MidwestWeekends.com — Your Travel Guide to the Upper Midwest
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September 2021  October 2021 November 2021
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Oktoberfest

La Crosse, WI

At this big riverfront festival, there's food, music and carnival rides, plus the opening Torchlight Parade and the Maple Leaf Parade on Saturday morning.

Sat
2
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Fri
1

Chain O' Lakes Blues Festival

Waupaca, WI

Listen to the blues at the historic Indian Crossing Casino.

CelebrAsian Asian Heritage Festival

Des Moines, IA

This festival at Western Gateway Park features such activities as martial arts, lion dancers, chopstick races, a fashion show and, of course, food.

Sun
3
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Fri
1

Apple Festival

Bayfield, WI

It's the 60th year of this big festival on Lake Superior, which features  orchard tours, history walks, an apple-peeling contest, live music and a big parade at 2 p.m. Sunday.

Oktoberfest

Amana, IA

There's German music and food at this Amana Colonies village, plus contests that include the Eisenmann, or Iron Man, competition: Teams roll kegs, walk a balance beam with full steins of beer and saw logs. The parade is at 10 a.m. Saturday.

Door County Lighthouse Festival

Sturgeon Bay, WI

The Door County Maritime Museum sponsors tours by air, land and water to lighthouses on the peninsula, some of which can be visited only during festival weekends. Reserve as early as possible.

Sat
2

Apple Affair

Galesville, WI

In the bluffs above Trempealeau, this festival features a 10-foot apple pie, a hunt for a Silver Apple, a race of floating wooden apples and a bicycle tour with a 20-mile route through apple orchards and hillier 35- and 60-mile routes.

Oktoberfest

Galena, IL

The Lions Club puts on this riverfront festival, which includes wiener-dog races, polka lessons, nail-driving, pumpkin-decorating and a beanbag tournament.

Northside Oktoberfest

Iowa City, IA

The Iowa City Brewfest is part of this festival, which includes keg bowling, beer sliding and nail-striking as well as traditional Oktoberfest music in an outdoor beer hall.

Sun
3
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Sat
2

Big Island Rendezvous and Festival

Albert Lea, MN

This southern Minnesota festival is great for families, with a voyageur encampment of more than 1,000 reenactors dancing, demonstrating, competing and pulling visitors back into the fur-trade era.

Oktoberfest

Cedarburg, WI

This festival just north of Milwaukee features music and food plus goofy contests: best lederhosen/dirndl, sauerkraut-eating, a German spelling bee and a live Glockenspiel show.

Giant Pumpkin Fest

Nekoosa, WI

This town near Wisconsin Rapids calls itself the Giant Pumpkin Capital of Wisconsin and features a pumpkin-pie eating contest, pumpkin rolling and carving, a carnival and craft show.

Autumn on Parade

Oregon, IL

Strolling performers appear at the Autumn on Parade Festival, and the Harvest Time Parade is on Sunday.

The Stronghold Conference Center outside town offers Olde English Faire on the same weekend, featuring swordfighters, minstrels, magicians and the Gremlin's Garden for children. However, it may not be held in 2021.

Fall Village Market

Mount Horeb, WI

This town west of Madison offers vintage and handmade goods, live music and food trucks.

 

Rivertown Fall Art Festival

Stillwater, MN

This juried arts festival along the banks of the St. Croix River includes music and food vendors.

Cranberry Fest

Eagle River, WI

In this northeast Wisconsin lakes town, there will be marsh tours, music, a cranberry beer and wine garden, an antiques market, fiber-art show and crafts fair.

Sun
10
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Fri
8

Scenic Drive Festival

Van Buren County, IA

In the southeast corner of Iowa, 11 villages feature quilt shows, scarecrow contests, bake sales, tours of historic sites, wine tasting and street fairs.

Northeast Iowa Artists' Studio Tour

Decorah area, IA

Drive through bluff country to see 56 artists at 43 sites around Decorah, Burr Oak, St. Lucas, Waukon, West Union, Cresco, New Albin, Lansing, Elgin and Clermont.

Scarecrow Festival

St. Charles, IL

There's a big scarecrow contest plus a carnival, music, dance and the Autumn on the Fox arts show in this town west of Chicago. New this year is the Family Zone.

Pumpkin Festival

Highwood, IL

Every year, this northern suburb of Chicago tries to break the record for most lighted jack-o-lanterns. In addition to all-you-can-carve stations, there will be costume, pie-eating and carving contests.

Apple Festival

Charlevoix, MI

In this Lake Michigan town, there's a pumpkin-carving contest, children's activities and an arts and crafts show.

Covered Bridge Studio Tour

Cedarburg, WI

This studio tour in eastern Wisconsin includes more than 60 artists in Cedarburg, Grafton, Port Washington, Mequon, Thiensville and Newburg.

 

Sat
9

Civil War Immersion Weekend at Norskedalen

Coon Valley, WI

This pioneer farmstead in the coulees southeast of La Crosse is wonderfully atmospheric, and the crackerjack re-enactors of the Second Wisconsin Volunteer Infantry's Company B give the region's most affecting portrayal of war.

Sun
10
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Sat
9

Madison County Covered Bridge Festival

Winterset, IA

John Wayne was born there, George Washington Carver lived there and the famous covered bridges still are there. The festival in this town southwest of Des Moines features guided bus tours to the bridges, free horse-drawn wagon rides to Wayne's house, Old West shootouts, live music and a parade at 2 p.m. Sunday.

Galena Country Fair

Galena, IL

There's a juried fine arts/arts and crafts fair, farmers market, wine garden, bake shop, music and children's games in Grant Park.

Pumpkin Patch Festival

Egg Harbor, WI

There'll be music, children's games and arts and crafts in this Door County village.

Oktoberfest

Lake Geneva, WI

There will be music, food and free pumpkins on downtown streets.

Burgoo Festival

Utica, IL

The street party in this northern Illinois town, gateway to Starved Rock State Park, features vats of "pioneer'' stew, a crafts fair and music.

Harvest Fest

Stillwater, MN

In this river town, there will be a pumpkin pie-eating contest, a pumpkin regatta on the St. Croix, a microbrew tasting and a pedal tractor pull.

Shadows of the Blue and Gray

Princeton, IL

This Civil War festival off I-80, half an hour west of Starved Rock State Park, includes battle re-enactments both days.

There will also be a Grand Entrance parade with the Lincolns, a Lincoln look-alike contest, medical scenarios and period music and dance.

Sun
10

Harvest Fest

New Glarus, WI

See old-time artisanry at the Swiss Historical Village, including sausage-stuffing and cheese-making in the 1890s cheese factory.

Sun
24
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Wed
13

Chicago International Film Festival

Chicago, IL

This year's program includes 65 films and nine programs of shorts that are screening at the ChiTown Movies Drive-In in Pilsen.

Sun
17
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Fri
15

Fall Festival

Sister Bay, WI

This Door County festival features pumpkin bowling, a derby race, chainsaw carving, a pingpong-ball drop and a parade at 11 a.m. Saturday.

Southwest Wisconsin Fall Art Tour

Southwest, WI

This popular studio tour includes artists at studios between Mineral Point, Spring Green, Dodgeville and Baraboo.

Sat
16

Oktoberfest

Elkhorn, WI

This downtown festival near Lake Geneva features wine and beer tasting, music, a car show, arts and crafts and a chili cookoff.

Jack O' Lantern Festival

Spooner, WI

There's a pumpkin-carving and scarecrow-making contests, kids' inflatables, pumpkin roll and, in the evening, a zombie run in the forest, bonfires and live music.

Family Fall Fest

Madeline Island, WI

On the largest of the Apostle Islands, there will be a vintage-car show, cider- and soap-making, pumpkin decorating, a pie-eating contest, street vendors and a kids' costume parade.

Sun
17
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Sat
16

Open House Chicago

Chicago, IL

The Chicago Architecture Foundation sponsors this free, behind-the-scenes peek at more than 200 mansions, clubs, churches, hotels and theaters.

Sun
24
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Mon
18

Iowa City Book Festival

Iowa City, IA

The first North American town to be named a UNESCO City of Literature offers talks, readings, panels, exhibits and a walking tour of literary Iowa City.

Sun
24
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Thu
21

Wisconsin Book Festival

Madison, WI

This big fest features readings, lectures, book discussions, writing workshops, live interviews and children's events.

Sat
23
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Fri
22

Moose Madness Festival

Grand Marais, MN

This Lake Superior town offers  a medallion hunt, family geocaching contest, fun run, appearances by Murray the Moose and family courses at the North House Folk School.

Sun
24
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Fri
22

Autumnfest

St. Croix Falls, WI

This town on the St. Croix River offers live music, a car show, food trucks and an arts and crafts fair in Overlook Park.

Sat
23

Oktoberfest

Alexandria, MN

Carlos Creek Winery's brewing partner, 22 Northmen, hosts this festival, which includes a stein-holding contest, pumpkin throwing, horse-drawn wagon rides and live bands.

 

 

Pumpkin Chuckin Fest

Union Grove, WI

The festival in this town, just west of Racine, features a pumpkin catapult contest, barbecue cook-off, pie auction, pumpkin-baking contest, children's games and music.

Sun
24
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Sat
23

Earth Wood & Fire Artist Tour

Lake Mills, WI

Visit artists in their studios in and around Lake Mills, Cambridge and Fort Atkinson, between Madison and Milwaukee.

Sat
30
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Sat
23

Halloween

Anoka, MN

This town, just north of Minneapolis, calls itself the Halloween Capital of the World. Festivities include a house-decorating contest and a Grande Day Parade.

Sun
24

Witches & Wizards of Woodstock

Woodstock, IL

This all-ages fantasy festival in Woodstock Square features a magical talking hat, Quidditch training, an owlery, a wandering magician, a cosplay scavenger hunt and a costume parade and contest.

Sun
31
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Wed
27

Pumpkin Festival

Sycamore, IL

In this town between Rockford and DeKalb, there will be a pie-eating contest, carnival, craft shows, decorated pumpkins and a parade Sunday.

Sun
31
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Fri
29

Jack O'Lantern Days

Fish Creek, WI

There will be mask making, pumpkin carving, trick or treating and haunted trolley tours.

Zombie Days

Washburn, WI

Zombies will take over this town on Chequamegon Bay, and there are also carved-pumpkin, costume and house-decorating contests, a ghost hunt and a drive-in movie.

Sat
30

UFO Day

Belleville, WI

There's a craft fair, kids' games and a Forbidden Forest, but the 1 p.m. parade is the main event in this riverside village just south of Madison, where residents reported more than a dozen UFO sightings in the winter of 1987.

Arts in the Dark Halloween parade

Chicago, IL

Floats, giant puppets and performances are part of the 6-8 p.m. parade along State Street.

 

Halloween Parade & Festival

Galena, IL

There will be hot-air balloons in the morning, kids' activities and a food festival in the afternoon, and the town's annual parade along Main Street at 6:30 p.m.

BatFest

Batavia, IL

This Fox River town hosts a pumpkin roll, pumpkin-carving battles, "Thriller'' dances, marshmallow shooting and a parade.

Mount Carroll Pumpkin Fest

Mount Carroll, IL

In this northwest Illinois town, there will be a costume parade, pumpkin bowling, pumpkin slingshot and pumpkin street drag races.

Day of the Dead Xicago

Chicago, IL

In the National Museum of Mexican Art and Harrison Park, families can create ofrendas (altars), eat pan de muerto, listen to musical performances and get faces painted. Admission is free.

Sun
31

Halloween Outdoor Puppet Extravaganza

Minneapolis, MN

This year, the larger-than-life puppetry troupe will collaborate on The Cry of the Ancestors, a community pageant procession from Powderhorn Park, with the theme being grief, loss and death.