MidwestWeekends.com — Your Travel Guide to the Upper Midwest

So many festivals, so little fall

The season is short, so go on a power trip and catch two or three festivals each weekend. Here's where to go.

Pumpkin regatta in Cedarburg.

© Cedarburg CVB

In Cedarburg, paddlers race hollowed-out pumpkins across Cedar Creek.

In this part of the world, fall is sweet but way too short.

All of the quaint little towns along rivers and in the bluffs have to pack their autumn festivals into the same six weekends, rolling out parades, pumpkin contests and oompah bands for all the leaf-peeping tourists.

The choices are paralyzing. Flea market or scarecrow contest? Pumpkin regatta or studio tour? Yodeling contest or dachshund races?

You can't do it all, but you can do a lot. Just go on a power trip to two, even three festivals in one weekend.

If you want to cram in as many fall festivities as possible before cold weather arrives, here's a guide to the best place to be each weekend in 2019.

For more festivals, see our Events Calendar and our lists of Oktoberfests, grape stomps and art-studio tours in Minnesota, Wisconsin, Iowa, northern Illinois and western Michigan.

If you want to stay overnight, make reservations as soon as possible. And before setting out, call or check websites for festival highlights and plan around them.

Weekend after Labor Day: Southern Minnesota and the Twin Cities

The first time I went power tripping was the weekend after Labor Day, when Northfield holds its Defeat of Jesse James Days, the historic village of Mantorville holds Marigold Days and the Minnesota River college town of St. Peter holds the Rock Bend Folk Festival.

Decorated pumpkins at Wisconsin Dells.

© Beth Gauper

At many fall festivals, kids get to decorate pumpkins.

Don't miss the bank-raid re-enactments in Northfield, where the bad guys ride horses. In Mantorville, catch a melodrama. In St. Peter, kick back in the city park and listen to as much music as you want it's free.

I hit them all on a day trip from the Twin Cities, and after three festivals and three towns, I felt as if Id been gone three days. The best thing was that fall was just getting started.

Side trip: Just west of Minneapolis on Lake Minnetonka, James J. Hill Days in Wayzata is known for its dachshund races. Also in the Twin Cities: the zany Flugtag in St. Paul and the down-home Monarch Festival on Lake Nokomis in Minneapolis.

Second weekend of September: Michigan side of Lake Michigan

Hang onto summer with a trip to the balmy shores of Lake Michigan. On the Michigan side, the Michigan Irish Music Festival in the port town of Muskegon includes Highland Games as well as music and dancing.

In nearby Grand Haven,  the Salmon Festival celebrates the annual migration of salmon as well as leaf peepers.

If you want to keep going along the Michigan shore and the Circle Tour of Lake Michigan is one of our favorite trips the free South Haven Jazz Festival is held in South Haven along the harbor.

Third weekend of September, Wisconsin side of Lake Michigan

On the other side of Lake Michigan, start near the Illinois border in Racine, for the Party on the Pavement street festival.

Along the lake in Milwaukee, the Bay View neighborhood celebrates its Bay View Bash, and north of town in Glendale, stop by the monthlong Oktoberfest at the Bavarian Bierhaus on Heidelberg Park.

It includes folk dancing, sing-alongs, yodeling and such typical German festival foods as spanferkel and rollbraten.

Jesse James reenactment in Northfield.

© Beth Gauper

Northfield reenacts an infamous raid during Defeat of Jesse James Days.

Then drive or bike, using Ozaukee County's Interurban Trail to the historic Yankee mill town of Cedarburg for Wine & Harvest Festival.

Don't miss the Great Pumpkin Regatta, where paddlers in hollowed-out pumpkins race across Cedar Creek, or the grape stomp.

The bicycle trail ends at the county line, north of Belgium. But if you keep going, you'll hit Two Rivers and its Ethnic Festival on Saturday.

Even farther north, at the gateway to the Door Peninsula, Sturgeon Bay holds its Harvest Fest and Street Art Auction

Fourth weekend of September: St. Croix and Mississippi river valleys

In fall, the small towns that line the St. Croix and Mississippi between Minnesota, Wisconsin and Iowa are favorite destinations. This weekend is a particularly good time to go.

Just east of the Twin Cities on the St. Croix, the village of Afton holds Afton Art in the Park. After that, head south on St. Croix Trail, where apple orchards will be offering hay rides and trips through corn mazes.

And across the river in Lakefront Park, Hudson holds Spirit of the St. Croix Art Festival, with a juried show, music and food.

The Mississippi is like a magnet in the fall. In La Crosse, the big Oktoberfest parade is at 10 a.m. Saturday.

The most scenic part of the Upper Mississippi may be northeast Iowa. Drive up to Effigy Mounds National Monument to hike along the bluffs.

A hop farther in McGregor, a quirky little town tucked at the foot of the bluffs,  see a Hole in the Sock Gang street shootout on Saturday.

Take time to drive up to Pikes Peak State Park, 500 feet above the river. The views are spectacular, and admission is free.

A float from the La Crosse Oktoberfest parade.

© Beth Gauper

The La Crosse Oktoberfest crew whoops it up during the parade.

There are more views on the drive to Dubuque. Just across the river, Galena, Ill., is holding its annual Tour of Historic Homes, and Galena Cellars its Fall Harvest Festival.

First weekend of October: Southeast Iowa and northwest Illinois

In southeast Iowa, you can go to three fall festivals just half an hour from each other: Northside Oktoberfest and Iowa City Book Festival in Iowa City and Oktoberfest in Amana.

In northwest Illinois, head for Oregon on the Rock River, where you'll find the Olde English Faire and Autumn on Parade. In Galena, there's Oktoberfest.

Sidetrip: Enjoy both a big-town Oktoberfest in Milwaukee and a small-town Oktoberfest in Cedarburg, a historic mill town just to the north.

Second weekend of October: Driftless Area of Wisconsin, Iowa and Illinois

The glaciers slid around this area, leaving a lumpy quilt of hills, ridges and coulees. 

Dachshund races at a festival.

© Beth Gauper

James J. Hill Days features a dachshund dash.

Just east of La Crosse, Norskedalen will hold its dramatic Civil War Immersion weekend in Coon Valley

Around ReedsburgFermentation Fest includes programs on making beer, cheese, bread and other fermented favorites.

Across the border in the bluffs of northeast Iowa, visit 51 artists at 37 studios in and around Decorah on the Northeast Iowa Artists' Studio Tour.

In the northwest corner of Illinois, Galena is holding its Galena Country Fair in Grant Park, which includes a big bake sale, farmers market and arts show. 

Farther south on the Illinois River, near Starved Rock State ParkUtica is holding its Burgoo Festival

Half an hour farther west in Princeton, Civil War re-enactors stage battles at the Shadows of the Blue and Gray historical festival.

Third weekend of October: Southeast Wisconsin

You can catch the season's last Oktoberfest in Elkhorn, not far from Lake Geneva. 

Just to the east, near Racine, Union Grove gets out the catapults for its Pumpkin Chuckin Fest. At dusk, drive over to Eagle and Old World Wisconsin for Halloween Legends and Lore.

Southwest Wisconsin also makes a good destination. The popular Fall Art Tour winds through picturesque nooks and crannies in and around the towns of Baraboo, Dodgeville, Mineral Point and Spring Green.

While you're there, take an hour or two to hike in Devil's Lake State Park just south of Baraboo, which often has good fall color this weekend.

And in nearby Wisconsin Dells, head downtown for the beer-tasting blowout Dells on Tap.

Last updated on September 3, 2019