You don’t need a kirtle or lederhosen to celebrate the German holiday of Oktoberfest. This Bavarian tradition, which originated in Munich, came to America with German immigrants, who keep the tradition alive today. The celebration of food and drink is a fun and festive way to launch the fall harvest season. In the Annapolis area, there are several restaurants, breweries, and other businesses you can visit.
So pour yourself a lager (or a root beer) and start practicing your ‘Guten Tag’ and ‘Danke Schön’ so you can enjoy one of these Oktoberfest events.
Old Stein Inn
For an authentic, traditional German meal any time of year, head to this Edgewater establishment. They have an outdoor biergarten and Bier Bar so you can try one of their many craft beers. You can join them for German Music Sunday or catch local bands on Friday nights, depending on your music taste. And their Oktoberfest Menu will include not only the classics of currywurst and schnitzel, but also some crab and Old Bay flavors!
Where: 1143 Central Avenue East, Edgewater, MD, 21037
When: Restaurant hours: Wednesday to Thursday, 4 to 10 PM. Friday, 4 to 11 PM. Saturday, noon to 11 PM. Sunday, noon to 9 PM. Happy hour: Wednesday to Friday, 4 to 6 PM, bars only.
West Annapolis Oktoberfest
The West Annapolis Business Association, along with Chessie’s Wharf and RAR Brewing, will take over the streets with bites and brews from local food trucks and restaurants. A beer garden will give you a taste of Munich before you walk around to visit Annapolis businesses. They encourage you to use this opportunity to “kick off your holiday shopping early with unique finds from our variety of vendors.” Finish up that Christmas list with months to spare!
Where: Annapolis Street in West Annapolis
When: Sunday, September 27, 11 AM to 4 PM.
Forward Brewing
On September 26 and 27, this Eastport establishment will be ready to serve up their brews. According to their Instagram, they “will be pouring steins of our crushable Märzen-style lager, making New Roots Farm brats and kraut, playing Ein Prosit, and enjoying the first weekend of fall.”
Where: 418 Fourth Street, Annapolis, MD 21403
When: Saturday, September 26, 11 AM to 9:30 PM. Sunday, September 27, 11 AM to 8 PM.
Oktoberfest at Garten
Before you head to Garten in Severna Park, you might want to limber up. There are two events, one for grown-ups and one for kids. On September 19, kick off Oktoberfest with a stein-holding competition. The $20 entry fee includes a glass stein and beer. The winner will get their name etched on a Garten stag trophy. That same day, they will launch their Oktoberfest menu. Come hungry, because they will have a hot dog tower (think one of those afternoon tea display trays, but with hot dogs instead of finger sandwiches). And on September 26, the Oktoberfest for Kids event will include a live alpine horn demo by Alphorn Productions and a kids’ version of the stein-holding competition—this time with root beer!
Where: 849 Baltimore Annapolis Boulevard, Severna Park, MD 21146
When: Kickoff Party: Saturday, September 19, 11 AM with stein-holding competition at noon. Oktoberfest for Kids: Saturday, September 26, from 11 AM to 3 PM, with root beer stein-holding competition at noon.
This Oktoberfest, say goodbye to summer and hello to the autumn harvest season with German flair. You’ll be dancing to polka music and hoisting giant steins in true Bavarian-American fashion. The whole family will love the festivities. Be sure to say “prost” while raising a glass to Annapolis!
Eye on Annapolis: Top 5 in the News | Sept. 15, 2026 |