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  • Sip, Pour and Create!

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

    This isn’t your typical paint class—it’s an experience. Guests will create their own abstract pour painting while enjoying handcrafted mocktails and a welcoming, high-vibe atmosphere. The event is beginner-friendly and […]

    $75

  • 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 […]

  • Williamsburg-Style Wreath Making Workshop

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

    Williamsburg Medallion Workshop with Maria from Beaver Creek Cottage Garden Celebrate the season with a touch of classic Southern charm! In this hands-on workshop, Maria of Beaver Creek Cottage Garden […]

    $95

  • Sketch Night 2026

    Sketch Night 2026
    ArtFarm Annapolis 111 Chinquapin Round Rd., Suite 200, Maryland

    Teens and Adults Welcome! Live figure drawing meets killer playlist. A unique life drawing experience featuring models ranging from burlesque performers to professional life models, in both costume and nude. […]

    $25 – $325

  • 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 […]

  • Christmas Wreath Workshop

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

    Christmas Holly & Rose Wreath Workshop with Maria from Beaver Creek Cottage Garden There's nothing quite like a wreath made from flowers and foliage grown with love. In this workshop, […]

    $95

  • Christmas Wreath Workshop

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

    Christmas Holly & Rose Wreath Workshop with Maria from Beaver Creek Cottage Garden There's nothing quite like a wreath made from flowers and foliage grown with love. In this workshop, […]

    $95

  • 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 […]

  • Art Bar: Create, Sip + Socialize

    Art Bar: Create, Sip + Socialize
    ArtFarm Annapolis 111 Chinquapin Round Rd., Suite 200, Maryland

    Skip the Bar, Create at Art Bar! Third Thursdays | 6-8 PM Trade your typical night out for something extraordinary. Welcome to Art Bar – where creativity meets community in […]

    $28