If you were waiting for Wisconsin’s fall festival season to really get rolling, this is the weekend.
Cranberries take over an entire town near Tomah. La Crosse breaks out the lederhosen for one of the Midwest’s biggest Oktoberfests. Gays Mills celebrates the apple harvest, New Glarus taps the Staghorn, Minocqua smells like roasting beef and some truly enormous pumpkins arrive near Eau Claire.
And looking into next week, one of the world’s premier dairy events brings people from across the globe to Madison.
Here are 10 Wisconsin festivals and events worth building a road trip around September 24 through October 2, 2026.
1. Warrens Cranberry Festival — Warrens
September 25–27, 7am–5pm daily
Road trip routes: I-94, U.S. 12; Highways 21 & 173 nearby
For three days every September, the little Monroe County community of Warrens becomes a considerably larger place.
The 53rd annual Warrens Cranberry Festival celebrates Wisconsin’s cranberry industry with more than three miles of shopping and over 1,200 booths, including arts and crafts, flea and antique vendors, farm-market stands and plenty of cranberry-flavored food. The festival itself lists 800 arts-and-crafts vendors alone.
Self-guided cranberry-marsh walking tours run Friday and Saturday from 8am–3pm and Sunday from 10am–noon, giving visitors a chance to see where one of Wisconsin’s signature crops actually comes from. Sunday’s big parade steps off at 1pm.
State Trunk Tour has been there, and yes: the festival really does take over the whole town.
Admission is free. Getting there is easy: follow I-94 to Exit 135 near Three Bears Resort, with U.S. 12 running nearby.
Warrens Cranberry Festival official site
2. Oktoberfest USA — La Crosse
September 24–27
Where: Oktoberfest Grounds, downtown La Crosse
Road trip routes: I-90, U.S. 14/61 & Highway 35
Break out the lederhosen. Oktoberfest USA is back!
La Crosse has been celebrating Oktoberfest since 1961, making this the longest-running Oktoberfest in the Midwest. Four days bring German music, food, beer, parades, competitions and plenty of Gemütlichkeit to the Oktoberfest Grounds near downtown.
Saturday is particularly big. The Maple Leaf Parade begins at 10am, followed by festivities at the grounds from 11am until midnight and Lederhosen Games during the afternoon.
I-90, U.S. 53, U.S. 14/61, and Highways 16, 33, and 35 all bring you to La Crosse. We highly recommend drives through the Driftless Area on Highways 16, 33, and 35, including along the Great River Road. It makes the journey almost as much fun as the destination! Kind of like what the State Trunk Tour is all about.
Prost!
3. Beef-A-Rama — Minocqua
Saturday, September 26
Road trip routes: U.S. 51 & Highway 70
Only Wisconsin could have an event called Beef-A-Rama and have it become a 61-year tradition.
More than 12,000 people are expected to fill downtown Minocqua Saturday while businesses compete in beef-roasting contests and the aroma of roasting meat fills the streets.
There’s a Beef Eating Contest, Rump Roast Run, live music, kids’ activities, beer gardens and—because apparently beef isn’t enough—a Cow Pie Plop.
Meanwhile, the Prime Choice Art & Craft Show brings more than 100 artists and craftspeople to Torpy Park.
Admission is free and shuttles operate throughout the day.
This one is quintessentially Northwoods Wisconsin. U.S. 51 and Highway 70 both bring you there!
Official Beef-A-Rama information
4. Gays Mills Apple Festival — Gays Mills
September 25–27
Road trip routes: Highways 131 & 171; Highway 60 nearby
The self-proclaimed Apple Capital of Wisconsin celebrates harvest season this weekend.
The Gays Mills Apple Festival spreads throughout town with a carnival, arts and crafts, flea markets, music, dancing, food and Sunday’s big parade.
But don’t just stay downtown.
Some of Wisconsin’s largest apple orchards sit along Highway 171 east of Gays Mills, including century-old orchards overlooking the Kickapoo Valley. This is prime apple-picking, cider-donut and scenic-road-trip territory.
And the surrounding Driftless Area should be just beginning to show hints of fall color. Highway 131 is also a gorgeous drive!
Official Gays Mills Apple Festival information
5. New Glarus Oktoberfest — New Glarus
September 24–27
Road trip routes: Highways 39 & 69
If you’re going to celebrate Oktoberfest in Wisconsin, doing it in America’s Little Switzerland seems like a reasonable choice.
New Glarus Oktoberfest fills downtown with live music throughout the weekend, food, wagon rides and plenty of local beer. The ceremonial keg tapping features Staghorn Octoberfest from New Glarus Brewing Company.
Downtown New Glarus provides a particularly appropriate backdrop, with Swiss architecture, restaurants, shops and plenty more to explore once you leave the festival tent.
Admission is free.
New Glarus Oktoberfest information from Travel Wisconsin
6. Lakeside Oktoberfest — Kenosha
September 24–27
Where: Celebration Place at HarborPark
Road trip routes: I-94, Highways 32, 50 & 158
Kenosha keeps its lakefront festival season rolling with the 5th annual Lakeside Oktoberfest.
Rustic Road Brewing Company hosts four days of craft beer, German-inspired food, live music, contests, charity activities and family fun at Celebration Place overlooking Lake Michigan.
Four days of live music give this Oktoberfest a little broader musical mix than the strictly traditional German variety.
And the HarborPark location means downtown Kenosha, its museums, streetcars and Lake Michigan shoreline are all within easy reach.
Admission is free.
Lakeside Oktoberfest information from Travel Wisconsin
7. 49th Annual Fall Jefferson Car Show & Swap Meet – Jefferson
Friday, September 25 8am-4pm, Saturday, September 26, 6am–4pm
Road trip routes: U.S. 18, Highways 26 & 89
The 49th annual Fall Jefferson Car Show & Swap Meet is back at Jefferson County Fairgrounds this Friday and Saturday! It’s one of the largest car shows in the Midwest, with over 3,100 swap spaces, thousands of car parts and car accessory vendors. It’s one of the best places to buy or sell hard-to-find car parts. The featured vehicle this year will be Camaros, but obviously all makes and models of show vehicles are welcome.
Admission is free, and the Fairgrounds are easily accessible via U.S. 18 or the Highway 26 bypass. Highway 89 brings you close too, and don’t forget the Highway 18 Drive-In is nearby, too!
Jefferson Fall Car Show & Swap Meet Info from Madison Classics
8. Sabor de la Door Hispanic Heritage Festival — Sturgeon Bay
Saturday, September 26, 2–7pm
Where: John Miles County Park
Road trip routes: Highways 42 & 57
Door County celebrates the cultures and traditions of its Hispanic community Saturday with Sabor de la Door.
The festival features live music and cultural performances, traditional foods, family activities and a community soccer kickoff at John Miles County Park in Sturgeon Bay. Admission is free.
It’s also a good starting point for a September drive farther north through Door County on Highways 42 and 57, particularly as the peninsula begins transitioning toward fall color.
Sabor de la Door information from Destination Door County
Aaaand… Weekend Fall Events Coming Soon!
9. Bayfield Apple Festival – Bayfield
October 2-4
Where: venues throughout Bayfield and Bayfield County, Wisconsin
Road trip route: Highway 13
The Bayfield Apple Festival is hailed as one of the 10 Best Fall Harvest Festivals in the nation by USA Today! Bayfield celebrates its Apple Festival every October and in 2026 it will take place October 2nd through the 4th.
The three day event features a farm market featuring local producers, over 60 orchard and food booths selling Bayfield’s apples, apple delicacies, and festival food favorites! There is plenty to buy and see at the 140 art, craft and vendor booths. Kids carnival rides and games, an apple peeling contest, fish fry & dance round out the offerings.
Highway 13 brings you there! More about the Bayfield Apple Festival
10. World Dairy Expo — Madison
September 27–October 2; major exhibits September 29–October 2
Where: Alliant Energy Center
Road trip routes: I-39/90, U.S. 12/18 & U.S. 151
Looking ahead into next week, Madison becomes the center of the dairy world.
World Dairy Expo brings elite dairy cattle, producers, exhibitors and agricultural technology from around the world to the Alliant Energy Center.
The dairy cattle show begins Sunday, September 27, while the huge trade show and educational programming run September 29–October 2. The trade show alone features more than 450 companies from 15 countries, while more than 1,800 dairy cattle exhibitors come to Madison for the cattle competition.
You don’t have to be a dairy farmer to find this fascinating. If you’ve ever wondered what modern Wisconsin agriculture looks like at its highest level—or what some of the world’s finest dairy cattle look like—this is the place to see it.
And really, could there be a more appropriate event for Wisconsin?
World Dairy Expo official site
Pick Some Roads and GO!
This weekend is when Wisconsin’s calendar officially flips from summer festival season to fall festival season.
You can tour cranberry marshes in Warrens, follow the apple orchards through the Driftless Area (and especially Gays Mills), smell and consume roasting beef in Minocqua, hoist a stein in La Crosse, Kenosha, or New Glarus, find or swap rare cars and parts in Jefferson, celebrate Hispanic heritage in Door County— or watch somebody burn a troll outside Mount Horeb.
And next week, people from around the world arrive in Madison for World Dairy Expo and fans of fall and apples head to Bayfield for the annual Bayfield Apple Festival.
The temperatures are getting cooler, harvest season is underway and Wisconsin’s fall colors are starting their annual march south.
Sounds like a pretty good excuse to hit the road.
Pick Some Roads and GO!!
