October has arrived in Wisconsin—and apparently it brought cranberries, apples, pumpkins, lederhosen and dragons with it.
This weekend you can tour working cranberry marshes near Eagle River, imbibe in apples and plenty of events in Bayfield, watch giant pumpkins get dropped in Nekoosa, celebrate Oktoberfest among Cedarburg’s historic buildings, explore the birthplace of Dungeons & Dragons in Lake Geneva or head north to Stone Lake for another massive celebration of Wisconsin’s cranberry harvest.
Throw in fall celebrations in Wausau and Kenosha, hundreds of craft beverages in Green Bay, a big fall racing event at Road America, and one of northwestern Wisconsin’s classic harvest festivals, and there’s no shortage of excuses to hit the road.
Here are 12 Wisconsin festivals and events worth a road trip this first weekend of October!
1. Cranberry Fest — Eagle River
October 3–4; cranberry marsh tours October 1–4
Where: Vilas County Fairgrounds & downtown Eagle River
Road trip routes: U.S. 45, Highways 17 & 70
Few things say Wisconsin in October quite like cranberry harvest season.
Eagle River Cranberry Fest fills the Vilas County Fairgrounds and downtown with fresh cranberries and craisins, cranberry foods and drinks, handmade arts and crafts, an antique and vintage market, farmers market and family entertainment.
The festival runs 9am–4pm Saturday and 9am–3pm Sunday, with free shuttles connecting festival locations Saturday.
But one of the coolest parts starts before the festival itself. Cranberry marsh tours run October 1–4, taking visitors to Lake Nokomis to see a working cranberry harvest—including those photogenic flooded beds filled with floating red berries. Tours are $10 for adults and $5 for children ages 6–12; reservations are strongly recommended.
Add in Northwoods fall color and you’ve got one heck of an October road trip.
2. Bayfield Apple Festival — Bayfield
Now through Sunday, October 4
Road trip routes: 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.
You can also catch Big Top Chautauqua’s Blue Canvas Orchestra perform throughout the weekend on the Grandstand stage. The festival culminates with the Grand Parade on Sunday, which features a 400 member “Mass Band” finale.
Bayfield is located along Highway 13 on the shores of Lake Superior, about 15 minutes north of U.S. 2. U.S. 63 brings you towards Bayfield from the Hayward, Spooner, and Twin Cities areas; U.S. 51 north through the North Woods sends you toward U.S. 2 for the connection to Bayfield, too. Enjoy the fall colors on your ride!
Bayfield Applefest info and schedule
3. Stone Lake Cranberry Festival — Stone Lake
Saturday, October 3, 9am–5pm
Road trip routes: U.S. 63, Highways 27 & 70
Apparently one giant Wisconsin cranberry festival isn’t enough for one weekend.
The 48th annual Stone Lake Cranberry Festival brings thousands of visitors to this little northwestern Wisconsin community for one very busy Saturday.
More than 300 vendors fill town with arts, crafts and food, while fresh Wisconsin cranberries and craisins are sold by the thousands of pounds. There’s also a parade, live entertainment, cranberry-themed foods and the delightfully named Cranberry Krate Derby.
Stone Lake sits between Spooner and Hayward, making this an excellent destination for a Northwoods fall-color drive.
And yes—the festival goes on rain, shine or snow.
Because Wisconsin. And the forecast actually looks pretty nice.
Stone Lake Cranberry Festival schedule
4. Cedarburg Oktoberfest — Cedarburg
October 3–4
Road trip routes: I-43 & Highway 60
Cedarburg just finished celebrating wine and the harvest. Now it’s time for beer, brats and lederhosen.
Cedarburg Oktoberfest fills the Community Center grounds and nearby City Hall lawn with German music, dancers, food and plenty of Oktoberfest beer. Saturday runs 10am–8pm and Sunday 10am–5pm, with free admission.
Look for German dancing, the wonderfully goofy Glockenspiel Show every two hours and contests involving stein holding, pretzel eating, braids and the best lederhosen and dirndls.
Foxtown Brewing hosts a biergarten on the City Hall lawn, while an expanded marketplace offers bratwurst, German dinners and other treats.
Then take some time to wander Washington Avenue and Cedarburg’s collection of more than 100 historic buildings.
Prost!
Cedarburg Oktoberfest information from Travel Wisconsin
5. Nekoosa GIANT Pumpkin Fest — Nekoosa
October 3–4
Road trip routes: Highways 13, 54 & 73
How giant is GIANT?
Nekoosa intends to find out.
The Nekoosa Giant Pumpkin Fest brings enormous pumpkins and a full slate of appropriately pumpkin-related activities to the community Saturday and Sunday.
There’s a giant pumpkin weigh-off, pumpkin pie-eating contest, pumpkin rolling, decorating, carnival activities and—because merely weighing gigantic pumpkins apparently isn’t dramatic enough—a giant pumpkin drop.
Hours are 9am–5pm Saturday and 9am–4pm Sunday.
Admission is $4 for adults, $1 for ages 4–7 and free for children 3 and younger.
If you’ve ever wondered just how ridiculously large somebody can grow a pumpkin, here’s your opportunity.
Nekoosa Giant Pumpkin Fest information from Travel Wisconsin
6. Dragon Days Fantasy Festival — Lake Geneva
October 3–4, 10am–5pm
Road trip routes: U.S. 12, Highways 50 & 120
Lake Geneva has resorts, mansions, beaches—and an important place in fantasy gaming history.
The city was home to Gary Gygax, co-creator of Dungeons & Dragons, and the company TSR that originally published the game. Dragon Days Fantasy Festival celebrates that legacy throughout downtown Lake Geneva.
Activities spread across Library Park, Geneva Lake Museum, the Geneva Theater, Lake Geneva Public Library, Horticultural Hall and 330 Center Street—the birthplace of D&D.
The city-wide festival is designed for fantasy fans, gamers and families, with one-day and weekend admission available; children 12 and younger are free.
For Wisconsin road-trip enthusiasts who like roadside history that’s a little different, Lake Geneva’s role in launching the modern fantasy-gaming phenomenon is quite a story. U.S. 12, Highway 50, and Highway 120 bring you to Lake Geneva for all the fun!
Dragon Days information from Visit Lake Geneva
7. Mission Foods SCCA National Championship Runoffs at Road America – Elkhart Lake
Thursday, October 1 – Sunday, October 4
Where: Road America, Elkhart Lake, WI
Road trip routes: Highway 67
The Sports Car Club of America™ (SCCA®) has crowned road racing’s best amateur competitors from across North America for more than six decades at a winner-take-all National Championship race. The tradition continues for a 63rd time now through Sunday, October 4th at America’s National Park of Speed during the 2026 Mission Foods SCCA National Championship Runoffs®.
Tucked amongst rolling Kettle Moraine hills between Plymouth and Elkhart Lake right along Highway 67, Road America hosts the Summit Racing Equipment SCCA Road Racing program’s ultimate gathering for a third straight year. It’s a legendary event at a wonderous 4.048-mile, 14-turn circuit that never disappoints!
Road America’s Mission Foods SCCA National Championship Runoffs info
8. Harvest Fest — Wausau
Saturday, October 3
Where: The 400 Block, downtown Wausau
Road trip routes: I-39/U.S. 51, Highways 29 & 52
Downtown Wausau welcomes October with Harvest Fest on the 400 Block.
The annual celebration combines local vendors, crafts, live music, seasonal treats, pumpkin picking and family activities in the heart of downtown.
The location makes this an easy addition to a larger central Wisconsin fall-color road trip. Rib Mountain, the Wisconsin River and downtown Wausau are all right there, while Highways 29 and 52 provide plenty of options for exploring farther east or west.
Wausau Harvest Fest information
9. Craftoberfest — Green Bay
Saturday, October 3, 3–6pm
Where: Resch Expo
Road trip routes: I-41, I-43, Highways 29, 32 & 172
Green Bay takes the word Oktoberfest and adds a whole lot of craft beverages.
Craftoberfest returns to Resch Expo as one of the region’s largest beverage-sampling events, offering unlimited samples from hundreds of craft beverages, including beer, wine, spirits and more.
General admission runs from 3–6pm, with upgraded ticket options offering earlier access and additional tastings.
This one is strictly 21+, including designated drivers, and every attendee receives a sampling glass.
And yes, you’re basically next door to Lambeau Field, so Green Bay offers plenty of opportunities to expand the road trip.
Craftoberfest official information from Discover Green Bay
10. Flannel Fest — Kenosha
Saturday, October 3
Where: Petrifying Springs Biergarten
Road trip routes: I-94, Highways 31, 32 & 50
It’s October in Wisconsin.
Time to break out the flannel.
Flannel Fest returns to Petrifying Springs Biergarten in Kenosha County with food trucks, live music, children’s activities, competitions and plenty of fall atmosphere.
The setting is part of the attraction. Petrifying Springs Park—or “Pets,” as generations of locals have called it—offers wooded trails, picnic areas and plenty of room for a fall walk before or after the festival.
And by early October, the trees should be starting to cooperate with the whole flannel theme.
Flannel Fest information from Visit Kenosha
11. Thorp Pumpkin Festival — Thorp
Saturday, October 3, 9am–4pm
Road trip routes: Highway 29 & Highway 73
Pumpkins take over downtown Thorp Saturday during the annual Thorp Pumpkin Festival.
More than 130 arts, crafts and food booths line the festival area along with live music, a petting zoo and family activities.
Naturally, pumpkins take center stage. Look for pumpkin painting and carving contests along with The Great Pumpkin Weigh-In.
Admission is free.
Thorp sits right along Highway 29 between Wausau and Eau Claire, making Pumpkin Fest an easy stop during a central Wisconsin fall-color drive.
Thorp Pumpkin Festival information from Travel Wisconsin
12. Phillips Fall Harvest Festival — Phillips
Saturday, October 3, 9am–3pm
Road trip routes: Highway 13 & Highway 111
If you’re looking for an excuse to head deeper into Wisconsin’s Northwoods during fall-color season, Phillips provides one.
The Phillips Fall Harvest Festival fills downtown with an arts and crafts fair, fall produce, food, music and children’s activities.
And since this is cranberry country, the festival’s signature product is locally grown fresh cranberries and craisins, available from the Phillips Area Chamber of Commerce.
Admission is free.
Highway 13 through Price County should also provide some excellent scenery on the way there, especially as northern Wisconsin moves toward peak fall color.
Phillips Fall Harvest Festival information from Travel Wisconsin
Pick Some Roads and GO!
This weekend offers a pretty convincing argument for heading north.
Wisconsin’s cranberry harvest is underway, and both Eagle River and Stone Lake turn it into major celebrations. Phillips adds another taste of cranberry country, while the Northwoods should be putting on an increasingly impressive fall-color show.
But there’s plenty happening farther south, too.
You can celebrate Oktoberfest among Cedarburg’s historic buildings, watch giant pumpkins fall from the sky in Nekoosa, celebrate Wisconsin’s role in the birth of Dungeons & Dragons in Lake Geneva, sample hundreds of craft beverages in Green Bay or simply throw on some flannel and head for Kenosha.
October is here.
The harvest is underway.
The leaves are changing.
Sounds like road-trip season to us.
Pick Some Roads and GO!!
