Oktoberfest – Oct. 11 & 12


The annual Old Town Winchester Oktoberfest presented by Compass West Realty returns on October 11-12. Attendees will have the opportunity to enjoy German inspired beer and food while experiencing sights, sounds and traditions of Oktoberfest. This event happens throughout Old Town Winchester, including the Loudoun Street Mall, historic Taylor Pavilion and the 1840 Courthouse lawn.

NEW THIS YEAR: Keg tapping ceremony with Austrian horses!  The public is invited to join Austrian Haflinger horses, Yeager and Meister, in a procession beginning near cork and Loudoun on the Old Town Walking Mall Friday October 11th at 7:30 pm. Organ grinder, Lola, Yeager and Meister will deliver authentic German hackerphsorr-marzin beer to ticket holders for a free tasting at the Historic Taylor Pavilion.

NEW THIS YEAR: Our first ever Bürgermeister crowning!  Winchester’s first Bürgermeister will preside over this year’s event and “oversee the necessary cohesion for the good of Old Town’s Oktoberfest”.  Announcement and official swearing in ceremony on September 20th on the Civil war Courthouse steps.

Entertainment is free to all attendees, not just ticket holders. Guests that choose to purchase a ticket will receive six tastings (for beer or wine) and a commemorative glass beer stein.  Alcohol sales are limited to ticket holders.  Tickets are $20 until midnight October 10 and $25 October 11 and 12 (event days).  Tickets are good for one day only.  Guests who have purchased a ticket can also purchase additional tastings or a full drink for $5 during the event.

The Continentals, A high-energy Oktoberfest band will be returning to the Historic Taylor Pavilion this year on Friday & Saturday! This band has a wide repertoire specializing in fun upbeat Oktoberfest traditional tunes and fun traditions. Also featured on Saturday is over 30 members of Alt Washingtonian Schuhplattler Verein, the “Original Bavarian Dance Club of Washington, D.C.”, in authentic German costume.

Old Town Winchester will celebrate our German heritage with traditional beverages, accordionists, dancing, stein holding contests, a costume contest (Saturday) and Bavarian inspired food. Get your tickets now at EnjoyOTW.com or one of the ticket outlets: Total Image & Workingman’s Store, Espresso Bar & Café, Compass West Realty, Apple Federal Credit Union and the Winchester-Frederick County Convention & Visitors Bureau.

WHEN: Friday, October 11 – Saturday, October 12

TIME: Friday 5 – 11 p.m., Saturday Noon – 8 p.m.

WHERE: Old Town Winchester Loudoun Street Mall, Historic Taylor Pavilion and Courthouse Lawn

COST: $20 Advance Tasting Package, $25 Day-of Tasting Package

Ticket Details: 

  • Our online advance tasting package is just $20, which includes six tastings and a 12oz glass beer stein.
  • Tasting packages, the day of the event, are $25 and include the six tastings and stein as well.
  • General admission is FREE! If you just want to relax in the wonderful German atmosphere, feel free to bring anyone down and partake in the German culture.

Click here for Tickets to Oktoberfest

Interested in volunteering at Oktoberfest? Click here to learn more information!

Winchester offers many great hotels and lodging options to choose from to accommodate out of town guests! Check out this list of lodging options in the area! (Button for the below link)
Hotels & Accomodations

Presenting SponsorCompass-West-Realty-Banner-Logo

Featured Sponsor

Integrity Homes Cropped


Event Sponsors

Apple FCU
Shenandoah Valley Orthodontics
Compass West Realty
Bath Fitter
RBC Wealth Management
Lee Graff
Bold Rock Hard Cider
Renewal By Anderson
Ridgerunner Container Services
Virginia Eagle Distributing
KEE Construction
Q102 Shenandoah Country
Signet Screen Printing & Embroidery
92.5 WINC FM
Grand Rental Station
99.3 FM The Fox
Dr. Robert Bowen
News Talk 1400
Paulaner Beer
Devil’s Backbone Brewery
KISS 98.3
Winchester Aquarium
Integrity Staffing Services
Prime Lending

Friends of Old Town Winchester Sponsors:

TWG Insurance
United Capital
RBC Wealth Management
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