• Naptown Flea w/ Annapolis Idiot

    Maryland Hall 801 Chase Street, Annapolis, Maryland, United States

    In collaboration with Naptown Vinyl & Vintage and Maryland Hall, Naptown Flea goes indoors for the first time! Come dig, shop, vibe, and kick off the season with the best …

  • Naptown Flea Vintage & Vinyl Market

    Maryland Hall 801 Chase Street, Annapolis, Maryland, United States

    Naptown Flea Vintage & Vinyl! Come join us at 801 Chase St on February 1, 2026 at 11:00 AM (Eastern Time) for a day filled with amazing vintage finds and …

    Free
  • Maryland’s Best Expo 2026

    Navy-Marine Corps Memorial Stadium 550 Taylor Ave, Annapolis, United States

    The only expo like it in the state, this event is an opportunity for Maryland farmers, seafood producers, and processors to connect with buyers. Over the past two decades, MDA’s Marketing Program, …

  • Maryland Sheep & Wool Festival

    Maryland Sheep & Wool Festival

    Howard County Fairgrounds 2210 Fairgrounds Rd, West Friendship, United States

    The Maryland Sheep & Wool Festival is one of the largest festivals of its kind celebrating all things sheep, from hoof to handwoven. The Maryland Sheep & Wool Festival will …

  • Day on the Bay to St. Michaels

    Day on the Bay to St. Michaels

    1 Prince George Street 1 Prince George Street, Annapolis, United States

    Cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore. Enjoy one complimentary non-alcoholic beverage on the way there! This quaint historic village offers fresh seafood, boutique shopping, …

    $45 – $118