Fall festival season is starting to take over Wisconsin—and this weekend offers an unusually entertaining mix.
You can eat free watermelon in Pardeeville and free sweet corn in Darien, listen to bluegrass on the East Troy Village Square, celebrate Oktoberfest a little early in Waunakee and Waupaca, watch working sheepdogs in Jefferson or follow Highway 35 to Laura Ingalls Wilder’s hometown of Pepin.
Then we’re looking ahead to September 18–20, when several of Wisconsin’s major fall traditions return, including Wo-Zha-Wa in Wisconsin Dells, Maple Fall Fest in Marshfield, Cedarburg’s Wine & Harvest Festival and a growing Italian celebration on Kenosha’s lakefront.
Here are 15 Wisconsin events worth building a road trip around from September 11–20, 2026.
THIS WEEKEND: SEPTEMBER 11–13
1. Pardeeville Watermelon Festival — Pardeeville
Saturday, September 12, 9:30am–4pm
Road trip routes: Highways 22 & 44
Watermelon in September? Pardeeville has been doing it since 1968.
The 58th annual Pardeeville Watermelon Festival takes over Chandler Park Saturday with watermelon eating, carving and the appropriately sticky U.S. Watermelon Speed-Eating and Seed-Spitting Championships.
Even better, there’s free watermelon. Food, refreshments and children’s activities fill out the day.
It’s exactly the kind of unusual small-town Wisconsin tradition that’s worth seeking out on a road trip—and Pardeeville sits conveniently between Portage and Beaver Dam.
2. Wisconsin Sheep & Wool Festival — Jefferson
September 11–13
Road trip routes: Highways 26, 89 & 106
This festival turns out to be considerably more entertaining than simply looking at wool.
The Wisconsin Sheep & Wool Festival fills Jefferson County Fair Park with sheep shows, shearing demonstrations, fiber arts, workshops, competitions and more than 100 vendors.
One highlight is the Crook & Whistle Stock Dog Trial, where highly trained dogs demonstrate the remarkable skills involved in moving livestock. Shearing demonstrations and opportunities to learn about different sheep breeds continue throughout the weekend.
If you’ve never watched a good sheepdog work, this might surprise you.
3. Darien Corn Fest — Darien
September 11–13
Road trip routes: I-43, U.S. 14 & Highway 11
Darien has a simple but effective formula for attracting festivalgoers: give them sweet corn.
The 65th annual Darien Corn Fest brings carnival rides, live music, a craft fair, softball and volleyball, Friday-night fireworks and plenty of food to West Park. Then comes the main attraction: free sweet corn Saturday and Sunday.
Sunday features an antique tractor pull followed by the Corn Fest Parade with floats, bands, tractors and horses.
Darien is only about 20 minutes from Lake Geneva, so this one pairs easily with a southeastern Wisconsin road trip.
4. HINDER Fest — Waupaca
Saturday, September 12, 11:30am–10pm
Where: H.H. Hinder Brewing Company
Road trip routes: U.S. 10, Highways 22, 49 & 54
Waupaca’s H.H. Hinder Brewing Company welcomes fall Saturday with an all-day celebration of beer, music and Oktoberfest-style fun – one of our favorite Wisconsin events tied in with a brewery!
HINDER Fest includes live music from EMBER and The Squeezettes, brewery tours, food from the Waupaca Lions Club and Moose Inn, Hammerschlagen and a ceremonial keg tapping. The day also marks the anticipated annual release of Hinder’s PROSTerior Oktoberfest, followed by the wonderfully named BUTT Lift stein-holding contest.
Combine it with a drive through Waupaca and the nearby Chain O’ Lakes and you’ve got yourself a pretty good Saturday.
5. East Troy Bluegrass Festival — East Troy
September 12–13
Where: Historic East Troy Village Square
Road trip routes: I-43, Highways 20 & 120
Bluegrass takes over the historic Village Square during the 32nd annual East Troy Bluegrass Festival.
The festival has been bringing bluegrass to southeastern Wisconsin since 1994 and describes itself as the longest-running bluegrass festival in Wisconsin.
Twelve bands perform across the weekend. Saturday’s lineup includes Genesee Ridge, Coffee Creek, Piper Road Spring Band and headliner Lonesome River Band, while Sunday’s music culminates with Nick Chandler and Delivered. There’s also a Saturday Band Scramble and Sunday’s gospel service.
Bring a lawn chair and settle in on the square.
6. Wauktoberfest — Waunakee
September 11–13
Road trip routes: U.S. 12, Highways 19 & 113
Beer, brats and polka music are only the beginning at Wauktoberfest. I mean, really, those three things are cornerstones of Wisconsin events!
Waunakee’s 22nd annual German celebration features authentic food, German beer, music and dancing on a wooden dance floor along with a collection of competitions that get increasingly entertaining. There’s a Saturday beer tasting, Sunday’s Sausage Shuffle 5K, sauerkraut eating, the Frau Carry and the crowd-favorite Dachshund Dash.
Nothing says Oktoberfest quite like watching very short-legged dogs run very fast. And the Badgers don’t even play until the evening! Highway 19 & 113 bring you into the “only Waunakee in the world.”
7. Autumn Fest & Classic Auto Show — Baileys Harbor
Saturday, September 12, 9am–4pm
Road trip route: Highway 57
Door County begins shifting from summer into fall with Autumn Fest in Baileys Harbor.
Classic cars and motorcycles gather around the Town Hall while arts and crafts vendors, food, drinks and live music fill out the day.
And this one practically begs to become a larger road trip. Follow Highway 57 up the Lake Michigan side of Door County, enjoy Autumn Fest, then loop around the peninsula using Highway 42.
8. Cameron Bluegrass Festival — Cameron
September 11–13
Where: Pioneer Village Museum
Road trip routes: U.S. 8 & U.S. 53
East Troy isn’t the only Wisconsin destination going bluegrass this weekend.
The Cameron Bluegrass Festival celebrates its 20th anniversary with three days of music at the Pioneer Village Museum near Rice Lake. National and regional bands perform alongside workshops, informal jam sessions, vendors and food.
The lineup includes The Kody Norris Show, Little Roy & Lizzy Show and Art Stevenson & High Water, with music continuing Friday evening through Sunday afternoon.
Your admission also includes access to the Pioneer Village Museum buildings, making this one a nice combination of music and Wisconsin history.
9. Laura Ingalls Wilder Days — Pepin
September 12–13
Road trip route: Highway 35
Follow Wisconsin’s Great River Road to the birthplace of one of America’s best-known authors.
Laura Ingalls Wilder Days celebrates the life and legacy of the Little House author with traditional crafts, Pa’s Fiddle music, a spelling bee, children’s activities, historical demonstrations, food and a Sunday parade.
You can also visit the reconstructed Little House in the Big Woods on the property where Laura was born in 1867.
Highway 35 along Lake Pepin is one of Wisconsin’s great scenic roads, so even getting there is part of the experience. And hit up The Pickle Factory and Villa Belezza Winery while you’re there!
10. Wausau Festival of Arts — Wausau
September 12–13
Where: Downtown Wausau
Road trip routes: I-39/U.S. 51, Highways 29 & 52
Downtown Wausau becomes one giant outdoor gallery during the Wausau Festival of Arts.
Founded in 1965, it’s now central Wisconsin’s largest outdoor art festival, bringing more than 100 juried fine artists downtown with ceramics, fiber, painting, sculpture, jewelry, glass, photography and other works.
Live performances take place on the 400 Block stage and throughout the shopping area, while food vendors support Wausau-area nonprofit organizations.
Festival hours are 10am–5pm Saturday and 10am–4pm Sunday, with free parking nearby.
LOOKING AHEAD: SEPTEMBER 18–20
11. Wo-Zha-Wa Fall Festival — Wisconsin Dells
September 18–20
Road trip routes: I-90/94, U.S. 12, Highways 13, 16 & 23
When Wo-Zha-Wa arrives, you know Wisconsin’s fall-festival season is officially underway.
Downtown Wisconsin Dells fills with an arts and crafts fair, antique and collectibles market, Maxwell Street Days, farmers market, carnival rides, food and live entertainment throughout the three-day weekend.
Sunday’s traditional 1:30 p.m. Wo-Zha-Wa Parade provides the big finale.
The festival itself is free—and since you’re already in Wisconsin Dells, finding more things to do shouldn’t be difficult.
12. Maple Fall Fest — Marshfield
September 19–20
Where: Wildwood Park & Zoo
Road trip routes: U.S. 10, Highways 13 & 97
Marshfield welcomes fall with one of central Wisconsin’s major arts-and-crafts weekends!
Maple Fall Fest brings more than 150 arts and crafts vendors to Wildwood Park along with children’s activities, Amish specialties, a beer garden, food court and even a potato pancake breakfast. Admission is free.
Hours are 9am–5pm Saturday and 10am–4pm Sunday. And with the free Wildwood Zoo right there, it’s easy to turn Maple Fall Fest into a full day in Marshfield.
13. River Fest — Sheboygan
Saturday, September 19, 11am–5pm
Where: Riverfront Drive Boardwalk
Road trip routes: I-43, Highways 23, 28 & 42
Sheboygan’s riverfront gets its own festival Saturday with River Fest, a free celebration stretching along the Riverfront Drive Boardwalk.
Live music includes Minor Worries and the Buffalo Joe Band, joined by children’s entertainment, local vendors, food trucks and a family activity area.
One particularly cool offering: U.S. Coast Guard boat tours are scheduled from 11:30am–3:30pm.
The boardwalk setting also puts you among Sheboygan’s riverfront restaurants and shops, with Lake Michigan only minutes away.
14. Cedarburg Wine & Harvest Festival — Cedarburg
September 19–20
Road trip routes: I-43 & Highway 60
Historic downtown Cedarburg welcomes autumn with one of southeastern Wisconsin’s biggest fall celebrations.
The Wine & Harvest Festival runs 10am–6pm Saturday, with the main stage continuing until 9pm, and 10am–5pm Sunday.
Washington Avenue fills with vendors, food, live entertainment and harvest-themed activities against the backdrop of Cedarburg’s historic downtown.
One travel note for 2026: portions of Washington Avenue are under construction, so festival organizers are warning visitors about traffic rerouting and reduced street parking.
Plan ahead—and then enjoy one of Wisconsin’s classic fall-festival towns.
15. Kenosha Italian Fest — Kenosha
September 18–20
Where: Celebration Place at HarborPark
Road trip routes: I-94, Highways 32, 50 & 158
Kenosha Italian Fest returns for its second year—and it’s already getting considerably bigger.
The three-day lakefront celebration features Italian food and desserts, live music on two stages, cooking demonstrations, bocce, a Heritage Tent, roaming Sicilian Serenaders and family activities.
Saturday brings the Kenoshans of Italian Descent Parade at 11am and fireworks later that night. Sunday begins with an outdoor Mass at 10am before the festival reopens at 11.
New additions for 2026 include a much larger Italian American Society food tent, more Italian food vendors, an expanded dessert tent with gelato and Italian ice, bocce courts and a Friday-night opening mixer.
Admission is $5 per day, with a $10 weekend pass planned.
And since it’s all happening beside Lake Michigan at HarborPark, you can easily combine Italian Fest with downtown Kenosha, the museums and the lakefront.
Pick Some Roads and GO!
This is one of those Wisconsin weekends when deciding where to go may be harder than finding something worth doing.
You can spit watermelon seeds in Pardeeville, eat free corn in Darien, drink Oktoberfest beer in Waupaca, listen to bluegrass in East Troy, watch sheepdogs work in Jefferson, admire classic cars in Door County or follow the Mississippi to Laura Ingalls Wilder’s hometown.
Then one week later, Wo-Zha-Wa, Maple Fall Fest, River Fest, Cedarburg Wine & Harvest Festival and Kenosha Italian Fest give you five more excellent reasons to hit the road.
September has arrived—and Wisconsin fall road-trip season is officially underway.
