Annapolis Powerboat Show
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
Events
October 2026
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Autumn Reggae Wine & Music Festival
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
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HoCo Pride
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
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Georgetown Canal Day
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
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Roktoberfest
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
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Fiesta Baltimore 2026
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
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The Ramble Festival
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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Bowie Fall Fest
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
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PRIDE Southern Maryland
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
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Featured: Dan Haas
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…
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Fantastic Negrito Quartet
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,…
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Healing Bags with Vintage Fabrics Workshop
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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Oyster Stroll
Locust Lane East Main Street 43, Westminster, Maryland 21157, United States
Shop, slurp, and stroll through Downtown Westminster! This annual festival features oysters, music, food and fun for the community and is designed to raise awareness about Chesapeake Bay farm-raised oysters.…
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Holy Trinity Heritage Festival
Holy Trinity Russian Orthodox Church 1723 East Fairmount Avenue, Baltimore, MD 21231, United States
Come enjoy a full weekend of delicious, authentic foods prepared for you by our church parishioners. We will serve our traditional beef stroganoff, shashlik, pelmeni, blinchiki, and many of our…
Free
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Oktoberfest – Gaithersburg
Kentlands Mansion 320 Kent Square Rd, Gaithersburg, MD
Dust off your dirndl, grab your lederhosen and get ready to Prost! The festival takes place in and around the Arts Barn, Kentlands Mansion, Kentlands Village Green and along Main Street…
Free
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FALL HARVEST FESTIVAL AND WAR OF 1812
Hancock’s Resolution 2795 Bayside Beach Road, Pasadena
Fall festival and War of 1812 remembrance. Music by the Overtones – Build A Scarecrow – Make A Corn husk doll – Grind Corn into Meal – Milk a wooden…
Free
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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
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Baltimore Taco Festival
Power Plant Live! 34 Market Place, Baltimore, Maryland
Taco Heaven returns to Baltimore for Maryland’s BIGGEST taco festival in history! We are shutting down the entire city block and filling it with over 30 of the area’s most…
$9.98 – $62.99
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Navy Women’s Volleyball vs Lehigh
Wesley A. Brown Field House United States Naval Academy, Annapolis, United States
Don’t miss this Navy vs Lehigh women’s volleyball game on October 11, 2026 at 3:00 pm. This event will take place at the Wesley A. Brown Field House. (DNML)
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COSMIC Symphony Presents “The British Are Coming”
Nancy R. and Norton T. Dodge Performing Arts Center 47855 College Drive, St. Mary's City, 20686, United States
Join us for an exciting opening to our 2026-2027 season with “The British are Coming,” featuring solo tubist Jasmine Pigott! This concert features works of Walton, Elgar, and Vaughn Williams.…
Free
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