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October 2026

  1. Naptown Flea

    MRE Mercantile 318 6th St, Annapolis, United States

    Naptown Flea is coming to Eastport for the first time! Shop 20+ local vintage sellers, small businesses, and creators on Sunday, October 4th from 10 AM–4 PM at MRE Mercantile.…

    Free

  2. Naptown Flea

    MRE Mercantile 318 6th St, Annapolis, United States

    Naptown Flea is coming to Eastport for the first time! Shop 20+ local vintage sellers, small businesses, and creators on Sunday, October 4th from 10 AM–4 PM at MRE Mercantile.…

    Free

  3. Autumn Abundance Farm Tour

    Honey’s Harvest Farm 5801 Brooks Woods Rd, Lothian, United States

    Learn to identify delicious, nutritious wild and cultivated edible plants and graze your way through the permaculture gardens during this 60-minute farm tour. This event will take place at Honey’s…

    $8 – $25

  4. Maryland Renaissance Festival

    Maryland Renaissance Festival, 1821 Crownsville Rd, Annapolis, MD 21401, USA Crownsville Road 1821, Annapolis, Maryland 21401, United States

    The Maryland Renaissance Festival, a tradition for the entire family, begins its 50th season on August 29th and runs Saturdays and Sundays and Labor Day Monday through October 25th for nine…

  5. Anne Arundel County Lifeline 100 Bicycle Event

    Kinder Farm Park 1001 Kinder Farm Park Road, Millersville, Maryland

    Join the Anne Arundel County Department of Recreation & Parks, Anne Arundel County Police, and Bicycle Advocates for Annapolis and Anne Arundel County (BikeAAA) for the 12th Annual Lifeline 100…

  7. Lifeline 100 Bicycle Event

    Kinder Farm Park 1001 Kinder Farm Park Road, Millersville, Maryland

    The award-winning Anne Arundel County Lifeline 100 Bicycle Event is pleased to be an inclusive event offering scenic 65 and 100 mile county tours with water views and historic sites,…

  8. Comedian Anthony Rodia

    Rams Head On Stage, 33 West St, Annapolis, MD 21401, USA West Street 33, Annapolis, Maryland 21401, United States

    Anthony Rodia is an Italian-American comedian whose razor-sharp wit, relatable storytelling, and high-energy performances have made him one of the most in-demand stand-ups in the country. Blending the chaos of…

  9. Hamlet

    Classic Theatre of Maryland 1804 West Street, Suite 200, Annapolis, 21401, United States

    Experience the play that has captivated audiences for over four centuries as Classic Theatre of Maryland opens its season with Shakespeare’s greatest masterpiece. Set within the intrigue of the royal…

    $61.75 – $98.75

  10. Our Town

    The Colonial Players, 108 East St, Annapolis, MD 21401, USA East Street 108, Annapolis, Maryland 21401, United States

    Set in the small New England community of Grover’s Corners, Our Town follows the lives of the Webb and Gibbs families as they navigate love, marriage, and loss. Our Town invites us…

  11. Station 7 Terror Trail

    Davidsonville Park-and-Ride 2701 Davidsonville Road, Davidsonville, United States

    Welcome to the AVFD Station 7 Terror Trail! We are a fully volunteer-staffed fundraising event for the AVFD Station 7. Our family-friendly haunted trail has activities for everyone: The Terror…

  12. You’re a Good Man, Charlie Brown

    Live Arts Studio at Westfield Annapolis 2002 Annapolis Mall, Annapolis, 21401, United States

    Charlie Brown and the entire Peanuts gang explore life’s great questions as they play baseball, struggle with homework, sing songs, swoon over their crushes, and celebrate the joy of friendship.…

  13. Echoes of the Earth

    Maryland Hall 801 Chase Street, Annapolis, Maryland 21401, United States

    From the whispered stillness of Antonín Dvořák’s Bohemian landscapes to the searing emotional power of Jennifer Higdon’s Cello Concerto—brought vividly to life by Julian Schwarz—Echoes of the Earth invites you into a world where…

  14. Boom Ball at Prince George’s Stadium

    Prince George’s Stadium 4101 Crain Hwy, Bowie, 20716, United States

    Boom Ball is coming to Prince George’s Stadium on Saturday, October 3! Get ready to experience baseball with a whole new twist! Boom Ball brings an unforgettable baseball experience with…

  16. Swashbuckler Slugfest

    PAL Park 1025 Bay Ridge Rd, Annapolis, United States

    Grab a bat and take your swings for Annapolis PAL. The Swashbuckler Slugfest brings the whole community out to the ball field for an afternoon of baseball, food, and friendly…

    Free – $50

  17. Navy Men’s Soccer vs Colgate

    Glenn Warner Soccer Facility Naval Academy, Annapolis, MD 21402, United States

    Don’t miss this Navy men’s soccer game vs Colgate on October 3, 2026 at 3:00 pm! This event will take place at the Glenn Warner Soccer Facility. (DNML)

  18. Pippin

    The Bowie Playhouse 16500 White Marsh Pk Dr, Bowie, United States

    Heir to the Frankish throne, the young prince Pippin is in search of the secret to true happiness and fulfillment. He seeks it in the glories of the battlefield, the…

    $19 – $30

  19. Hamlet

    Classic Theatre of Maryland 1804 West Street, Suite 200, Annapolis, 21401, United States

    Experience the play that has captivated audiences for over four centuries as Classic Theatre of Maryland opens its season with Shakespeare’s greatest masterpiece. Set within the intrigue of the royal…

    $61.75 – $98.75

  20. You’re a Good Man, Charlie Brown

    Live Arts Studio at Westfield Annapolis 2002 Annapolis Mall, Annapolis, 21401, United States

    Charlie Brown and the entire Peanuts gang explore life’s great questions as they play baseball, struggle with homework, sing songs, swoon over their crushes, and celebrate the joy of friendship.…

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