As the post-Labor Day transition settles across northeastern Wisconsin, Door County is preparing to welcome the autumn season with a dynamic roster of harvest celebrations and arts programming. The mid-September calendar serves as an essential bridge for the region, drawing early autumn visitors and building community excitement prior to the major countywide festivals slated for October.
At the center of the upcoming weekend lineup is Sturgeon Bay, where community members and seasonal travelers will gather on Sept. 18 and Sept. 19 for the 26th annual Harvest Fest and Street Art Auction. Organized by Destination Sturgeon Bay, the multi-day celebration blends civic traditions, public art, classic automobiles, and seasonal culinary offerings across both the east and west districts of the city.
A signature component of the celebration is the culmination of the citywide summer art installation, known this year as "Set Sail in Sturgeon Bay." The 2026 project pays direct tribute to the rich maritime heritage that has shaped both the city and the surrounding peninsula. Local artists were commissioned to design and transform 28 sculptural boat sails, applying original artwork to both the front and back of each piece.
Throughout the summer months, these dual-sided maritime sculptures have lined the streets of downtown Sturgeon Bay, adorning public thoroughfares on both the east and west sides of the canal. Among the notable creations displayed this season is "Just Bee...," a unique piece designed by artist Natalie Townsend that spent the summer outside Novel Bay Booksellers before entering the weekend auction schedule.
This year's focus on sails represents the latest chapter in a long-standing creative tradition for Destination Sturgeon Bay. In past years, the public art program has highlighted various regional cultural touchstones through different sculptural canvases, including lighthouses, sturgeon, bass, native cherries, and Adirondack-style deck furniture fondly branded as "Chair-ies."
Art collectors and local supporters will have the opportunity to acquire the sails through a dedicated virtual auction operated via the Handbid mobile application. Bidding remains open until 5:30 p.m. on Saturday, Sept. 19. Prospective buyers can track real-time bid updates through the digital platform, and full galleries of the artwork alongside direct bidding links are hosted on Destination Sturgeon Bay’s official event web portal.
To foster greater engagement between the community and the creators, festival organizers have introduced a new Friday opening reception scheduled for Sept. 18 from 4 to 6 p.m. Hosted along the West Side waterfront at the Door County Granary, the event allows attendees to view the sails assembled along the waterfront promenade, hear live artist interviews, and purchase refreshments, including wine, beer, and light fare from the Granary Wharf Cafe.
Waterfront activities on Friday evening will also feature family-oriented entertainment, headlined by complimentary Ferris wheel rides operating from 5 to 8 p.m. This visual centerpiece invites visitors to enjoy scenic harbor views while celebrating the official start of the autumn festival weekend.
Automotive enthusiasts will also notice an updated schedule on Friday with the debut of the Old Bolts Car Club Cruise-In Meet & Greet. Starting at 5 p.m. at The Lodge at Leathem Smith, located at 1640 Memorial Drive, this gathering replaces the club’s previous tradition of a Friday evening downtown driving tour, offering attendees a venue with food and beverage service to preview classic vehicles.
The car club's primary showcase unfolds on Saturday, Sept. 19, with the 20th annual Harvest Fest Car Show. More than 100 antique, classic, and custom automobiles are anticipated to line South Third Avenue, filling the downtown corridor between Michigan Street and Quincy Street from 8 a.m. to 4 p.m.
Vehicle owners wishing to display their cars can register on-site Saturday between 8 a.m. and noon at the intersection of South Third Avenue and Nebraska Street for an entry fee of $15. The exhibition officially commences at 10 a.m. with a ceremonial presentation of the American colors and the singing of "The Star-Spangled Banner," concluding later in the afternoon with an awards presentation scheduled for 3 p.m.
Simultaneously, seasonal German-style revelry will take place on North Third Avenue outside Starboard Brewing Co., highlighted by the traditional Tapping of the Oktoberfest Firkin. Sturgeon Bay Mayor David Ward will lead the noon tapping ceremony, releasing a specialty craft beer created specifically for the gathering.
The brewery festivities will continue throughout Saturday afternoon with a series of physical challenges and novelty contests. Following the firkin tapping, adult participants will test their endurance at 1 p.m. in the classic arm's-length beer stein-holding contest. Younger attendees can join a dedicated root beer holding competition at 2 p.m., leading into the 3 p.m. "Beer Puppeteer" challenge, where contestants must navigate a string-operated rig to drink from a cup of beer.
With Saturday programming expanding further across the West Side waterfront near the Door County Granary, Harvest Fest continues to evolve into a multifaceted regional destination. By weaving together local artistry, automotive culture, and lively downtown traditions, the weekend provides a welcoming launchpad for Door County's autumn festival season.
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