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.

Jesse James reenactment in Northfield.

© Beth Gauper

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

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 2018.

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

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.

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.

Pumpkin regatta in Cedarburg.

© Cedarburg CVB

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

Side trip: Just west of Minneapolis on Lake Minnetonka, James J. Hill Days in Wayzata is known for its dachshund races.

Third weekend of September: Lake Michigan, both sides

Hang onto summer with a trip to the balmy shores of Lake Michigan. On the Michigan side, start in Grand Haven with the Salmon Festival, which celebrates the annual migration of salmon as well as leaf peepers.

Just up the shore, the Michigan Irish Music Festival in the port town of Muskegon includes Highland Games as well as music and dancing.

If you want to keep going along the Michigan shore and the Circle Tour of Lake Michigan is one of our favorite trips there's a Hops and Props craft beer and wooden-boat show on Saturday in Manistee.

On the Wisconsin side of Lake Michigan, start in Glendale, on the northern edge of Milwaukee

The monthlong Oktoberfest at the Bavarian Bierhaus on Heidelberg Park is the oldest in the Midwest. It includes folk dancing, sing-alongs, yodeling and such typical German festival foods as spanferkel and rollbraten.

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.

Fourth weekend of September: St. Croix River Valley of Minnesota and Wisconsin

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

Scarecrows in a contest.

© Beth Gauper

In northern Illinois, St. Charles holds Scarecrow Fest.

In Interstate State Park in Taylors Falls, there's a guided bluffs hike Saturday and a glacial pothole tour Sunday. Across the river in St. Croix Falls, Chateau St. Croix is holding a free Harvest Festival.

Sample wine or win a prize at two grape-stomp festivals, one at in St. Croix Falls at Dancing Dragonfly Winery and one down the river in downtown Stillwater, at Northern Vineyards.

Farther down the river, 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.

Fifth weekend of September: Mississippi River Valley and southeast Iowa

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.

Down at the riverside, it's the first of two weekend Flea Markets Under the Bridge in Marquette. A hop farther, see a Hole in the Sock Gang street shootout Saturday in McGregor, a quirky little town tucked at the foot of the bluffs.

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

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.

And in southeast Iowa, you can go to two fall festivals just half an hour from each other: Northside Oktoberfest in Iowa City on Saturday and Fall Festival Friday and Saturday in Kalona.

First weekend of October: Wisconsin's Door Peninsula and northern Illinois

Decorated pumpkins at Wisconsin Dells.

© Beth Gauper

Kids decorated pumpkins at Autumn Harvest Fest in the Dells.

With all its orchards, Door County is impossibly scenic in fall, and its fall color tends to hang on longer than most places.

Head up the Door Peninsula for the Pumpkin Patch Festival in Egg Harbor and the Townline Art Fair in Ephraim.

Another good option: northern Illinois. Heading west from Chicago, swing by St. Charles for Scarecrow Fest, and head for Oregon on the Rock River, where you'll find the Olde English Faire and Autumn on Parade.

In the northwest corner of the state, 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 Park, Utica is holding its Burgoo Festival

Second weekend of October: Driftless Area of Wisconsin and Iowa

In the Wisconsin Dells, head downtown for the beer-tasting blowout Dells on Tap.

Pop-up art along the Farm/Art DTour.

© Debra Gagner

There's pop-up art and performances along the scenic Farm/Art DTour.

To the south, in the hills around Reedsburg, Fermentation Fest includes programs on making beer, cheese, bread and other fermented favorites, as well as the popular Farm/Art DTour, with art and pop-up performances along a scenic, 50-mile route.

To the west, Norskedalen will hold its dramatic Civil War Immersion weekend in Coon Valley

And 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.

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.

Last updated on October 10, 2018