MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Great fall festivals

Here are the best of the autumn fests in 2021.

A carriage race at Villa Louis.

© Wisconsin Historical Soci

Drivers in vintage clothes race carriages during the Carriage Classic at Villa Louis.

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.

Before you go, check 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.

Dachshund races at a festival.

© Beth Gauper

Dachshund races are held at many fall festivals.

Second weekend in September

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. 8–12.

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. 8–12.

Summerfest in Milwaukee, WI They call this the world's largest music festival. More than 1,000 acts perform on 12 stages along Lake Michigan.  Sept. 9–11.

James J. Hill Days in Wayzata, MN This Minneapolis suburb features a street market and carnival; dachshund races, a craft-beer fest, logrolling and fireworks on Saturday; and a parade on Sunday. Sept. 10–12.

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. 10–12.

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. 10–12.

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. 10–12.

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. 10–12.

Classic Boat & Schooner Rendezvous in Bayfield, WI Schooners and sloops will gather in this Lake Superior town. There will be activities for children, an open house at the Coast Guard station and a Saturday boat parade. Sept. 10–12.

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. Sept. 11.

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 $7 vehicle permit. There also will be camping and food vendors. Sept. 11.

Taste of the Trail in Lanesboro, MN In Lanesboro, Whalan and Peterson on the Root River State Trail, enjoy music, wagon rides and free samples from local restaurants and growers.  Events are from 10 a.m. to 2 p.m. Sept. 11.

Driftless Music Festival in Viroqua, WI This free folk and roots festival is in Viroqua's Eckhart Park. Sept. 11.

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. 11.

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. 11.

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. 11.

Radio Waves Music Festival in Grand Marais, MN WTIP, North Shore Community Radio, hosts this outdoor fest of more than 25 local and regional music acts next to the municipal campground. Sept. 11.

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. 11–12.

Rock Bend Folk Festival in St. Peter, MN This free, easygoing festival is in this Minnesota River town's Minnesota Square Park. Sept. 11–12.

Little Falls Arts & Crafts Fair in Little Falls, MN This large fair, with nearly 600 artists, includes a car show and an antiques and collectibles section as well as a Man Cave. Sept. 11–12.

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. 12.

Scandinavian Day in South Elgin, IL This festival in Vasa Park, along the Fox River, features music, dancing, food and crafts from the Nordic countries. Sept. 12.

Cheese Days parade in Monroe.

©

Bernese mountain dogs pull a flower cart during the Cheese Days parade in Monroe.

Third weekend in September

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. The festival features pumpkin-boat races, pumpkin decorating, pie-eating contests, a craft fair, a pumpkin-pancake breakfast and a 10:30 a.m. Saturday parade. Sept. 15–18.

Summerfest in Milwaukee, WI They call this the world's largest music festival. More than 1,000 acts perform on 12 stages along Lake Michigan.  Sept. 16–18.

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. 16–19.

Oktoberfest in Chippewa Falls, WI Meet the Narren, enter a sauerkraut-eating contest, listen to polka and zydeco and watch the daily parade. Sept. 17–18.

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. 17–19.

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. This year, the festival has been altered; check for events. Sept. 17–19.

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. 17–19.

Grape Stomp in Alexandria, MN Carlos Creek Winery hosts this festival, which features music on two stages, an art fair, grape stomps and "I Love Lucy'' look-alike contests.   Sept. 17–19.

Riot Fest in Chicago, IL This Douglas Park music festival also features a circus sideshow revue and carnival. Sept. 17–19.

Wauktoberfest in Waunakee, WI This town just north of Madison celebrates with a craft-beer tasting, bike tour, music and lots of contests: frau carrying, yodeling, beer keg race, dachshund dash and Limburger cheese and sauerkraut eating. Sept. 17–19.

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. 17–19.

Hot Air Balloon Days in Creston, IA In this town southwest of Des Moines, there are balloon races and night glows, a parade with marching-band contest, an arts and crafts fair and a flea market. Sept. 17–19.

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. 18.

Taste of the Trail in Fountain/Preston/Harmony, MN On the Harmony-Preston Valley State Trail, sample local treats, listen to music, visit the National Trout Center, take wagon rides and play games.   Sept. 18.

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. 18.

Harvest Fest & Street Art Auction in Sturgeon Bay, WI This street party includes a car show, cornhole and chalk-art contests, music and artisans and winds up with the auction of 25 artist-created cherries. Sept. 18.

Museum Day in Every state, Smithsonian magazine and participating museums in every state offer free admission for two people. Tickets are available for download on the website. Sept. 18.

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. 18–19.

Vintage Illinois Wine Festival in Utica, IL This festival in northwest Illinois features live music and wine-tasting from 25 Illinois vineyards.   Sept. 18–19.

Art and Apples on the Lake in Excelsior, MN On the shore of Lake Minnetonka, Art on the Lake combines with Apple Day, with an art fair, apple pie-eating contest, music and a street dance. Sept. 18–19.

Fourth weekend of September

Boats and Bluegrass in Winona, MN This family-oriented festival in Prairie Island Park, on the Mississippi River, features disc golf and paddling as well as music. A weekend pass includes camping and canoeing, and kids under 16 are free with an adult ticket. Buy tickets early to save money. Sept. 23–25.

Oktoberfest in New Glarus, WI There will be music, wagon rides, chainsaw carving, children's activities and, of course, beer from New Glarus Brewing. Sept. 23–26.

German Fest in Guttenberg, IA There will be music, dancing, children's games and lock and dam tours in this antebellum town on the Mississippi River. Sept. 24–25.

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. 24–25.

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. 24–25.

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. 24–25.

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. 24–26.

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. 24–26.

Cranberry Festival in Warrens, WI At this huge festival in west-central Wisconsin, there'll be marsh tours, pie-eating contests and more than 1,000 booths selling antiques, produce and arts and crafts. The big parade is at 1 p.m. Sunday. Sept. 24–26.

Fall Festival in Hayward, WI There's an arts and crafts fair, children's games, contests and live music downtown. Sept. 25.

Taste of the Trail in Rushford/Houston, MN On the Root River State Trail, sample local food, listen to music, tour a museum and visit the International Owl Center. Sept. 25.

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. 25.

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. 25.

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. 25–26.

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. 25–26.

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. This year, the festival is virtual on Saturday, but on Sunday there will be live music on mobile stages in Hyde Park. Sept. 25–26.

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.   Sept. 25–26.

Civil War re-enactors march at Norskedalen.

© Beth Gauper

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

First weekend in October

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. 30–Oct. 3.

Chain O' Lakes Blues Festival in Waupaca, WI Listen to the blues at the historic Indian Crossing Casino. Oct. 1–2.

CelebrAsian Asian Heritage Festival in 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. Oct. 1–2.

Apple Festival in 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. Oct. 1–3.

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. 1–3.

Apple Affair in 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. Oct. 2.

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. Oct. 2.

Big Island Rendezvous and Festival in 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. Oct. 2–3.

Oktoberfest in 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. Oct. 2–3.

Giant Pumpkin Fest in 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. Oct. 2–3.

Olde English Faire/Autumn on Parade in Oregon, IL This festival at Stronghold Conference Center features swordfighters, minstrels, magicians and the Gremlin's Garden for children. In town, more strolling performers appear at the Autumn on Parade Festival, and the Harvest Time Parade is on Sunday. Oct. 2–3.

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. 2–3.

Cranberry Fest in 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. Oct. 2–3.

Second weekend of October

Scenic Drive Festival in 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. Oct. 8–10.

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. 8–10.

Pumpkin Festival in 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. Oct. 8–10.

Apple Festival in Charlevoix, MI In this Lake Michigan town, there's a pumpkin-carving contest, children's activities and an arts and crafts show. Oct. 8–10.

Covered Bridge Studio Tour in Cedarburg, WI This studio tour in eastern Wisconsin includes more than 60 artists in Cedarburg, Grafton, Port Washington, Mequon, Thiensville and Newburg.   Oct. 8–10.

Madison County Covered Bridge Festival in 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. Oct. 9–10.

Galena Country Fair in 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. Oct. 9–10.

Pumpkin Patch Festival in Egg Harbor, WI There'll be music, children's games and arts and crafts in this Door County village. Oct. 9–10.

Burgoo Festival in 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. Oct. 9–10.

Shadows of the Blue and Gray in 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. Oct. 9–10.

Laura look-alikes compete in Pepin.

© Beth Gauper

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

Third weekend of October

Chicago International Film Festival in 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. Oct. 13–24.

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. 15–17.

Oktoberfest in Elkhorn, WI This downtown festival near Lake Geneva features wine and beer tasting, music, a car show, arts and crafts and a chili cookoff. Oct. 16.

Pumpkin Chuckin Fest in 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. Oct. 16.

Family Fall Fest in 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. Oct. 16.

A float from the La Crosse Oktoberfest parade.

© Beth Gauper

In La Crosse, Oktoberfest stretches across nine days.

Fourth weekend of October

Chicago International Film Festival in 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. Oct. 13–24.

Moose Madness Festival in 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. Oct. 22–23.

Autumnfest in 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. Oct. 22–24.

Oktoberfest in 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.     Oct. 23.

Earth Wood & Fire Artist Tour in Lake Mills, WI Visit artists in their studios in and around Lake Mills, Cambridge and Fort Atkinson, between Madison and Milwaukee. Oct. 23–24.

Halloween in 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. Oct. 23–30.

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.

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.

Halloween in 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. Oct. 23–30.

Pumpkin Festival in 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. Oct. 27–31.

Jack O'Lantern Days in Fish Creek, WI There will be mask making, pumpkin carving, trick or treating and haunted trolley tours. Oct. 29–31.

Halloween Parade & Festival in 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. Oct. 30.

First weekend in November

Big Water Film Festival in Ashland, WI See a variety of shorts, full-length films and documentaries at the Bay Theater downtown. Nov. 3–6.

Art Attack in Minneapolis, MN In the northeast arts district, 350 artists open their studios and offer demonstrations and workshops.  Nov. 5–7.

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.

Second weekend in November

Gales of November in Duluth, MN Listen to experts discuss Lake Superior shipwrecks and maritime history and join tours of the aquarium and Coast Guard Center. Nov. 12–13.

Winter Art Fair Off the Square in Madison, WI Art Fair Off the Square presents its winter edition in Monona Terrace, with 140 fine artists from around Wisconsin. Nov. 13–14.

Holiday Fantasy in Lights in Madison, WI The free display in Olin Park is open from dusk to dawn. Nov. 13–Jan. 2.

For more, see Great holiday festivals.


Last updated on May 14, 2021