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…
Maryland Hall 801 Chase Street, Annapolis, Maryland 21401, United States
Fall Classics: A Concert for Peace Saturday, October 10, 2026 – 7:30 pm MD Hall for the Creative Arts Repertoire: Karl Jenkins – The Armed Man: A Mass for…
Rams Head On Stage, 33 West St, Annapolis, MD 21401, USA West Street 33, Annapolis, Maryland 21401, United States
A mix of elegance and function, this 10-piece band pays its homage to the recent touring versions of Steely Dan. Technicolor Motor Home will perform at Rams Head On Stage.…
$33 – $61
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
Thurmont Main Street Center 11 Water Street, Thurmont
Local art, jewelry, crafts, and a variety of delicious food are just a few of the fun things you will find at this annual event! Amazing crafts, art, jewelry, clothing,…
Free
Annapolis City Dock Dock Street, Annapolis, Maryland 21401
October brings the transformation of Ego Alley and Annapolis Harbor into a boater’s dream, as floating docks create a temporary marina showcasing new and premiering boats and the latest in…
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…
Chesapeake Bay Environmental Center 600 Discovery Ln, Grasonville, United States
Don’t miss the CBEC Fall Fest! There will be oysters, live music, sunset sound healing, Halloween bingo, an adult yoga soul flow, and children’s yoga. Register here! This event will…
Annapolis City Dock Dock Street, Annapolis, Maryland 21401
Annapolis Powerboat Show, Oct 8–11. Boats, food, and waterfront fun for the whole family — no boating experience required.
$10 – $32
Linganore Winecellars 13601 Glissans Mill Rd., Mt. Airy
Cool reggae vibes paired perfectly with your favorite Maryland wines for a fall afternoon unlike any other.
$40.27 – $106.13
Merriweather Post Pavilion 10475 Little Patuxent Parkway, Columbia
Join us for a vibrant day of community, connection, inclusion, and pride. Whether you’re attending with friends and family, showcasing your organization, supporting the event as a sponsor, or volunteering…
Free
Mule Yard and Canal Boat Thomas Jefferson Street Northwest, Washington, District of Columbia 20007, United States
Georgetown Heritage is once again celebrating our beloved C&O Canal with a free day of festivities in the Mule Yard and onboard the canal boat. The family-friendly event is free…
Free
Guinness Open Gate Brewery 5001 Washington Blvd, Halethorpe
Enjoy live rock music under our Munich-inspired tent all weekend long, plus exclusive Oktoberfest beers and Bavarian-inspired food specials. We’re keeping Oktoberfest rocking and rolling!
Free
Patterson Park 2801 Eastern Ave, Baltimore, Maryland
Fiesta Baltimore is the largest and most anticipated Latino cultural event in the Baltimore metropolitan region. The event brings together families, artists, musicians, performers, and community leaders from across the…
Free
Camp Ramblewood 2564 Silver Road, Darlington
The Ramble Festival is a three-day vibe-centric music festival focused on good people sharing great music and creating terrific times. At The Ramble, it’s all about creating community through shared…
$110 – $300
Bowie Town Center 15608 Emerald Way, Bowie
Enjoy complimentary wine tastings, live music, and a delicious variety of food. Browse unique finds from vendors and artisan exhibitors while soaking in the festive atmosphere. This event offers something for…
Free
Lexington Manor Passive Park 21675 South Coral Drive, Lexington Park
One of the best events held in Southern Maryland, every year just gets better. It’s wonderful to have an inclusive space for all people regardless of identity or expression.
Free
Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States
Get ready for an electric night of acoustic vibes with Dan Haas at the Beer Farm! Dan’s high-energy solo set blends catchy melodies, heartfelt lyrics, and a whole lot of…
Rams Head On Stage, 33 West St, Annapolis, MD 21401, USA West Street 33, Annapolis, Maryland 21401, United States
Fantastic Negrito is a powerhouse performer whose live shows are charged with emotion, intensity, and connection. Blending Delta blues, soul, funk, and rock, he delivers dynamic sets built on rhythm,…
AND Creative Studio 1851 McGuckian St Suite B, Annapolis, United States
Inspired by “All That She Carried” by Tiya Miles, this intimate fiber art workshop explores the ancestral tradition of carrying a bag—not simply for what we need, but for what…
$95
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