This Weekend in Door County: A Speakeasy, AutumnFest & Oktoberfest

AutumnFest in Baileys Harbor

Baileys Harbor’s AutumnFest welcomes the start of fall this weekend with a variety of fun events that seek to offer something for everyone. From a speakeasy casino party to a classic car show, farmers’ market and 5K running event, partake in one activity or do them all for a fun-filled weekend on the lake side!

Friday Night: Speakeasy Casino Night

Maxwelton Braes, Thyme Cuisine and the Ellie Helm Foundation will host the second annual Speakeasy Casino Night – casino events, blackjack, craps, poker and roulette for a good cause – on Sept. 27 in the lodge hall. 

Saturday Morning: Hey Hey 5K

The 5th annual Hey Hey 5K run starts at Door County Brewing Co. Taproom & Music Hall. Runners can register Sept. 27, 6-9 pm; or Sept. 28, 7-7:30 am, at the brewery.

Saturday: AutumnFest and Pin Ups & Pistons Auto Show

Oktoberfest at Hügel Haus

This year, in addition to the longtime fall celebrations, we’ll see the start of a new tradition at the Hügel Haus in Ellison Bay, where an official Oktoberfest celebration will take place Sept. 28. 

The celebration will begin at 9 am with yard games, an outdoor party tent, beer trailer, friendly games of hammerschlagen (pounding nails into a log) and food specials including pretzels, Door County Custom Meats bratwurst, sweet-mustard pulled pork and more. 

Shopping, Art & Community

Sturgeon Bay’s Homecoming

Also on Friday, catch a parade through downtown Sturgeon Bay (4pm) in honor of the High School’s Homecoming celebration. Tailgate party outside Memorial Field (5pm). Bonfire (6pm). Football game vs. Algoma (7pm).

Inside / Outside Sale in Fish Creek

Fish Creek retailers will showcase special sale merchandise both inside and outside of their shops for unbeatable end-of-season sales all weekend long. For those not so fond of walking; free trolley rides will be offered throughout the village on Saturday. Look for the Trolley stop signs to be able to hop on. Visit for more information.

PortSide Open Houses

Two newly-designed and constructed homes and two remodeled homes are featured. PortSide’s consultants will be on hand to answer any questions and discuss home design, construction or remodel projects. Free and open to the public. No tickets needed. For directions, visit and click on “PortSide Builders 2019 Door County Open House Tour.”

Challenge Walk MS in Egg Harbor

This 3-day, 50-mile (30-mile option available) experience will test your strength and spirit in addition to making an extraordinary difference in the lives of people with multiple sclerosis. Visit for more information and to register.

Art & Galleries

There is a Fall Art Fair and Veg Fest at the Settlement Shops in Fish Creek, an artist reception for “Art Show 6: From the Land” at Plum Bottom Road Gallery, an artist demo and reception for Cynthia Koshalek at Artzy Studio in Ephraim, and an opening reception featuring the work of Monica Ramirez, a Sturgeon Bay artist and founder of Mona Lucy’s Art, at Hope Church Art Alcoves Gallery.

Live Music

Wade Fernandez and Bill Miller, Contemporary Native Americana artists, are performing at the Door Community Auditorium. The Nightinjails, two established female artists, are combining acoustic guitar, violin, and vocals at Fiddler’s Green. And Upstate, an Americana sextet that offers luscious three-part harmonies to a mix of genres and sounds that include folk, rock, swing, jazz, R&B and a whole lotta gospel soul, will be at Door County Brewing Co. to close out Saturday’s AutumnFest festivities.

But of course, there is a lot more music happening too, take a look at the Live Music Calendar to plan your weekend.

For the full calendar of all the happenings, click here!