Oktoberfest is what Annapolis does with a free weekend. The beer gardens take the loud nights with live music, giant steins and dancing, and lederhosen stay optional. The communal tables carry the quieter ones, bratwurst and pretzels arriving steadily, the German food better than it has to be. Or a good beer with friends, nothing after. Browse Oktoberfest 2026 events and parties across Annapolis, check the dates and venues, and book your tickets while there's still room.
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Sat, Oct 24970 St. John’s Drive
🎉 Saint John’s 18th Annual Block Party — Oktoberfest Celebration! 🍂🎶 Saturday, October 24th | 12 PM–10 PM 📍 Saint John’s Drive — Annapolis, MD between Summit and Latrobe Drive 🎶 LIVE MUSIC ALL DAY We’ve got an awesome lineup keeping the party going
Live music
Get the look
Outfits, steins and party kit for the season. Check delivery dates before you order.
Links go to Amazon. As an Amazon Associate, AllEvents earns from qualifying purchases.
Dirndl dressBodice, blouse, skirt and apronShop on Amazon 
Men's lederhosenLeather shorts, braces and allShop on Amazon 
Alpine hatGreen felt, with the featherShop on Amazon 
Trachten suspendersThe look for less, over any checked shirtShop on Amazon 
Lidded beer steinCeramic, with a pewter lidShop on Amazon 
Das Boot glassThe boot-shaped party glassShop on Amazon 
Hammerschlagen gameA stump, nails, a hammer: first nail flush winsShop on Amazon 
Bavarian flagBlue-and-white diamonds for the yardShop on Amazon 
Pretzel saltCoarse salt for homemade BreznShop on Amazon 
Baby lederhosenFor the smallest guestShop on Amazon 
Hot-dog dog costumeFor the dachshund racesShop on Amazon Nearby
Worth the trip from Annapolis, soonest first.
Oct 2–4Saint Katherine Greek Orthodox Church, Hall Rental, Falls Church3 days
Free
Sat, Oct 3District Pier at The Wharf, Washington
$33.85 – $39.19
Sat, Oct 3The Wharf, Washington
Sat, Oct 3Frederick Fairgrounds - Home of The Great Frederick Fair, 797 E Patrick St, Frederick, MD 21701, USA
Sat, Oct 10Maryland State Fairgrounds, Lutherville-Timonium
$59.76 – $97.07Live music
Sun, Oct 11Kentlands Blvd, Gaithersburg, MD 20878, United States
Oct 16–17St. Mary's College of Maryland Admissions Building, Saint Marys City2 days
Free – $55.20Live music
Asked and answered
Oktoberfest events in Annapolis run from Oct 24 to Oct 24, 2026: 1 event.
Nothing is listed in Annapolis itself for Oct 2 – Oct 4, but 5 events are on nearby, in Falls Church, Washington and Frederick.
Yes: 9 more events are listed within reach of Annapolis, in Falls Church, Washington, Frederick and Lutherville-Timonium and more. The soonest is Saint Katherine's Greek Festival October 2026(Falls Church, VA) in Falls Church, on Oct 2–4.
Munich's Oktoberfest runs from September 19 to October 4, 2026, 16 days on the Theresienwiese. It is on now: today is day 13.
Worth the trip
Where the season is the whole city's business, from Munich's meadow to a Bavarian village in the Cascades.
MunichThe original, since 1810
CincinnatiOktoberfest Zinzinnati
KitchenerCanada's biggest
La Crosse, WIOktoberfest USA
Frankenmuth, MIMichigan's Little Bavaria
Leavenworth, WAA Bavarian mountain village
Fredericksburg, TXHill Country's German town
New Ulm, MNSettled by Germans in 1854
DenverDenver Oktoberfest, since 1969
MilwaukeeBrew City's German roots
ChicagoStreet fests all season
New YorkStone Street and the beer hallsKeep exploring
