Sure, summer is still officially here through Tuesday, but fall festival season is officially hitting its stride in Wisconsin.
This weekend brings one of the state’s best-known fall traditions to Wisconsin Dells, more than 150 artists and craftspeople (and lots of maple syrup) to Marshfield, wine and grape stomping to Cedarburg, Italian food and fireworks to Kenosha, a huge downtown street party to Racine and a new culinary festival to Milwaukee’s lakefront.
Throw in Oktoberfest celebrations, Door County’s first big harvest festival of the season and a riverfront celebration in Sheboygan and you’ve got plenty of reasons to Pick Some Roads and GO!!
Here are 10 Wisconsin festivals and events worth building a road trip around September 18–20, 2026.
1. Wo-Zha-Wa Fall Festival — Wisconsin Dells
September 18–20
Road trip routes: I-90/94, U.S. 12, Highways 13, 16 & 23
One of Wisconsin’s great fall festival traditions takes over downtown Wisconsin Dells this weekend.
Wo-Zha-Wa packs three days with a huge arts and crafts fair, antique and collectibles market, sidewalk sales, farmers market, food, live entertainment and carnival rides. Friday gets things rolling before virtually everything expands Saturday.
Saturday morning also brings the Wo-Zha-Wa 5K and 10K, with runners following a scenic route along the Wisconsin River before climbing the locally famous “Turkey Hill.”
Sunday’s finale is the 1:30 p.m. Wo-Zha-Wa Parade, featuring more than 60 units followed by a performance from Chicago’s South Shore Drill Team.
And since you’re already in Wisconsin Dells, finding something else to enjoy on top of Wo-Zha-Wa Days isn’t too difficult.
2. Maple Fall Fest — Marshfield
September 19–20
Where: Wildwood Park & Zoo
Road trip routes: U.S. 10, Highways 13 & 97
Marshfield’s Maple Fall Fest brings more than 150 handmade arts and crafts vendors to beautiful Wildwood Park for two full days of Wisconsin fall fun.
The festival also includes Amish specialties, maple products, a food court, beer garden, children’s activities and entertainment. Mad Dog & Merrill bring their “Grillin’ Buddies” show both days, while Sunday’s schedule includes a Marshfield Monarchs butterfly release.
And yes, there’s the legendary breakfast featuring regular and potato pancakes, scrambled eggs, maple sausage and Wisconsin cheese curds.
Festival admission itself is free, and Wildwood Park & Zoo provides another good reason to spend some time exploring Marshfield. We cover all of that in our latest State Trunk Tour Podcast, too!
Visit Marshfield’s Maple Fall Fest guide
3. Cedarburg Wine & Harvest Festival — Cedarburg
September 19–20
Road trip routes: I-43, Highway 60
Historic downtown Cedarburg celebrates the harvest with one of southeastern Wisconsin’s signature fall festivals.
The Wine & Harvest Festival fills downtown with local wines, seasonal foods, artisan vendors, live music and one of the festival’s most popular traditions: grape stomping.
Hours are 10 a.m.–6 p.m. Saturday, with the main stage continuing until 9 p.m., and 10 a.m.–5 p.m. Sunday.
One important 2026 travel note: construction along portions of Washington Avenue is causing traffic rerouting and reducing some local street parking, so give yourself a little extra time getting into town.
Cedarburg Wine & Harvest Festival official site
4. Kenosha Italian Fest — Kenosha
September 18–20
Where: Celebration Place at HarborPark
Road trip routes: I-94, Highways 32, 50 & 158
After a successful inaugural year, Kenosha Italian Fest returns considerably bigger for 2026.
The lakefront festival offers authentic Italian food and desserts, live music on two stages, cooking demonstrations, bocce, a Heritage Tent, Sicilian Serenaders and family activities throughout the weekend.
Saturday begins with the Kenoshans of Italian Descent & Friends Parade at 11 a.m., followed by a full day of music and fireworks over the lakefront Saturday evening. Sunday starts with an outdoor Mass at 10 a.m.
New additions include an expanded dessert tent with gelato and Italian ice, more Italian food vendors and a larger Italian American Society food tent.
Admission is $5 daily or $10 for a weekend pass.
Kenosha Italian Fest official schedule
5. Green County Cheese Days – Monroe
Friday – Sunday, September 18-20
Where: Downtown Monroe
Road trip routes: Highways 11, 59, 69 & 81
Monroe is an epicenter of cheesemaking in the heart of Green County – even their high school team name is the “Cheesemakers.” The city and county celebrates every other year Green County Cheese Days, a three-day hullabaloo filled with food, music, dancing, contests, crafts, cheesemaking, cow milking, yodeling, and even Wisconsin’s only parade led by Brown Swiss Cows. Green County Cheese Days is ready for 2026, happening September 18th through the 20th.
This semi-annual event is BIG one in southern Wisconsin. If you love cheese and partying, Monroe is a great destination this weekend!
6. Party on the Pavement — Racine
Saturday, September 19, Noon–7pm
Where: Downtown Racine
Road trip routes: I-94, Highways 20, 32 & 38
How about a festival that’s 12 blocks long?
Downtown Racine’s Party on the Pavement returns for its 23rd year with multiple stages of live music, more than 20 food trucks, shopping, street performers, games and activities stretching along Main and Sixth Streets. Admission is free.
Look for BMX stunt shows, hip-hop and breakdance battles, a classic car show, axe throwing and a new Mini-German Fest featuring Bavarian music and German food.
The Racine Art Museum also offers free admission and hands-on art activities during the festival.
This is easily one of southeastern Wisconsin’s biggest street parties of the year – hopefully the weather holds out!
Party on the Pavement official information
7. River Fest — Sheboygan
Saturday, September 19, 11am–5pm
Where: Riverfront Drive Boardwalk
Road trip routes: I-43, Highways 23, 28 & 42
Sheboygan’s Riverfront Drive Boardwalk gets its own celebration Saturday during River Fest.
The free one-day festival runs along the Sheboygan River with live entertainment, local food, vendors and children’s activities in a family-friendly waterfront setting.
One of the nice things about this one is the location. You’re already among the shops and restaurants lining the riverfront, with Lake Michigan, South Pier and downtown Sheboygan all nearby.
It makes an easy Saturday road trip—and an equally easy excuse to spend the rest of the day exploring Wisconsin’s Malibu of the Midwest.
8. Harvest Fest — Sturgeon Bay
Saturday, September 19, starting at 9am
Where: Downtown Sturgeon Bay
Road trip routes: Highways 42 & 57
Door County’s fall festival season gets underway Saturday with Harvest Fest in downtown Sturgeon Bay.
Third Avenue closes to traffic for a craft fair, food vendors, shopping specials and live music. At noon, the mayor performs the official Tapping of the Oktoberfest Firkin, followed at 1 p.m. by a stein-holding contest. Kids get their own root-beer-holding competition at 2 p.m.
Admission is free.
And because this is Door County in September, Harvest Fest can easily become the starting point for a much larger Highway 42/57 road trip.
Wine lovers can also head just north of town to Parallel 44 Vineyard & Winery’s Harvest Fest, where Saturday brings wine, food, live music, winery tours and traditional grape stomping.
Destination Door County’s Harvest Fest information
9. Freshwater Food & Wine Festival — Milwaukee
September 19–20
Where: Henry Maier Festival Park
Road trip routes: I-43, I-794, Highway 32
There’s something new happening at Milwaukee’s lakefront this weekend.
The inaugural Freshwater Food & Wine Festival takes over Henry Maier Festival Park with nationally recognized chefs, local restaurants, wines and craft beverages, celebrity-chef challenges, live entertainment and culinary experiences.
General admission provides access to the festival grounds, marketplace, entertainment and main-stage programming; food, wine and specialty beverage experiences are then available à la carte.
After a summer filled with ethnic festivals, this gives Milwaukee’s lakefront festival grounds a decidedly culinary twist heading into fall.
Freshwater Food & Wine Festival official site
10. Art in the Park — Stevens Point
Saturday, September 19, 10am–4pm
Where: Pfiffner Pioneer Park
Road trip routes: I-39/U.S. 51, U.S. 10, Highway 66
The Wisconsin River provides the backdrop for the 56th annual Art in the Park in downtown Stevens Point.
Artists and craftspeople gather in Pfiffner Pioneer Park to sell their work, demonstrate their skills and offer hands-on art activities for kids.
The location makes this especially nice for a September road trip: the park sits right along the river and the Green Circle Trail, with downtown Stevens Point only a few blocks away.
And if you stick around after dark, head to the Stevens Point Sculpture Park for LIT from 7–9 p.m., when illuminated sculptures, projection mapping, dance and music transform the park for the evening.
11. Baraboo Oktoberfest — Baraboo
Saturday, September 19, 3–9pm
Where: Circus World
Road trip routes: U.S. 12, Highways 33 & 136
Baraboo celebrates the Ringling family’s German heritage with an Oktoberfest in a rather appropriate location: Circus World.
Local breweries pour Oktoberfest beers while food trucks serve dinner, and three musical groups provide the soundtrack. Bratwurst and pretzels naturally make appearances, too.
Baraboo Oktoberfest runs from 3–9 p.m., making it easy to combine with a daytime visit to Devil’s Lake State Park, downtown Baraboo or even nearby Wo-Zha-Wa in Wisconsin Dells.
Prost!
12. Road America Art on Wheels Weekend with VSCA – Elkhart Lake
Friday – Sunday, September 18-20
Where: Road America
Road trip routes: Highway 67
The Art On Wheels Weekend featuring VSCDA draws vintage racers from across the U.S. as they take to the track September 18th-20th at Road America. Over 300 meticulously restored vintage and historic race cars, spanning 11 racing classes, will grace the iconic Road America track, presenting a mesmerizing journey through automotive history. From the graceful curves of classic sports cars to the raw power of muscle machines, every era and every passion will be showcased.
A unique highlight of the event is the open-access paddock, inviting spectators to immerse themselves in the world of vintage racing. This is a rare opportunity to get up close and personal with these magnificent racing machines, each prepared to era specifications, and witness the dedication and craftsmanship of maintaining these automotive treasures.
Get updates and tickets on the Road America website. Anyone 16 and under gets in FREE with a paying adult. You can take advantage of that offer at the gate with proof of age. Racing runs rain or shine.
You’ll find Road America along Highway 67 just north of Highway 23 and Plymouth and just west of Highway 57 in Sheboygan County.
Pick Some Roads and GO!
This might be one of the easiest weekends of the year to simply choose a direction and find something interesting.
Head toward Lake Michigan for Italian Fest in Kenosha, Party on the Pavement in Racine, Freshwater Food & Wine in Milwaukee or River Fest in Sheboygan.
Point the car west for Oktoberfest in Baraboo. Follow U.S. 10 toward Art in the Park in Stevens Point. Take Highway 13 into Marshfield for Maple Fall Fest. Or head north on Highways 42 and 57 as Door County’s harvest season gets underway.
And right in the middle of it all, Wisconsin Dells is throwing one of the state’s biggest fall parties at Wo-Zha-Wa.
The temperatures are getting more comfortable, Wisconsin’s first hints of fall color aren’t far away and the festival calendar is packed.
Sounds like road-trip season to us.
Pick Some Roads and GO!!
