Guide to Oktoberfest in the City 2026

Get your lederhosen and beer steins ready! This October, Boston has fun festivals and unique beers galore!
Oktoberfest at the Anchor in Charlestown with a Tartan Twist
Harpoon Oktoberfest
Boston’s classic fest features live oompah music, chicken dancing, and stein hoisting. Friday night features “Glowtoberfest” (black-light party) and Saturday is the classic festival. October 2–3, 2026. Tickets start at $15. Tickets here!
Oktoberfest at Dorchester Brewing
Saturday, October 3rd, Dorchester Brewing Company is hosting Oktoberfest. They’ll have beer, cocktails, live music, food, and a stein-holding competition! More info here!
The Tall Ship Oktoberfest
October 3, 2026, starting at 1:00 PM. The 6th annual event features over 40 local craft beers, German food specials, and live music by Kier Byrnes & The Kettle Burners. Tickets here!
Time Out Market “Munich at the Market”
October 3, 1-5PM. An afternoon celebration with German beers, Bavarian bites, and themed games. Tickets here!
Club Volo Oktoberfest
Celebrate Oktoberfest, October 10th, with games, beer, and good vibes at Club Volo at Assembly Row. Play pickleball, volleyball, cornhole, Connect 4, and Jenga, test your strength in stein-holding competitions, enjoy the on-site bar, and snag exclusive giveaways from partners and vendors. More info and tickets here!
Castle Island Brewing Oktoberfest
October 17, 2026, starting at 11:00 AM. Features local brews, food pairings, and live music from Kier Byrnes & The Kettle Burners. Tickets here!
Check back as this list may be updated!
Maureen Dahill is the editor of Caught in Southie and a lifelong resident of South Boston sometimes mistaken for a yuppie. Co-host of Caught Up, storyteller, lover of red wine and binge watching TV series. Mrs. Peter G. Follow her @MaureenCaught.

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