This week’s featured events: Sister Bay Fall Fest, Hunting Moon Pow Wow, Eau Claire Hmong New Year, Elkhorn Oktoberfest, Wisconsin Dells Fall Tap Takeover, Racine Fall Wine Walk, the Fall Art Tour, Wisconsin Science Festival, Ashland Harvest Fest and Kohler Food & Wine.
October is hitting its stride in Wisconsin, and the fall festivals calendar isn’t slowing down!
Door County celebrates the 80th anniversary of Sister Bay Fall Fest. Milwaukee welcomes Native American dancers and drummers for the Hunting Moon Pow Wow. Eau Claire celebrates Hmong culture and traditions. Elkhorn breaks out the lederhosen, Wisconsin Dells taps the craft beer, and Racine offers another opportunity to sip and stroll downtown.
Meanwhile, you can explore artists’ studios along scenic back roads, celebrate the harvest near Lake Superior, and look ahead to one of Wisconsin’s premier culinary events.
Here are 10 Wisconsin festivals and events worth building a road trip around October 16–23, 2026, including a few celebrations continuing into the following weekend.
1. Sister Bay Fall Fest — Sister Bay
October 16–18 | Downtown Sister Bay
Road trip routes: Highways 42 & 57
This is the big one!
The 80th annual Sister Bay Fall Fest takes over this picturesque Door County community for three days of live music, food, entertainment, carnival rides and a huge arts and crafts fair featuring more than 100 vendors.
Saturday’s Fall Fest Parade begins at 11 a.m. Sunday brings the popular Derby Race at 10 a.m. and the traditional Ping Pong Ball Drop at 2 p.m.
Live music fills venues throughout town, including Al Johnson’s Stabbur, Husby’s, Sister Bay Bowl and Peach Barn Brewing. Friday’s festivities also include a traditional Door County fish boil.
Admission is free.
And since you’re already in Sister Bay, take time to explore the waterfront, marina, shops and restaurants. Highway 42 continues north toward Ellison Bay and Gills Rock, providing more opportunities to enjoy Door County’s fall scenery. Sister Bay Door County
More information: Official Sister Bay Fall Fest schedule
State Trunk Tour connection: Explore Wisconsin Highway 42
2. Hunting Moon Pow Wow — Milwaukee
October 16–18 | Baird Center, Downtown Milwaukee
Road trip routes: I-43, I-94, I-794
One of Milwaukee’s most colorful cultural celebrations returns this weekend.
The Hunting Moon Pow Wow brings Native American dancers, singers and drummers together for three days of competition, celebration and cultural traditions.
Held at the Baird Center in downtown Milwaukee, the event welcomes visitors to experience the music, dancing, regalia and traditions of Native American communities.
The gathering also provides an opportunity to learn about Native American history and culture while experiencing the excitement of competitive dancing and drumming.
Admission is free, making this a particularly accessible cultural event for families and visitors. Welcome to the Baird Center!
More information: Hunting Moon Pow Wow at the Baird Center
3. Eau Claire Hmong New Year — Eau Claire
October 17–18, 7am–4:30pm | Sonnentag Event Center
Road trip routes: I-94, U.S. 12, Highways 37 & 93
Eau Claire celebrates the traditions and heritage of its Hmong community during the annual Eau Claire Hmong New Year.
This year’s celebration is particularly meaningful, commemorating 50 years of the Hmong community in the Chippewa Valley.
The two-day event includes traditional foods, cultural performances, arts and crafts vendors, competitions and entertainment.
More than 4,000 people attended last year’s celebration, and organizers are planning an even bigger event for 2026.
The Hmong New Year is an important cultural celebration connected with the harvest season, family gatherings and the preservation of traditions.
The Sonnentag Event Center is located along Menomonie Street, just west of downtown Eau Claire. Eau Claire Hmong New Year
More information: Official Eau Claire Hmong New Year website
4. Elkhorn Oktoberfest — Elkhorn
Saturday, October 17, 9am–5pm | Downtown Elkhorn
Road trip routes: I-43, U.S. 12, Highways 11 & 67
Along with other fall festivals, Oktoberfest season isn’t finished yet!
Downtown Elkhorn hosts its 21st annual Oktoberfest, bringing German-inspired food, beer, music and activities to the historic courthouse square.
The festival features craft vendors, live entertainment, an annual classic car show and the popular All Around Town Beer/Wine Tasting, which takes visitors into participating downtown businesses.
There’s also an Oktoberfest 5K Run/Walk and plenty of opportunities to enjoy brats, pretzels and seasonal beverages.
Admission to the festival is free.
Elkhorn’s location makes it an easy road trip from Lake Geneva, Delavan, Burlington and much of southeastern Wisconsin.
Prost!
More information: Elkhorn Oktoberfest from Travel Wisconsin
5. Dells On Tap: Fall Tap Takeover — Wisconsin Dells
October 16–17 | Downtown Wisconsin Dells
Road trip routes: I-90/94, U.S. 12, Highways 13, 16 & 23
Wisconsin Dells celebrates the state’s craft brewing industry with an entire weekend devoted to beer.
Dells On Tap begins Friday with the Craft Beer Walk, followed Saturday by the Fall Tap Takeover, featuring regional breweries and opportunities to sample seasonal beers while meeting the people who make them.
Saturday’s main tasting runs 1–5 p.m., with VIP admission beginning at 11:30 a.m.
There’s also a beer-themed costume contest called Dress to the Pints, featuring cash prizes for the most creative outfits.
General admission for Saturday is $60, with combination tickets available for both events.
And Wisconsin Dells in mid-October provides plenty of other attractions, scenic drives and opportunities to explore the Wisconsin River corridor. Wisconsin Dells
More information: Official Dells On Tap event information
6. Fall Wine Walk — Racine
Saturday, October 17, 1–6pm | Downtown Racine
Road trip routes: I-94, Highways 20, 32 & 38
If you missed last Saturday’s Fall Wine Walk in downtown Racine, here’s another chance!
The second Fall Wine Walk takes place October 17, offering visitors an opportunity to explore downtown shops and businesses while sampling wines and other beverages.
The event features 30 participating downtown businesses, with 20 wine samples and 10 beer, cider or seltzer samples.
General admission is $40 and includes a sampling glass, canvas tote and snacks along the route.
It’s a great opportunity to discover downtown Racine’s historic architecture, restaurants and shops while enjoying a leisurely October afternoon.
And Lake Michigan’s shoreline is only a few blocks away. Visit Racine County –
More information: Downtown Racine Fall Wine Walk
7. Fall Art Tour — Mineral Point, Spring Green, Dodgeville & Baraboo
October 16–18, 10am–6pm daily
Road trip routes: U.S. 18/151, Highways 23, 33, 39 & 78
Here’s an event that seems practically designed for State Trunk Tour!
The annual Fall Art Tour sends visitors exploring the scenic hills and valleys of southwestern Wisconsin, stopping at artists’ studios scattered throughout Mineral Point, Spring Green, Dodgeville and Baraboo.
More than 60 artists participate, demonstrating pottery, woodworking, painting, sculpture, jewelry making, fiber arts and other creative skills.
The best part? You create your own itinerary.
Download the tour map, follow the signs and explore as many studios as you’d like. Many participating studios are located along rural roads surrounded by some of Wisconsin’s most impressive fall scenery.
Admission is free, and no reservations are required.
This is one of those events where the drive between destinations is half the fun. Fall Art Tour
More information: Official Fall Art Tour and interactive map
8. Wisconsin Science Festival — Madison & Statewide
October 15–25 | Madison and locations across Wisconsin
Road trip routes: I-39/90/94, U.S. 12/18, U.S. 151
Here’s something a little different for the festival calendar.
The Wisconsin Science Festival celebrates science, technology, engineering, art and mathematics through hundreds of activities and events across Wisconsin.
The festival’s 2026 theme is “Us!”, focusing on the science of humans, including our brains, bodies, place in the universe and the discoveries that shape our lives.
Activities include hands-on demonstrations, exhibits, tours, workshops, performances and educational programs.
Madison serves as a major hub for the festival, including activities connected with UW–Madison and the Wisconsin Institute for Discovery.
Many events are free, although individual programs may have different admission requirements.
And because the festival runs through October 25, there are opportunities to explore it both this weekend and next. Visit Madison
More information: Official Wisconsin Science Festival event calendar
9. Ashland Harvest Fest — Ashland
Saturday, October 17, 10am–9pm
Where: 710 11th Avenue East
Road trip routes: U.S. 2, Highway 13; Highway 112 nearby
Lake Superior’s south shore celebrates autumn during the third annual Ashland Harvest Fest.
The festival features live music, a barn dance, food trucks, local artisans, a farmers market, apple cider pressing and plenty of family-friendly activities.
There’s also a beer garden and the Great Harvest Bake-Off, where participants compete for prizes with their favorite creations.
Admission is free.
Ashland makes a particularly appealing fall road-trip destination because of its location along Lake Superior.
Follow U.S. 2 along the lakeshore, explore the historic downtown or continue north on Highway 13 toward Washburn and Bayfield.
And if you’re looking for an additional stop, State Trunk Tour has featured South Shore Brewery in Ashland and Washburn, another good reason to explore the area. Travel Wisconsin
More information: Ashland Harvest Fest from Travel Wisconsin
10. Kohler Food & Wine — Kohler
October 22–25 | Kohler
Road trip routes: I-43, Highways 23, 28 & 42 nearby
Looking ahead into next weekend, one of Wisconsin’s premier culinary celebrations returns to Kohler.
Kohler Food & Wine celebrates its 25th anniversary in 2026, bringing acclaimed chefs, winemakers and culinary enthusiasts together for a series of special events.
The festival includes cooking demonstrations, wine tastings, chef experiences and opportunities to explore food and beverages from some of the country’s most accomplished culinary professionals.
The setting adds considerably to the experience, with events taking place around Kohler’s renowned resort properties.
Tickets and overnight packages are available, although some experiences and accommodations may sell out.
Kohler is located just west of Sheboygan along Highway 23, making this an easy destination from Milwaukee, Green Bay and other eastern Wisconsin communities. Kohler Wisconsin
More information: Official Kohler Food & Wine website
Pick Some Roads and GO!
This weekend offers an impressive variety of ways to experience Wisconsin.
You can celebrate 80 years of Fall Fest in Door County, experience Native American traditions in Milwaukee, celebrate Hmong heritage in Eau Claire, hoist a stein in Elkhorn or sample craft beers in Wisconsin Dells.
Explore artist studios along the winding roads of southwestern Wisconsin. Sip your way around downtown Racine. Head toward Lake Superior for Ashland’s Harvest Fest. Or get curious about the world around you during the Wisconsin Science Festival.
And looking ahead, Kohler Food & Wine provides another excellent reason to hit the road.
The leaves are changing, the temperatures are cooling and Wisconsin’s festival calendar is still packed.
Pick Some Roads and GO!!
