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
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
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
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…
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…
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…
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
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
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
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…
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 for the Creative Arts 801 Chase St, Annapolis, Maryland 21401, United States
Live Arts Maryland opens the season with music that explores peace, compassion, and our shared humanity. Karl Jenkins composed The Armed Man: A Mass for Peace as a response to…
$52 – $65
Maryland Hall 801 Chase Street, Annapolis, Maryland 21401, United States
Live Arts Maryland opens the season with music that explores peace, compassion, and our shared humanity. Karl Jenkins composed The Armed Man: A Mass for Peace. It’s a response to…
Annapolis Market House 25 Market Space, Annapolis, United States
Maryland witnessed at least twelve witch trials. The last one was held right here in Annapolis. Several women were murdered under suspicion of witchcraft, one woman was legally executed, and…
$25
Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States
The Wombmates are a Maryland-based twin duo proving that some bandmates have been making music together since before they were born. Like roommates, but earlier, these identical performers bring twice…
Navy-Marine Corps Memorial Stadium 550 Taylor Ave, Annapolis, United States
Don’t miss the Navy football vs Tulsa game on October 10, 2026 at 3:30 pm! This event will take place at the Navy-Marine Corps Memorial Stadium. (DNML)
Fairview Farm Rutland Road 2416, Davidsonville, Maryland 21035, United States
Don’t miss JessFest! Join us for a fun event packed with “All the Things” Jess Stach Beard loved in this world while raising money for those she fought with and…
Free – $15
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
Rams Head On Stage, 33 West St, Annapolis, MD 21401, USA West Street 33, Annapolis, Maryland 21401, United States
Bat out of Helloween is more than a concert—it is a powerful live experience that brings to life the music of Meat Loaf, Rocky Horror, and other spooky hits. Bat…
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
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