• Kent Island Day

    408 Love Point Rd 408 Love Point Rd, Stevensville, United States

    Each year, on the third Saturday of May, Kent Island Day commemorates the founding of Kent Island in 1631 with a parade down Main Street, historic exhibits, displays, musical entertainment, …

  • Dinner Under the Stars

    Dinner Under the Stars
    53 West Street 53 West Street, Annapolis, United States

    Don't miss Dinner Under the Stars! Enjoy cafe dining from fabulous restaurants, live music, and dancing in the street every Wednesday evening from 5:00 pm - 10:00 pm starting May …

  • Memorial Day @ Federal House

    Federal House Bar & Grille, 22 Market Space, Annapolis, MD 21401, USA

    Come celebrate the long weekend with us on May 25, 2026 from 11:00 am to 12:00 am at Federal House!

  • Annapolis Irish Festival

    Annapolis Irish Festival
    Anne Arundel County Fairgrounds 1450 Generals Highway, Crownsville, United States

    The Annapolis Irish Festival roars back in 2026 with your beloved Irish bands and a lot of craic! Enjoy Carbon Leaf, Gaelic Storm, Scythian, Dublin 5, and more! This Irish celebration goes Friday night and all day Saturday! Join us Friday night for our first responder and military night featuring two incredible bands. Then return Saturday for a full day of Irish fun for all ages. Enjoy great live music, delicious food and drinks, and exciting Irish-themed vendors and activities. Get …

  • Paca Girlfriends Party

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

    Wander the picturesque William Paca Garden as you enjoy a glass of bubbly and indulge in culinary creations prepared by the area’s premier chefs. Shop in our festive marketplace, meet …

    $150 – $500