RocktoberFest
Whalen Commons 19701 Fisher Avenue, Poolesville
Annual Fall Festival featuring live music, local breweries, and plenty of kids activities!
Free
Events
October 2026
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Featured: Mike Heuer
Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States
Mark your calendars for this weekend at the Beer Farm, where Mike Heuer will take the stage with his unique blend of Alt/Folk-Pop! With 14 years of experience as a…
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SpookyFest
Bayhead Park 1661 Bay Head Rd, Annapolis
SpookyFest brings back your absolute favorite traditions alongside brand-new, upgraded experiences the whole crew will love. Your favorite Fall Festival classics—like the Haunted House, Halloween movies in the theatre, and…
$11 – $27
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Haunted Hike and Trick or Treat Trail
New Germany State Park 349 Headquarters Lane, Grantsville
Celebrate the season by completing the Trick-or-Treat Trail for kids age 12 and under, or a Haunted Hike spooky adventure. Trick or Treat Trail for ages 12 and under. 5-6:30 p.m.…
Free
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English Dance to delightful live music, excellent callers and friendly community
Dance like it’s 1776 to lovely live music as was done throughout the American colonies, including right here in Annapolis. Dances are held the 3rd Saturday of each month at…
$5 – $15
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English Dance to delightful live music, excellent callers and friendly community
Annapolis Friends Meetinghouse 351 Duboise Rd., Annapolis, 21401, United States
Dance like it’s 1776 to lovely live music as was done throughout the American colonies, including right here in Annapolis. Dances are held the 3rd Saturday of each month at…
$5 – $15
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Annapolis Sailboat Show
Annapolis City Dock Dock Street, Annapolis, Maryland 21401
Walk the floating docks during the Annapolis Sailboat Show, climb aboard gleaming yachts and center consoles, and explore everything from family cruisers to weekend fishing rigs. Whether you’re boat-curious, shopping…
$10 – $32
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Art @ the Park 2026
Quiet Waters Park 600 Quiet Waters Park Road, Annapolis, Maryland 21403
Enjoy live music, an outstanding display of art, including ceramics, woodworking, jewelry, and painting, along with demonstrations and a variety of food trucks. There will be art activities for young…
$8
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Maryland Avenue Fall Festival
Maryland Avenue Annapolis Maryland Ave and State Circle, Annapolis, Maryland 21401
Entertainment, food, demonstrations and shopping along Maryland Avenue.
Free
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U.S. National Oyster Festival
St. Mary’s County Fairgrounds 42455 Fairgrounds Road, Leonardtown
US National Oyster Shucking Championship, Tasting Tent, Stories from a Mermaid, educational exhibits, live performances.
$50
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Frederick Fall Festival
Carroll Creek Linear Park Frederick
Join us for a day of family fun and community spirit! Live Music, Handmade Goods & Local Art. Delicious Food, Treats & More Free Kids’ Activities like twisted balloons and…
Free
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Featured: One Night Only Band
Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States
One Night Only Band brings a high-energy mix of rock, classic rock, country, and alternative favorites to the Beer Farm. Based in Annapolis, this five-piece group puts its own spin…
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2026 Walk to End Alzheimer’s – Annapolis, MD (Anne Arundel)
Sandy Point State Park 1100 East College Parkway, Annapolis, MD 21401, United States
Join our Interim HealthCare of Annapolis team as we Walk to End Alzheimer’s. Come together for an inspiring community event that celebrates our commitment to ending the disease. Join us…
Free
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Maryland Concert Series Presents…Groove Spot Band & Show
Chesapeake Arts Center 194 Hammonds Lane, Brooklyn Park, 21225, United States
Maryland Concert Series Presents… Groove Spot Band & Show Sunday, October 18, 2026 Hammonds Lane Theatre 3PM $15-$30 I ( $1.45-$1.90 fees)
$1.45 – $30
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Featured: Anthony Frijia
Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States
Join us for an afternoon of incredible music with Anthony Frijia! Hailing from the rolling hills of Maryland, Anthony’s “Nomadic Americana” sound blends lyrically-driven folk, blues, and country, captivating audiences…
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Busch Annapolis Library Fall Film Series: Alfred Hitchcock – Master of Suspense
Busch Annapolis Library 1410 West Street, Annapolis, Maryland 21401
This month we’ll delve deeper into the rich catalog of films directed by the great Alfred Hitchcock. Each movie is introduced by area cinephile Ann Glenn with info about the…
Free
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Social Security – Understanding the Ins and Outs of Social Security
Zoom
Get information you need about Social Security—from when to claim benefits to understanding spousal options and retirement age. This comprehensive webinar answers your questions and provides the knowledge to help…
Free
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First Exposure: Beginner Photography (4- week workshop)
ArtFarm Annapolis 111 Chinquapin Round Road (suite 200), Annapolis, MD 21401, United States
Have a digital camera but don’t know how to use it? Want to brush up on your photography skills? Join photographer Kaitlyn McQuaid for “First Exposure,” a 4-week digital photography…
$225
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Featured: CA$H BA$H
Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States
Join the Junior League of Annapolis, Inc. (JLA) for our 2026 CA$H BA$H fundraising event at the Beer Farm at Homestead Gardens! CA$H BA$H brings a fun reverse raffle, live…
$50
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Featured: Mahjong 101 | Beginner Class – The Gardens
The Gardens 743 W Central Ave, Davidsonville, MD 21035, United States
Always wanted to learn American Mahjong? Mahjong 101 is a fun, approachable introduction for complete beginners, giving you the foundation you need to understand the game without feeling overwhelmed.
$50
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