• Homeschool Day at Hogshead: Colonial Kids

    Hogshead Trades Museum 43 Pinkney St, Annapolis, United States

    Have you ever wondered what life was like for families in Colonial Annapolis? Step inside the Hogshead Trades Museum, a one-of-a-kind dwelling on historic Pinkney Street, and discover what daily …

    Free – $10
  • Bedtime Book Buddies

    Paws at the Mall 2170 Annapolis Mall Rd, Annapolis, United States

    We have missed you! This October, we are delighted to host Bedtime Book Buddies nights at our brand new Paws at the Mall location. Be among the first to visit …

  • Tractor Treat

    Homestead Gardens - Davidsonville 743 W Central Avenue, Davidsonville, United States

    Homestead Gardens is excited to welcome the community back for Tractor Treat 2026, a family-friendly fall evening celebrating local agriculture, farmers, and the equipment that keeps our community growing. Local farmers, …

    $3
  • Splash Club

    Center Lane Swim School 175 Mitchells Chance Rd, Edgewater, United States

    Don't miss Splash Club! Our goal is to bring families in our community together for a fun morning of water safety, swimming, play, and connection. Ages three months to five …

    Free – $5
  • Art @ the Park

    Art @ the Park
    Quiet Waters Park, 600 Quiet Waters Park Rd, Annapolis, MD 21403, USA

    This year marks the 36th anniversary for Art @ the Park. The festival, held in Quiet Waters Park, Annapolis, Md., is an exciting outdoor event that includes visual art, live …

    $8.00
  • Monsters on Main Street

    Main Street at South River Colony Shopping Center 179 Mitchells Chance Road, Edgewater, United States

    Grab your costumes, gather your boo crew, and head to Main Street in Edgewater for Monsters on Main, our annual frightfully fun Halloween celebration for the whole family! Dress up …