MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Great fall festivals

Here are the best of the autumn fests in 2018.

A wall of jack-o-lanterns in Highwood.

© Highwood Chamber

Every October, the town of Highwood, Ill., tries to best its own world record for the most carved and lighted pumpkins.

Fall is made for festivals. It's harvest time, and the fields and orchards are overflowing. Trees turn red and gold. And it's the last time we'll enjoy warm weather until spring.

The many people who heed the urge to get out and about on crisp autumn weekends make it the busiest tourist season of the year.

Any town that can hold a fall festival does, and well-established ones, such as Bayfield's Apple Festival (see Big apples), become almost too popular.

Other festivals also attract big crowds Cranberry Fest in west-central Wisconsin, the Fall Art Tour in southwest Wisconsin and people who haven't reserved lodgings may not be able to get them.

All Oktoberfest celebrations are popular; for a list, see Toasting Oktoberfest.

But small festivals also attract a lot of people, and leaf-peepers will be out en masse in the north woods and along the St. Croix and Mississippi rivers (see Great fall drives). Many people combine scenic drives with artist tours (see Autumn in the studios). 

So if you want to travel in fall, plan ahead.

Here are some of the best festivals in 2018. Always check before you go to verify dates and to make sure you catch the best parts of a festival, especially the parades.

For small-town festivals, see Bash on a bike trail.

For art tours, see Autumn in the studios.

For events year-round, see the Events Calendar.

Second weekend in September

Sandwich Fair in Sandwich, IL This northeast Illinois fair, held since 1888, features exhibits, entertainment and music plus harness racing, tractor pulls and demolition derbies. Sept. 5–9.

Defeat of Jesse James Days in Northfield, MN In this college town south of the Twin Cities, there's a fine-arts festival, tractor pulls, a bike tour, reenactments of the famous bank raid and a Sunday parade. Sept. 6–9.

Pufferbilly Days in Boone, IA This festival in central Iowa, just west of Ames is named for a steam engine and features Civil War battle reenactments, mud volleyball and rides on the Boone and Scenic Valley Railroad. A parade is Saturday. Sept. 6–9.

La Crosse Storytelling Festival in La Crosse, WI Listen to local, regional and national storytellers spin tales in Myrick Park. Sept. 7–8.

Sputnikfest in Manitowoc, WI Help celebrate the 1962 crash landing of a 20-pound piece of Russia's Sputnik on a street in Manitowoc. There's a wacky costume contest, a Miss Space Debris pageant, a pet costume contest, a space-themed movie and music. Sept. 7–8.

James J. Hill Days in Wayzata, MN This Minneapolis suburb features a street market and carnival; dachshund races, a craft-beer fest, water-ski show and fireworks on Saturday; and a parade on Sunday. Sept. 7–9.

Indian Summer Festival in Milwaukee, WI This lakefront festival features a powwow, canoe rides, cooking demonstrataions, Aztec dancers and lacrosse lessons. Sept. 7–9.

Villa Louis Carriage Classic in Prairie du Chien, WI The Victorian estate on the Mississippi River hosts horses, restored carriages and drivers in period dress for competitive arena and cross-country sport driving, a passion of the frontier aristocrats who built it. Sept. 7–9.

Festival of the Vine in Geneva, IL There's an arts and crafts show, flower market, music, wine tasting and sampling of food from local restaurants. Sept. 7–9.

Paw Paw Wine & Harvest Festival in Paw Paw, MI This big festival in southwest Michigan wine country features music on three stages, Friday fireworks, an art fair, motorcycle and bicycle tours, grape stomps and a Sunday parade. Sept. 7–9.

Harvest Moon Festival in Ely, MN In Whiteside Park, there's an arts fair plus music, an old-time medicine show and pony rides and a petting zoo for kids. Sept. 7–9.

World Music Festival in Chicago, IL There will be more than 80 artists performing at more than 30 venues across the city, including the Chicago Cultural Center. Admission is free. Sept. 7–23.

Ethnic Fest in Walker, MN Alphornists, Scandinavian dancers and Anishinaabe drum and dance corps perform in this town on the shores of Leech Lake. There's also a parade at 11 a.m. Sept. 8.

Washington County Bluegrass Festival in Lake Elmo, MN Bluegrass bands will play at this family festival at Lake Elmo Park Reserve at the eastern edge of the Twin Cities, free with $5 vehicle permit. There also will be camping and food vendors. Sept. 8.

Mural Fest in Ashland, WI Go on guided tours of Ashland's famous murals, meet the artists and go on a mural scavenger hunt. There's also food, music, crafts and a car show. Sept. 8.

Whooping Crane Festival in Princeton, WI Celebrate the whooping-crane migration with voyageur canoe trips, a marketplace, crane trivia, children's activities and bird walks. Sept. 8.

Laura Ingalls Wilder Days in Pepin, WI The famous author's birthplace  celebrates with kids' pioneer games, a spelling bee and traditional music and crafts; pie-eating, fiddle and Laura contests; and a Sunday parade. Sept. 8–9.

St. Paul Classic Bike Tour in St. Paul, MN Ride a 15-, 30- or 45-mile route along the Mississippi, lakes Como and Phalen and St. Paul parkways, starting and ending at the University of St. Thomas and punctuated by food and live music. Sept. 9.

Bayfield Apple Fest royalty wave from a giant float.

© Beth Gauper

The local homecoming king and queen ride a giant apple in Bayfield's big Apple Fest parade.

Third weekend in September

World Music Festival in Chicago, IL There will be more than 80 artists performing at more than 30 venues across the city, including the Chicago Cultural Center. Admission is free. Sept. 7–23.

Pumpkin Festival in Morton, IL This town near Peoria, home of the Libby's pumpkin-packing plant, calls itself the Pumpkin Capital of the World and serves pumpkin ice cream, pancakes and fudge at its festival, which features a 10:30 a.m. Saturday parade. Sept. 12–15.

Michigan Irish Music Festival in Muskegon, MI There's music on three stages, plus dance and session tents, a cultural village, Celtic Kitchen and limerick contest. Sept. 13–16.

Oaktoberfest in Oak Park, IL In this western suburb of Chicago, famous for its Frank Lloyd Wright district, there's music, craft beer, food from local restaurants and, for kids, a root-beer garden, games and zucchini-car races. Sept. 14–15.

Wo-Zha-Wa Days in Wisconsin Dells, WI There's a juried arts and crafts show,a flea maraket, a street carnival and a parade Sunday. Sept. 14–16.

Oktoberfest in Chippewa Falls, WI Meet the Narren, enter a sauerkraut-eating contest, listen to polka and zydeco and watch the daily parade. Sept. 14–16.

Unplugged: The Northern Harvest in Grand Marais, MN The harbor-side North House Folk School celebrates with storytelling, traditional workshops, a fish boil and concerts by songwriter/musicians. Sept. 14–16.

World Food & Music Festival in Des Moines, IA In downtown's East Village, eat at more than 50 cultural cafes for $5 or less (or taste for $1), shop at the world marketplace or listen to musicians strolling the streets or on stage. Sept. 14–16.

Cheese Days in Monroe, WI This festival is held every other year in the capital of cheese country, the home of Swiss Colony and the last Limburger factory. There's a cow-milking contest, yodeling, dancing, tours and a big parade Sunday. Sept. 14–16.

Grape Stomp in Alexandria, MN Carlos Creek Winery hosts this festival, which features music on three stages, crafts, a logging show, Friday fire dancing and fireworks, grape stomps, "I Love Lucy'' look-alike contests and a reenactment of the Lucy "Grapes of Laugh'' episode. Sept. 14–16.

Riot Fest in Chicago, IL This Douglas Park music festival also features a circus sideshow revue and carnival. Sept. 14–16.

Gemuetlichkeit Days in Jefferson, WI This festival between Madison and Milwaukee is named for the German word for a cozy and congenial atmosphere. It includes sauerkraut-eating, nail-driving, facial hair and costume contests, a vintage car show, music and a parade at noon Sunday. Sept. 14–16.

Parade of Nations and Multicultural Festival in Hancock/Houghton, MI The parade begins in Hancock and ends in Houghton at Dee Stadium, where there's a festival with music, dancing and food from around the world. Sept. 15.

Scarecrow Fest in Phelps, WI See early fall color around this town in Nicolet National Forest. There's pumpkin-chucking, pumpkin and scarecrow contests, a craft fair, car show, hay rides and free chili and deep-fried pickles. Sept. 15.

Bay View Bash in Milwaukee, WI This street festival in the Bay View neighborhood includes music on four stages, a children's area, cooking demonstrations and a strong man competition. Sept. 15.

Wine & Harvest Festival in Cedarburg, WI There's a pumpkin regatta — yes, people paddling hollowed-out pumpkins across Cedar Creek — at the fest in this historic mill town just north of Milwaukee. There's also a scarecrow contest, grape stomp, hay rides, juried arts fair and lots of food. Sept. 15–16.

Festival of the Voyageur in Pine City, MN No one's more fun than a voyageur, and they'll be dancing, boasting and trying to best one another at this family-friendly event at the Snake River (formerly North West Company) Fur Post, an hour north of the Twin Cities. For the kids, there's a bead scramble, candle-dipping and a scavenger hunt. Sept. 15–16.

Vintage Illinois Wine Festival in Matthiessen State Park, IL This festival in northwest Illinois features live music and wine-tasting from 25 Illinois vineyards. Sept. 15–16.

Bacon Bash in River Falls, WI There will be pig races, a pig-calling contest, pig crafts, an amateur bacon cook-off and many bacon dishes, including ice cream. Sept. 15–16.

Minneapolis Bike Tour in Minneapolis, MN Ride 16, 25 or 32 miles on parkways along the Mississippi and the Chain of Lakes. Start and finish is Boom Island, along the river in northeast Minneapolis; there's a party afterward with food, music and beer. Sept. 16.

Fourth weekend of September

World Music Festival in Chicago, IL There will be more than 80 artists performing at more than 30 venues across the city, including the Chicago Cultural Center. Admission is free. Sept. 7–23.

Oktoberfest in 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. Sept. 22.

Arts and Artists Celebration in Taylors Falls, WI See the new art installations at Franconia Sculpture Park, just west of town, and watch art in progress. There will also be music, food and art-making for the whole family, such as spin art and face-painting. Sept. 22.

Apple Day in Excelsior, MN On the shore of Lake Minnetonka, there's an artisan fair, apple pie-eating contest, music and a street dance. Sept. 22.

All-State Barn Tour in Iowa in Across the state, IA It's the Iowa Barn Foundation's annual free, self-guided tour of restored historic barns. Sept. 22–23.

Spirit of the St. Croix Art Festival in Hudson, WI Music, food and a juried art show along the St. Croix River, in Lakefront Park. Sept. 22–23.

Doors Open Milwaukee in Milwaukee, WI More than 150 historic buildings — theaters, breweries, mansions, cathedrals, hotels, museums — are open to the public, and many offer free guided tours. More than three dozen in-depth walking tours also are offered but sell out quickly. Check in July for the program. Sept. 22–23.

Latino Heritage Festival in Des Moines, IA This festival at Western Gateway Park features Latino music, dancing, arts, cultural booths, children's activities and a corn-eating contest. Sept. 22–23.

Children's Halloween parade.

© Beth Gauper

Children march in a Halloween parade.

Fifth weekend of September

Grundy County Corn Festival in Morris, IL The festival in this town on the Illinois River between Ottawa and Joliet offers stagecoach and train rides, a crackerbox derby, a pie-eating contest, music, a carnival, Saturday fireworks and a parade at 2 p.m. Sunday. Sept. 26–30.

Oktoberfest in 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. Sept. 27–30.

Boats and Bluegrass in Winona, MN This family-oriented festival in Prairie Island Park, on the Mississippi River, features disc golf, paddling and airplane rides as well as music. A weekend pass includes camping and canoeing, and kids under 16 are free with an adult ticket. Sept. 27–30.

Milwaukee Oktoberfest in Milwaukee, WI There will be dachshund racing, stein-hoisting and brat-eating competitions as well as music and dancing in MacArthur Square, a new location. Sept. 27–Oct. 7.

Fall Fest in Cable, WI In the colorful northwest Wisconsin woods, there'll be hay rides, corn maze, a chili cook-off, fish boil, arts and crafts and fireworks. Sept. 28–29.

Kalona Fall Festival in Kalona, IA This Mennonite community just southwest of Iowa City, famous for its quilts, offers pony rides, a pumpkin-carving contest, demonstrations of Old World artisanry, music and homemade potato chips, apple fritters, ice cream and chicken, biscuits and gravy. Sept. 28–29.

Oktoberfest in Des Moines, IA Take polka-dancing lessons, enter the Bier Maiden or stein-holding contests and win costume prizes at this outdoor fest under tents downtown. Sept. 28–29.

Octoberfest in Appleton, WI This large downtown festival is more general civic celebration than German festival, with an arts and crafts show, car show and music on five stages. Sept. 28–29.

Cornish Festival in Mineral Point, WI In the old lead-mining district in southwest Wisconsin, play shove ha'penny in the Kiddleywink Pub, eat figgyhobbin and pasties, listen to tommyknocker tales and tour Cornish miners' cottages. Sept. 28–30.

Apple Festival in Gays Mills, WI There'll be arts and crafts and music in this southwest Wisconsin village. The big parade is Sunday. Sept. 28–30.

Cranberry Festival in Warrens, WI At this huge festival in west-central Wisconsin, there'll be marsh tours, pie-eating contests and more than 1,300 booths selling antiques, produce and arts and crafts. The big parade is at 2 p.m. Sunday. Sept. 28–30.

Beef-A-Rama in Minocqua, WI In this northern Wisconsin lake-resort town, there's a Rump Roast Run, beef-eating contest and Parade of Beef. Sept. 29.

International Fall Festival in Eau Claire, WI See the Parade of Nations, an international bazaar and music on the World Stage. Sept. 29.

Johnny Appleseed Festival in Crystal Lake, IL In this northwest suburb of Chicago, there's pumpkin bowling, a pumpkin train and petting zoo, apple contests, music and a craft fair. Sept. 29.

Oktoberfest in Sault Ste. Marie, MI Beer-barrel relay races, polka lessons, a farm  market and a tug of war are part of this downtown festival. The Sault International Marathon is held in the morning. Sept. 29.

Civil War Weekend in Greenbush, WI Battles are reenacted at this festival at the Wade House historic site near Sheboygan. There's also a traveling medicine show, court martials, a sutler's row, period concerts and appearances by Abraham Lincoln. Sept. 29–30.

Tour of Historic Galena Homes in Galena, IL Tour five private homes and the History Museum in this picturesque town in northwest Illinois. Sept. 29–30.

Hyde Park Jazz Festival in Chicago, IL Listen to non-stop music during this free festival at venues in and around Midway Plaisance, near the Museum of Science and Industry and Lake Michigan. Sept. 29–30.

Summit Hill House Tour in St. Paul, MN This self-guided tour of homes on one of the nation's best-preserved Victorian streets is held only once every two years.  Sept. 30.

Millstream Arts Festival in St. Joseph, MN In addition to a juried art show, the festival in this town at the start of the Lake Wobegon Trail also features music, street performances, history tours and a vintage car and tractor show. Sept. 30.

Apple Festival in Bayfield.

© Beth Gauper

In Bayfield, Apple Festival draws crowds.

First weekend in October

Milwaukee Oktoberfest in Milwaukee, WI There will be dachshund racing, stein-hoisting and brat-eating competitions as well as music and dancing in MacArthur Square, a new location. Sept. 27–Oct. 7.

Apple Festival in Bayfield, WI It's the 57th 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. Oct. 5–7.

Oktoberfest in 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. Oct. 5–7.

Rivertown Fall Art Festival in Stillwater, MN This juried arts festival along the banks of the St. Croix River includes music and food vendors. Oct. 6–7.

Second weekend of October

Northeast Iowa Artists' Studio Tour in 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. Oct. 12–14.

Fall Festival in Sister Bay, WI This Door County festival features pumpkin bowling, chainsaw carving, a pingpong-ball drop and a parade at 11 a.m. Saturday. Oct. 12–14.

Third weekend of October

Southwest Wisconsin Fall Art Tour in Southwest, WI This popular studio tour includes artists at studios between Mineral Point, Spring Green, Dodgeville and Baraboo. Oct. 19–21.

Applefest in Alexandria, MN Enter a pie-eating contest, listen to bands, go on a horse-drawn wagon ride and watch a pumpkin-catapult contest and quilt auction at Carlos Creek Winery. Oct. 20.

Laura look-alikes compete in Pepin.

© Beth Gauper

Laura look-alikes compete during Laura Ingalls Wilder Days in Pepin, Wis.

Halloween weekend

Over Halloween, anything that can be haunted zoos, airplane hangars, corn mazes, nature centers, historic houses, cemeteries, trolleys and trains will be haunted. For more, see Horror around the corner.

And tours make the rounds of ghost haunts in Chicago, Galena, St. Paul, Wausau and other towns. For more, see Ghosts on the prowl.

Jack O'Lantern Days in Fish Creek, WI There will be mask making, pumpkin carving, trick or treating and a Halloween parade at 1:30 p.m. Saturday. Oct. 26–28.

Halloween Parade in Galena, IL The town's annual parade is along Main Street at 6:30 p.m. Oct. 27.

First weekend in November

Civil War re-enactors march at Norskedalen.

© Beth Gauper

Re-enactors march through Norskedalen during Civil War Weekend in southwest Wisconsin.

Second weekend in November

For more, see Great holiday festivals.


Last updated on March 16, 2018