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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 […]

  • 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

  • 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