We’re hitting the heart of October in Wisconsin, and this may be one of the best road-trip weekends of the fall.
Lake Geneva breaks out the beer and brats for Oktoberfest. Pumpkins take over Egg Harbor in Door County. More than 170 artists and crafters fill downtown Baraboo. Two Rivers celebrates Wisconsin’s apple harvest. Spooner rolls pumpkins through downtown. And two separate self-guided art tours give you an excuse to explore Wisconsin’s fall colors while traveling from studio to studio.
There’s wine in Racine, giant pumpkins in Fond du Lac, scarecrows along Lake Michigan and plenty more.
Here are 14 Wisconsin festivals and events worth building a road trip around October 9–11, 2026.
1. Lake Geneva Oktoberfest — Lake Geneva
October 10–11
Where: Downtown Lake Geneva
Road trip routes: U.S. 12, Highways 50 & 120
Lake Geneva combines Oktoberfest with one of southern Wisconsin’s best fall road-trip destinations this weekend.
The annual Lake Geneva Oktoberfest brings German-inspired food, craft beer, a beer garden, live entertainment, local vendors, children’s activities and the always-entertaining dachshund races downtown.
Admission is free!
And Oktoberfest is really only part of the attraction. Take a walk along Geneva Lake, explore downtown, or follow Highway 50 around the lake toward Williams Bay and Fontana while the fall colors are putting on their annual show.
Beer, brats, a beautiful lake and October color?
Prost!
Lake Geneva Oktoberfest information from Visit Lake Geneva
2. Pumpkin Patch Festival — Egg Harbor
October 10–11, starting at 9am
Where: Downtown Egg Harbor
Road trip routes: Highways 42 & 57
Door County in October is already a pretty convincing road-trip destination. Add Pumpkin Patch Festival, and you’ve got even more reason to head up the peninsula.
Egg Harbor’s largest annual event fills downtown with live music, carnival rides, arts and crafts vendors, pumpkin and scarecrow displays, face painting, children’s activities, a roaming magician, raffles and plenty of food. Admission is free.
Of course, getting there is half the fun. Highway 42 follows the Green Bay side of the Door Peninsula through Sturgeon Bay, Carlsville and Egg Harbor, while Highway 57 provides another scenic option up the peninsula.
October color + Door County + pumpkins?
Sounds like a road trip to us.
Pumpkin Patch Festival from Destination Door County
3. Fall Fair on the Square — Baraboo
Saturday, October 10, 9am–4pm
Where: Downtown Baraboo
Road trip routes: U.S. 12, Highways 33 & 136
Downtown Baraboo’s historic courthouse square fills with more than 170 artists and crafters for the annual Fall Fair on the Square.
Add food, live entertainment, downtown shops and the surrounding fall colors and you’ve got a pretty easy Saturday road trip.
And don’t necessarily head straight home afterward. Devil’s Lake State Park is minutes away, the Wisconsin Dells are just up U.S. 12 and the Baraboo Hills should be looking increasingly spectacular in mid-October.
4. Fall Wine Walk — Racine
Saturdays, October 10 & 17, 1–6pm
Where: Downtown Racine
Road trip routes: I-94, Highways 11, 20, 32 & 38
Why settle for one Saturday when you can have two?
The Downtown Racine Fall Wine Walk takes place on consecutive Saturdays, October 10 and October 17, offering visitors a chance to sip, stroll, shop and explore downtown.
The route includes 30 participating businesses, with 20 wine samples plus 10 beer, cider and seltzer samples and snacks along the way. A $40 general-admission ticket includes the tastings, a sampling glass and canvas tote.
That also makes this one worth mentioning again in next week’s roundup for anyone who can’t make it this Saturday.
Downtown Racine’s architecture, shops, restaurants and Lake Michigan waterfront provide plenty of reasons to make an afternoon of it.
Downtown Racine Fall Wine Walk information
5. Applefest — Two Rivers
Saturday, October 10, 9am–3pm
Where: Central Park and downtown Two Rivers
Road trip routes: Highways 42, 147 & 310; I-43 nearby
Two Rivers celebrates one of fall’s tastiest crops during the 42nd annual Applefest.
Central Park and the surrounding downtown fill with apple growers, fresh apples, baked goods, arts and crafts, activities and live entertainment throughout the day. The Sugar Bush Boys perform from 9am–noon, followed by 5 Card Studs from 12:30–3pm.
While you’re downtown, wander a few blocks and check out Cool City Brewing, Two Rivers’ downtown brewpub. It’s a natural place to extend the visit with a locally brewed beer after Applefest—and another excuse to explore the city’s historic downtown.
Then follow Highway 42 toward Lake Michigan, check out the harbor and perhaps continue toward Point Beach State Forest.
Apples + craft beer + Lake Michigan makes for a pretty solid October Saturday.
Official Two Rivers Applefest site
6. Jack-O-Lantern Festival — Spooner
October 9–10
Where: Downtown Spooner
Road trip routes: U.S. 63, Highways 70 & 253
Spooner is going all-in on pumpkins this weekend.
The Jack-O-Lantern Festival begins Friday afternoon with food trucks and an adult Glow & Go Bar Crawl through participating Spooner establishments.
Saturday shifts into family-festival mode with the 1K Pumpkin Run and 5K Zombie Run/Walk, pumpkin carving, scarecrow and fall-flavor contests, a Kids Zone and the wonderfully Wisconsin-sounding Great Pumpkin Roll.
Most of the festival is free.
Spooner’s location at U.S. 63 and Highway 70 also makes it a natural launching point for exploring northwestern Wisconsin during peak fall-color season.
Official Spooner Jack-O-Lantern Festival information
7. North Woods Art Tour — Wisconsin Northwoods
October 9–11, 10am–5pm
Boulder Junction and surrounding Northwoods communities
Road trip routes: Highways 47, 51, 70 & 155 and plenty of back roads
Here’s another event that seems tailor-made for State Trunk Tour.
The North Woods Art Tour isn’t confined to a festival ground. Instead, visitors create their own road trip among 33 artist studios scattered throughout Wisconsin’s Northwoods.
Artists open their workspaces from 10am–5pm Friday through Sunday, allowing visitors to meet them, watch demonstrations and explore paintings, sculpture, pottery, fiber arts, jewelry and other works.
Boulder Junction provides a terrific base for exploring the tour, particularly with Northwoods fall colors providing the backdrop.
There are no admission fees or tickets.
Grab the map.
Pick some studios.
And Pick Some Roads and GO!!
Official North Woods Art Tour map and information
8. Scarecrow Festival — Sheboygan
October 10–11, 9am–4pm
Where: The Christopher Farm & Gardens
Road trip routes: I-43, Highways 23 & 42
Here’s an opportunity to visit a spectacular Lake Michigan property that isn’t normally just sitting wide open for casual wandering.
The annual Camp Y-Koda Scarecrow Festival takes place at the 500-acre Christopher Farm & Gardens, which includes approximately a mile of Lake Michigan shoreline.
Scarecrows created by businesses, schools, nonprofits, artists and families are displayed throughout the grounds, along with arts and crafts, family activities, train rides and other attractions.
Advance tickets are a good idea because attendance can reach capacity.
9. Covered Bridge Art Studio Tour — Ozaukee & Washington Counties
October 9–11, 10am–5pm
Road trip routes: I-43, Highways 32, 33, 57, 60 & 167
If the North Woods Art Tour isn’t enough, southeastern Wisconsin has its own studio-hopping road trip this weekend.
The Covered Bridge Art Studio Tour sends visitors through Mequon, Thiensville, Cedarburg, Grafton, Saukville, Port Washington and Newburg, visiting artists in their own studios.
There are no tickets or reservations. Just grab the map, watch for the tour signs and create your own route.
You’ll encounter farms, rivers, small towns, Lake Michigan shoreline and plenty of fall color along the way.
This isn’t merely an event.
It’s literally a road trip.
10. Fondy FallToberFest & Wisconsin Great Pumpkin Weigh-Off — Fond du Lac
Saturday, October 10
Where: Lakeside Park
Road trip routes: I-41, U.S. 45, Highways 23 & 151
Oktoberfest meets gigantic vegetables in Fond du Lac.
Fondy FallToberFest combines Wisconsin’s enthusiasm for autumn and German festivities with the Wisconsin Great Pumpkin Weigh-Off at Lakeside Park.
Look for enormous pumpkins, pumpkin launching, horse-drawn wagon rides, live music, food trucks and Oktoberfest traditions—all along Lake Winnebago.
And yes, the pumpkins can get genuinely enormous.
11. Autumn Celebration Weekend — Greenbush
October 10–11
Where: Wade House Historic Site
Road trip routes: Highway 23; Highway 67 nearby
Travel back to a Wisconsin autumn of the 1800s at Wade House Historic Site.
Autumn Celebration Weekend includes pumpkin carving, apple pressing, seasonal games, hot apple cider and horse-drawn carriage rides around the historic property.
It’s an especially appropriate State Trunk Tour stop because Wade House sits right along Highway 23 between Sheboygan and Fond du Lac beside the Kettle Moraine State Forest.
Combine this with Fond du Lac’s FallToberFest or Sheboygan’s Scarecrow Festival for a full Highway 23 road trip.
12. Crex Meadows Fall Festival — Grantsburg
Saturday, October 10
Road trip routes: Highways 35, 48 & 70
Fall isn’t just about pumpkins, apples and Oktoberfest.
At Crex Meadows Wildlife Area, it’s also about sandhill cranes.
The annual Fall Festival offers crane-viewing opportunities, wildlife programs and activities at one of Wisconsin’s premier wildlife areas.
Crex Meadows encompasses thousands of acres of wetlands, prairie and forest near Grantsburg, making the journey worthwhile even without a festival.
Bring the binoculars.
13. Norskedalen Civil War Experience — Coon Valley
October 10–11
Road trip routes: U.S. 14/61, Highways 33 & 162
The Driftless Area goes back to the 1860s this weekend.
During the Civil War Experience at Norskedalen, re-enactors transform the heritage center grounds into a living-history encampment.
Visitors can watch military drills, demonstrations and recreated battle skirmishes while learning about both military and civilian life during the Civil War.
Norskedalen’s wooded setting outside Coon Valley should also be particularly impressive with October color spreading through the Driftless Region.
14. Swiss Historical Village Harvest Fest — New Glarus
Sunday, October 11
Road trip routes: Highways 39 & 69
Finish the weekend with a little Swiss Wisconsin history.
The Swiss Historical Village Harvest Fest recreates traditional skills and daily life with cheesemaking, blacksmithing, spinning, basket weaving and Swiss brätzeli cookie demonstrations.
You’ll also find historical interpreters and traditional Swiss entertainment—including yodeling and alphorns.
And because you’re in New Glarus, the Swiss experience certainly doesn’t end when you leave the festival grounds.
Pick Some Roads and GO!
If you’re looking for a weekend when the drive itself is every bit as important as the destination, this is it.
Follow Highway 50 into Lake Geneva for Oktoberfest. Take Highways 42 and 57 into Door County for Pumpkin Patch. Follow Highway 42 along Lake Michigan toward Two Rivers for Applefest. Explore Highway 70 through northern Wisconsin on the way to Spooner—or spend an entire weekend hopping between artist studios around Boulder Junction.
Closer to Lake Michigan, sip your way around downtown Racine, explore artists’ studios around Cedarburg and Port Washington or wander among scarecrows on a 500-acre estate near Sheboygan.
The leaves are turning.
The apples are ripe.
The pumpkins are enormous.
And Wisconsin’s roads are waiting.
