heimbuch and Jon Ferguson Directed by Alex Brady Some stories are told. Some stories are witnessed. Washington Irving’s classic ghost story gallops to life in this inventive adaptation full of humor, suspense, and autumnal magic. Follow Ichabod Crane into the misty woods of Sleepy Hollow, where every creak, shadow, and hoofbeat may […]

    $26

  • Honoring Maryland’s Emancipation Day at the Museum of Historic Annapolis

    Honoring Maryland’s Emancipation Day at the Museum of Historic Annapolis
    Museum of Historic Annapolis 99 Main Street, Annapolis, MD, United States

    On November 1, 1864, a new state constitution abolished slavery in Maryland. Join us at the Museum of Historic Annapolis as we recognize and honor this historic event with a day of special programming and engaging activities- all included with Museum admission. 45-minute guided museum tours spotlight African American history, celebrate Maryland’s Emancipation Day, and […]

    $7

  • First Sunday Arts Festival

    First Sunday Arts Festival
    Annapolis, 60 West St, 60 West Street, Annapolia, Maryland

    First Sunday Arts Festivals - Where Community and Arts FuseA monthly (May to November) street festival on the first Sunday of the month featuring 130 local and regional artisans, live music and café dining.  

    FREE

  • Honoring Maryland’s Emancipation Day at the Museum of Historic Annapolis

    Honoring Maryland’s Emancipation Day at the Museum of Historic Annapolis
    Museum of Historic Annapolis 99 Main Street, Annapolis, MD, United States

    On November 1, 1864, a new state constitution abolished slavery in Maryland. Join us at the Museum of Historic Annapolis as we recognize and honor this historic event with a day of special programming and engaging activities- all included with Museum admission. 45-minute guided museum tours spotlight African American history, celebrate Maryland’s Emancipation Day, and […]

    $7

  • Paint From Your Soul Class

    AND Creative Gallery 1851 McGuckian Street, Suite B, Annapolis, MD, United States

    Join us for a special 3-hour class, Paint From Your Soul, featuring "The Healer" archetype. This transformational art experience helps women step away from daily stress, nurture themselves, and focus on healing their souls through creative expression. In this intimate, heart-centered session, we will explore the energy of The Healer to foster deep self-compassion, emotional […]

    $85

  • The Letting Go Tree

    Chesapeake Children's Museum 25 Silopanna Rd, Annapolis, Maryland

    It's time to let go! of grievances, of grief, of regrets, of remorse - the negative energy that keeps us from fully moving forward. Artist /poet Crystal Lynch leads a workshop about letting go culminating in creating our individual "leaves" to hang on a tree in the park.

    Free

  • The Pirates of Penzance

    Maryland Hall 801 Chase St., Annapolis, MD, United States

    Duty, love, and laughter set sail in this swashbuckling comedy! The Pirates of Penzance is a delightful adventure filled with romance, mischief, and mistaken identity! Young Frederic believes his years of apprenticeship under a band of pirates is finally over when he falls for Mabel, daughter of the Major-General. But an unexpected twist threatens both his […]

    $28 – $120

  • CP presents The Legend of Sleepy Hollow

    CP presents The Legend of Sleepy Hollow
    The Colonial Players of Annapolis 108 East Street, Annapolis, Maryland

    Written by John Heimbuch and Jon Ferguson Directed by Alex Brady Some stories are told. Some stories are witnessed. Washington Irving’s classic ghost story gallops to life in this inventive adaptation full of humor, suspense, and autumnal magic. Follow Ichabod Crane into the misty woods of Sleepy Hollow, where every creak, shadow, and hoofbeat may […]

    $26