MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Fall festivals 2019


  • (Sep. 7)Flugtag

    St. Paul, MN

    Red Bull comes to Harriet Island Park with its goofy flying-machine competition, in which showmanship and craft creativity are at least as important as flight distance (usually the homemade craft plunge straight into the water).

  • (Sep. 13 – 14)Oktoberfest

    St. Paul, MN

    The Germanic American Institute is producing this version of St. Paul's Oktoberfest at Schmidt Brewery in the West End. There will be a beer-wagon parade, a human glockenspiel, bed racing, dachshund racing, a stein-hoisting contest and a real German wedding in addition to music and dancing.

  • (Sep. 14)International Fall Festival

    Eau Claire, WI

    See the Parade of Nations, visit an international bazaar and listen to music on the World Stage.

  • (Sep. 14)Scarecrow Fest

    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.

  • (Sep. 20 – 21)Oaktoberfest

    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.

  • (Sep. 20 – 22)Hot Air Balloon Days

    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.

  • (Sep. 21 – 22)Festival of the Voyageur

    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.

  • (Sep. 21)Party on the Pavement

    Racine, WI

    Racine's biggest street festival features five stages of entertainment and a car show, art walk, carnival rides and zones for kids and sports.

  • (Sep. 25 – 29)Grundy County Corn Festival

    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.

  • (Sep. 27 – 29)Chainsaw Festival

    Hackensack, MN

    In this Brainerd-area lake town, watch 12 professional carvers turn logs into art. There will also be lumberjack/jill shows, horse racing, artisan booths and children's games.

  • (Sep. 28 – 29)All-State Barn Tour in Iowa

    Across the state, IA

    It's the Iowa Barn Foundation's annual free, self-guided tour of restored historic barns.

  • (Sep. 28)Fall Festival

    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.

  • (Sep. 28 – 29)Arts and Artists Celebration

    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.

  • (Sep. 28 – 29)Latino Heritage Festival

    Des Moines, IA

    This festival at Western Gateway Park features Latino music, dancing, arts, cultural booths, children's activities and a corn-eating contest.


  • (Oct. 4 – 6)Milwaukee Oktoberfest

    Milwaukee, WI

    There will be dachshund racing, stein-hoisting and brat-eating competitions as well as music and dancing in the plaza outside the Fiserv Forum arena.

  • (Oct. 5 – 6)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.

  • (Oct. 5 – 6)Olde English Faire/Autumn on Parade

    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. 5)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 a SodaFest with pop and stage entertainment for kids.

  • (Oct. 5 – 6)Fall Heritage Festival

    Mount Horeb, WI

    This town west of Madison offers fjord horses, buggy rides, a Norwegian breakfast, a mini tractor pull, rosemaling and lefse-making demonstrations and photo opps with Jorgen the Troll.

  • (Oct. 5 – 6)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.

  • (Oct. 11 – 12)Audubon Days

    Mayville, WI

    The festival in this town next to big Horicon Marsh features bed races, a car show, craft fair, bag tournament and music.

  • (Oct. 11 – 13)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.

  • (Oct. 11 – 12)Mystery at the Fur Post

    Pine City, MN

    Solve the mystery of "The Snake River Soap Opera'' at the re-created Snake River (formerly North West Company) Fur Post, an hour north of the Twin Cities. The program is family-friendly, and reservations are recommended.

  • (Oct. 11 – 13)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.

  • (Oct. 11 – 12)Pipestone Paranormal Weekend

    Pipestone, MN

    This town in the southwest corner of Minnesota concentrates on the supernatural, with a ghost walk, ghost hunt, cemetery tour, psychic gallery readings and tales from the grave.

  • (Oct. 11 – 13)St. Paul Art Crawl

    St. Paul, MN

    Stop by the studios of more than 400 artists in Lowertown and the Raymond-University area. 

  • (Oct. 12 – 13)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.

  • (Oct. 12 – 13)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.

  • (Oct. 17 – 20)Wisconsin Book Festival

    Madison, WI

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

  • (Oct. 18 – 19)Haven Harvest Festival

    South Haven, MI

    This downtown festival includes hayrides, a scarecrow contest, pumpkin-chucking, zombie runs, a pet-costume parade and a haunted asylum at the Maritime Museum.

  • (Oct. 19)Arts in the Dark Halloween parade

    Chicago, IL

    A parade with music, floats and puppets begins at 6 p.m. on State Street at Lake. There's a party afterward in Millennium Park, with stilt walkers and performance artists.


  • (Oct. 19)Oktoberfest

    Alexandria, MN

    Carlos Creek Winery's former Applefest will include nail-driving and stein-holding contests, craft beer, pumpkin tic-tac-toe, horse-drawn wagon rides and live bands.



  • (Oct. 25 – 26)Halloween Outdoor Puppet Extravaganza

    St. Paul, MN

    This all-ages evening spectacle in Hidden Falls Regional Park features larger-than-life puppetry, fire, song, stilting and, after the performance, food and dancing to the jazz brass bands.

    Suggested donation is $10-$20.

  • (Oct. 25 – 26)Zombie Days

    Washburn, WI

    Zombies will take over this town on Chequamegon Bay, and there's also a haunted hallway, carved-pumpkin contest and 2 p.m. Saturday parade.

  • (Oct. 26)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.

  • (Oct. 26)Freakfest

    Madison, WI

    This fest along State Street features music on three stages, outdoor horror movies, a costume contest with prizes and much sampling at bars. Headliners include the Gin Blossoms and Lil Yachty. 

  • (Oct. 26)Brothers Grimm Fairytale Halloween

    Green Bay, WI

    At Heritage Hill Historical Park, meet Snow White, Rapunzel and Rumpelstiltskin, hear stories, make crafts and play games.

  • (Oct. 26)BatFest

    Batavia, IL

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

  • (Oct. 31 – Nov 3)Driftless Film Festival

    Mineral Point

    See independent films and meet filmmakers in the 1916 opera house of this artistic town west of Madison.


  • (Nov. 1 – 2)Witching Hour Festival

    Iowa City, IA

    This festival focuses on the creative processes of musicians, artists, comedians, writers, thinkers, scientists and magicians. 

  • (Nov. 16)Veterans Day Parade

    Milwaukee, WI

    It's at 11 a.m., starting in Pere Marquette Park and following Kilbourn Avenue toward the lakefront. This year, it marks the 75th anniversary of D-Day.