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  • ART @ THE PARK 2026

    Quiet Waters Park 600 Quiet Waters Park Rd, Annapolis, MD, United States

    Join Friends of Quiet Waters Park for their annual ART @ THE PARK! October 17–18, from 10 a.m. to 4 p.m Activities & Food: Enjoy live music, an outstanding display […]

  • Spookyfest @ Children’s Theatre of Annapolis

    Children's Theatre of Annapolis, 1661 Bay Head Road, Annapolis, MD 21409 1661 Bay Head Road, Annapolis, MD, United States

    CTA’s Biggest Fall Festival Ever! Are you ready for THE MOST FUN community event of the year? Children's Theatre of Annapolis (CTA) is pulling out all the stops for Spookyfest […]

  • Porchfest Annapolis

    Murray Hill Neighborhood Annapolis

    Porchfest Annapolis is being held this year in the Murray Hill neighborhood! Saturday, October 24th, from 11:00 a.m. to 3:00 p.m. (Rain date: Sunday, October 25th) Over 10 front porches […]

    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 […]

  • 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 […]

    FREE

  • Tastings & Tunes – Wine & Beer Fest on West

    Annapolis, 60 West St, 60 West Street, Annapolia, Maryland

    Join us for an unforgettable experience featuring samples from 8 local restaurants, an impressive selection of 20 domestic and international wines, refreshing craft beers, and live music, prizes and more!

    $55

  • The Annapolis Holiday Market

    The Annapolis Holiday Market
    Annapolis Mall 2002 Annapolis Mall Rd, Annapolis, MD, United States

    Annapolis Holiday Market http://www.annapolisholidaymarket.com 1040 Annapolis Mall Road, Annapolis, MD 21401 December 4-6 and December 11-13 Hours: Fri- Sat 11 am-9 pm, Sun 11 am - 7 pm Free admission […]

  • The Annapolis Holiday Market

    The Annapolis Holiday Market
    Annapolis Mall 2002 Annapolis Mall Rd, Annapolis, MD, United States

    Annapolis Holiday Market http://www.annapolisholidaymarket.com 1040 Annapolis Mall Road, Annapolis, MD 21401 December 4-6 and December 11-13 Hours: Fri- Sat 11 am-9 pm, Sun 11 am - 7 pm Free admission […]

  • Annapolis Chocolate Binge Festival

    Inner West Street Annapolis, Maryland

    About This Event A festival celebrating chocolate! The Inner West Street Association brings you the popular Annapolis Chocolate Binge Festival to downtown Annapolis for the holidays. On Sunday, December 6th […]

    $6 – $70

  • 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 […]

    FREE

  • The Annapolis Holiday Market

    The Annapolis Holiday Market
    Annapolis Mall 2002 Annapolis Mall Rd, Annapolis, MD, United States

    Annapolis Holiday Market http://www.annapolisholidaymarket.com 1040 Annapolis Mall Road, Annapolis, MD 21401 December 4-6 and December 11-13 Hours: Fri- Sat 11 am-9 pm, Sun 11 am - 7 pm Free admission […]

  • The Annapolis Holiday Market

    The Annapolis Holiday Market
    Annapolis Mall 2002 Annapolis Mall Rd, Annapolis, MD, United States

    Annapolis Holiday Market http://www.annapolisholidaymarket.com 1040 Annapolis Mall Road, Annapolis, MD 21401 December 4-6 and December 11-13 Hours: Fri- Sat 11 am-9 pm, Sun 11 am - 7 pm Free admission […]

  • The Annapolis Holiday Market

    The Annapolis Holiday Market
    Annapolis Mall 2002 Annapolis Mall Rd, Annapolis, MD, United States

    Annapolis Holiday Market http://www.annapolisholidaymarket.com 1040 Annapolis Mall Road, Annapolis, MD 21401 December 4-6 and December 11-13 Hours: Fri- Sat 11 am-9 pm, Sun 11 am - 7 pm Free admission […]

  • The Annapolis Holiday Market

    The Annapolis Holiday Market
    Annapolis Mall 2002 Annapolis Mall Rd, Annapolis, MD, United States

    Annapolis Holiday Market http://www.annapolisholidaymarket.com 1040 Annapolis Mall Road, Annapolis, MD 21401 December 4-6 and December 11-13 Hours: Fri- Sat 11 am-9 pm, Sun 11 am - 7 pm Free admission […]

  • 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 […]

    FREE

  • 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 […]

    FREE