Looking for Wisconsin festivals and events this weekend and next week? The second half of August is delivering one of the summer’s strongest stretches for Wisconsin road trips. And the weather usually cooperates quite well!
Lake Geneva celebrates summer with Venetian Fest, the Kenosha and Dodge County fairs (among others) fill their fairgrounds, Milwaukee’s lakefront welcomes Mexican Fiesta, Sun Prairie serves up tons—literally—of sweet corn, and Wausau, Green Bay, Superior, Baraboo and Door County all offer very different reasons to hit the road.
Then on Tuesday the 25th, the Central Wisconsin State Fair opens in Marshfield and another round of major festivals gets underway heading into the final weekend of August.
Here are 15 Wisconsin events worth building a road trip around from August 19–30, 2026:
THIS WEEKEND: August 19th–23rd
1. Kenosha County Fair — Wilmot
August 19–23
Road trip routes: I-94, Highways 50 & 83, County Highway W
The Kenosha County Fair returns to Wilmot for five days under the 2026 theme “Fun For The Whole Herd.”
This is the classic Wisconsin county-fair experience: livestock and agricultural exhibits, carnival attractions, food, live entertainment, competitions and grandstand action. Saturday includes the crowning of the 2027 Fairest of the Fair, while Sunday’s traditional fair parade begins at 11 a.m. Races at Wilmot Raceway are featured multiple nights, too!
The fairgrounds sit in western Kenosha County near the Illinois state line near Wilmot, making this one an easy road trip from Milwaukee, Racine, Kenosha, Lake Geneva or northern Illinois. The main way is to follow County W south from Highway 50.
2. Venetian Festival — Lake Geneva
August 19–23
Where: Flat Iron, Library & Seminary Parks
Road trip routes: U.S. 12, Highways 50 & 120
Few Wisconsin festivals have a finale quite like Lake Geneva’s Venetian Festival.
The 64th annual celebration fills downtown with a carnival, live music, food, an arts and crafts fair featuring about 110 artists and crafters, a car and bike show, children’s activities and a Sunday afternoon water-ski show.
Then Sunday evening brings the signature attractions: the Venetian lighted boat parade followed by a huge fireworks display over Geneva Lake. Get a waterfront viewing spot early; this one draws a crowd.
3. Mexican Fiesta — Milwaukee
August 21–23
Where: Henry Maier Festival Park
Road trip routes: I-43, I-794, U.S. 18, Highway 32
Summerfest is long finished, but Milwaukee’s lakefront festival season definitely isn’t. It’s time to Fiesta!
Mexican Fiesta takes over Henry Maier Festival Park for three days celebrating Mexican culture through music, mariachi, dance, traditional foods, cultural exhibits and entertainment. The festival describes itself as a celebration of the “sound, culture and taste of México,” and it has become one of Milwaukee’s signature ethnic festivals.
It’s also an easy event to combine with Milwaukee’s lakefront, Historic Third Ward and downtown attractions.
4. Sun Prairie Sweet Corn Festival — Sun Prairie
August 19–23
Where: Angell Park
Road trip routes: U.S. 151, Highways 19 & 73
How serious is Sun Prairie about sweet corn?
Try 80 tons of Wisconsin-grown corn.
The 73rd annual Sweet Corn Festival begins Wednesday with a downtown parade and block party before shifting to Angell Park for carnival rides, live music, food, children’s activities and plenty of corn. The freshly steamed corn gets served Saturday and Sunday, slathered in butter and sprinkled with however much salt your cardiologist will tolerate.
It’s one of those unmistakably Wisconsin summer traditions—and an easy side trip from Madison.
5. ArtFest Green Bay — Green Bay
August 22–23
Where: Cherry & Jefferson Streets downtown
Road trip routes: I-41, I-43, U.S. 141, Highways 29, 32, 54, 57
Downtown Green Bay becomes an outdoor gallery for ArtFest Green Bay, happening on new August dates this year.
Artists fill Cherry and Jefferson Streets while musical performances, food, demonstrations and hands-on art activities add to the atmosphere. Saturday runs from 9 a.m.–7 p.m. and Sunday from 10 a.m.–4 p.m.
It’s a nice opportunity to explore downtown Green Bay, the CityDeck and Fox River waterfront before or after browsing the artwork.
6. Big Bull Falls Blues Fest — Wausau
August 21–22
Where: Fern Island Park
Road trip routes: I-39/U.S. 51, Highway 29
Wisconsin’s longest-running blues festival celebrates its 35th year on an island in the Wisconsin River right in downtown Wausau.
Big Bull Falls Blues Fest brings two days of live blues to Fern Island Park, with Friday and Saturday performances, food and beverages in a beautiful riverside setting.
The 2026 lineup includes Ally Venable Friday and a Saturday slate featuring Ronnie Baker Brooks, Ana Popovic and the Devon Allman Project, among others.
This is definitely one of the weekend’s stronger choices for music fans.
7. Lake Superior Dragon Boat Festival — Superior
August 21–22
Where: Barker’s Island
Road trip routes: U.S. 2, U.S. 53, Highway 35
Colorful dragon boats race across Superior Bay during one of the Twin Ports area’s most distinctive summer gatherings.
Friday evening includes the Glow By The Bay 5K, food trucks, beverages and live music. Saturday brings the actual dragon-boat racing, with teams competing on a 300-meter course off Barker’s Island. The festival itself is free for spectators.
Add the Lake Superior waterfront and nearby Duluth to the trip and this easily becomes a full Northland weekend.
8. Dodge County Fair — east of Beaver Dam
August 19–23
Road trip routes: U.S. 151, Highway 33
The Dodge County Fair is a particularly good choice for people who like their county fairs with plenty of horsepower.
A Badger State truck and tractor pull starts things Wednesday, with agriculture, fair food, midway attractions and grandstand entertainment continuing through Sunday. Even better, grandstand shows are included with fair admission.
Saturday night’s concert brings George Thorogood & The Destroyers to the fair, adding some serious rock & roll to the cows, corn dogs and tractor pulls.
9. Badger Steam & Gas Engine Club Annual Show — Baraboo
August 21–23
Where: S3347 Sand Road
Road trip routes: U.S. 12, Highways 33 & 136
If giant old machines fascinate you, allow some time for this one.
The 63rd annual Badger Steam & Gas Engine Club Show spreads across a remarkable 293-acre site outside Baraboo with hundreds of operating steam, gas and stationary engines, antique tractors and other vintage machinery.
You’ll also find demonstrations, sawmills, a flea market and plenty of reminders of just how much mechanical muscle it once took to run farms and industries.
Adults are $10, children 12 and younger are free, and Sunday admission is free for veterans.
10. Peninsula Music Festival Finale — Fish Creek
August 20 & 22
Where: Door Community Auditorium
Road trip route: Highway 42
For a considerably different kind of musical road trip, the Peninsula Music Festival concludes its 74th season in Door County this weekend.
Thursday’s program is Revolution and Romance, followed Saturday by the season finale, Mahler’s Third: A World in Symphony. The festival brings together an international professional symphony orchestra under Music Director Rune Bergmann.
Combine the concert with a Highway 42 drive through Egg Harbor and Fish Creek and you’ve got a pretty impressive Door County summer evening!
COMING UP: AUGUST 25–30
11. Central Wisconsin State Fair — Marshfield
August 25–30
Where: Marshfield Fairgrounds Park
Road trip routes: U.S. 10, Highways 13 & 97
Marshfield takes center stage next week as the Central Wisconsin State Fair begins a six-day run Tuesday.
The 2026 entertainment schedule is especially strong: Hairball performs Wednesday, Home Free Thursday, country star Chris Young Friday and Blackberry Smoke Saturday. Sunday’s grandstand event is the Challenge of Champions bull-riding competition.
The fair also brings the traditional mix of midway attractions, exhibits, food and agricultural activities to the grounds. One new planning note for 2026: a clear-bag policy applies to grandstand events.
12. Great River Folk Festival — La Crosse
August 28–30
Where: Riverside Park
Road trip routes: I-90, U.S. 14/61, Highway 35
The Great River Folk Festival celebrates its 50th anniversary this year, which makes 2026 an especially good time to experience it.
Since 1976, the festival has brought music, dance, visual art, crafts and other folk traditions to beautiful Riverside Park along the Mississippi River. Artists arrive from around the Midwest and across the country for three days of performances in a relaxed setting.
And because this is La Crosse, the river, downtown and surrounding Driftless bluffs are all waiting once the music ends.
13. Clearwater Jazz & Art Festival — Eau Claire
August 28–29
Where: The Brewing Projekt
Road trip routes: I-94, U.S. 12, U.S. 53, Highways 37 & 93
Jazz, visual art, craft beverages and food trucks come together at the Clearwater Jazz & Art Festival in Eau Claire.
Friday evening features Take That Back with Joan Hutton and Sue Orfield, while Saturday offers nonstop jazz across three stages plus a fine-art fair. The entire event is free and all-ages.
That’s a pretty attractive price for a late-August musical road trip.
14. Orton Park Festival — Madison
August 28–30
Where: Orton Park
Road trip routes: I-39/90, U.S. 12/18, U.S. 151, Highway 113
Madison’s original East Side music festival returns for its 61st year beneath the massive oak trees of historic Orton Park.
The free weekend combines local and touring bands, food and neighborhood festival atmosphere with spectacular performances by Cycropia Aerial Dance, whose performers take to the trees above the park Friday and Saturday nights.
It’s one of Madison’s more distinctive summer traditions and a nice excuse to explore the city’s near-east-side neighborhoods.
15. Pistons & Props Airshow — Janesville
August 28–30
Where: Southern Wisconsin Regional Airport
Road trip routes: I-39/90, U.S. 14, U.S. 51, Highway 11, Highway 26
Here’s something brand new for the Wisconsin event calendar:
The Pistons & Props Airshow launches its inaugural weekend at Southern Wisconsin Regional Airport with airplanes, cars, motorcycles, hot air balloons and plenty happening both on the ground and overhead.
Friday’s Veterans Night includes aircraft rides, motorcycles, live music, balloons and fireworks. Saturday adds a car show and airshow, while another full airshow takes place Sunday. Both weekend airshows begin with a pre-show around 12:30 p.m., followed by flying performances beginning at 1 p.m.
For aviation buffs—or anyone who just likes watching loud things go very fast—this could become a pretty significant new Wisconsin summer event!
The nice thing about this stretch of August is the variety.
You can watch fireworks reflected across Geneva Lake, eat your weight in sweet corn, hear blues on an island in Wausau, watch dragon boats race on Lake Superior, wander through a county fair, see steam engines come back to life near Baraboo or settle into a symphony concert in Door County.
Then do it all over again next weekend with the Central Wisconsin State Fair, folk and jazz festivals, aerial dancers and an airshow.
Pick an event. Find an interesting Wisconsin highway that gets you there. And don’t be afraid to make a few unexpected stops along the way.
