MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Fall festivals 2020


  • (Jul 24 – 25)La Crosse Storytelling Festival

    La Crosse, WI

    Listen to local, regional and national storytellers spin tales at the Pump House. There will also be music and arts and crafts.


  • (Aug. 21 – 23)Art & Big Fork Festival

    Evanston, IL

    This downtown festival features live music and local food, beer, wine and fine art.


  • (Sep. 5)Mural Fest

    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.

  • (Sep. 6)Virtual World Music Festival

    Chicago, IL

    The festival will be presented online 1-3 p.m. on Sundays in September.

    Normally, there will be more than 80 artists performing at more than 30 venues across the city, including the Chicago Cultural Center. 

  • (Sep. 12)Monarch Festival

    Minneapolis, MN

    This festival at Lake Nokomis celebrates the monarch migration from Minnesota to Mexico and includes a costume parade, music, dance, art activities and monarch games.

  • (Sep. 16 – 19)Pumpkin Festival

    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.

    This year, the parade is drive-through and some events are canceled.

  • (Sep. 18 – 19)Unplugged & Birch Bark Bash

    Grand Marais, MN

    The harbor-side North House Folk School celebrates with storytelling, traditional workshops, a fish boil and concerts by songwriter/musicians.

    It's online this year.

  • (Sep. 18 – 20)Grape Stomp

    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.

    It's still on in 2020. Buy tickets in advance.

  • (Sep. 19 – 20)Vintage Illinois Wine Festival

    Utica, IL

    This festival in northwest Illinois features live music and wine-tasting from 25 Illinois vineyards.

    This year, it's at Carey Memorial Park and is focused on tasting and shopping.

  • (Sep. 19)Apfelfest

    Amana, IA

    In Iowa's Amana Colonies, there's an Apple Sampling Stroll among businesses, a Vintner's Dinner and music at Millstream Brewery.

  • (Sep. 26 – 27)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. 26 – Oct 4)Fermentation Fest

    Sauk City, WI

    This fest in the scenic hills of southwest Wisconsin is not only about pickles and sourdough bread but also cheese, chocolate, beer and wine. There are classes, tastings and the 50-mile Farm/Art DTour, punctuated by art installations.

    This year, the self-guided Farm/Art DTour is still on. There will also be a Food Chain marketplace of food, art and ideas at Witwen Park & Campground, between Plain and Prairie du Sac.

  • (Sep. 26)Art and Artists Celebration

    Taylors Falls, MN

    The 43-acre Franconia Sculpture Park is holding its annual celebration, with bands, food trucks and sculpture tours, as well as the grand opening of its Franconia Commons Building, which includes an art gallery, gift shop and cafe with patio. 

    It's at the intersection of U.S. 8 and Minnesota 95, between Shafer and Taylors Falls.

  • (Sep. 26 – Oct 11)Virtual Doors Open Milwaukee

    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.

    This year, the event is virtual.

  • (Sep. 26)Greenway Glow Arts Festival

    Minneapolis, MN

    This festival along the 5-mile-long Midtown Greenway bicycle trail includes a puppet parade, live performances, art installations and craft beer. It's from 3 to 9 p.m.


  • (Oct. 3)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.

  • (Oct. 3)Fall Village Market

    Mount Horeb, WI

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

    Tickets are $5 and available for time slots until 5 p.m.

  • (Oct. 4)Latino Heritage Virtual 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. 5 – 11)Virtual 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.

    This year, events and readings are online.

  • (Oct. 9 – 11)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.

  • (Oct. 9 – 11)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.

    This year, the carnival and art show are canceled, but there will be a scarecrow stroll, drive-in concert, scavenger hunt, pumpkin carver and items to purchase, such as Scarecrow in a Box.

  • (Oct. 9 – 11)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.


  • (Oct. 10 – 11)Oktoberfest

    Lake Geneva, WI

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

  • (Oct. 10)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. 14 – 25)Chicago International Film Festival

    Chicago, IL

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

  • (Oct. 15 – 17)Wisconsin Virtual Book Festival

    Madison, WI

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

  • (Oct. 15 – 29)Virtual Milwaukee Film Festival

    Milwaukee, WI

    Stream more than 200 films from around the globe.

  • (Oct. 16 – 18)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.

  • (Oct. 16 – Nov 1)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.

    This year, all of the tours will be outdoors or online.

  • (Oct. 17)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.



  • (Oct. 17)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.

  • (Oct. 24 – 31)Halloween

    Anoka, MN

    This town, just north of Minneapolis, calls itself the Halloween Capital of the World. Festivities include a house-decorating contest Oct. 29-30, with results viewable from cars, and a Grande Day Parade  11 a.m. to 3 p.m. Oct. 31, with the parade stationary and viewers in cars.

  • (Oct. 24 – 25)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.

  • (Oct. 24 – 25)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.

  • (Oct. 25)Great Pumpkin Halloween Celebration

    St. Paul, MN

    The Landmark Center in Rice Park hosts this free party for kids of all ages. Admission is by reservation with timed entry.

  • (Oct. 30 – 31)Witching Hour Festival

    Iowa City, IA

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

  • (Oct. 30 – 31)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.

  • (Oct. 31)Arts in the Dark Halloween parade

    Chicago, IL

    This year, the "parade'' will be stationary, and spectators will view it by driving by its stations in Washington Park. It's free, but reservations are required to attend, at noon, 1 p.m. and 2 p.m. slots.



  • (Nov. 6 – 8)Virtual Art Attack

    Minneapolis, MN

    In the northeast arts district, 350 artists open their studios and offer demonstrations and workshops. It's virtual this year.

  • (Nov. 10)Beacon lighting at Split Rock Lighthouse

    Beaver Bay, MN

    This event, which commemorates the 1975 sinking of the ore freighter with 29 men, is the only time the public can see the interior of the light tower when the beacon is lighted.

    In 2020, the ceremony is virtual. The beacon will be lighted, and spectators casn see it from the state park.

  • (Nov. 14 – 15)Virtual Art on the Prairie

    Perry, IA

    This free festival northwest of Des Moines showcases more than 100 Iowa artists, poets and musicians in seven venues, including the Hotel Pattee, in the downtown historic and cultural district. There will also be children's activities.

    This year, it's virtual.

  • (Nov. 20 – 22)Outdoor Adventure Expo

    Minneapolis, MN

    The expo at the Midwest Mountaineering store on the West Bank includes dozens of speakers and seminars about skiing, sled-dog racing and ice-climbing as well as camping, backpacking and other year-round adventures.

    Presentations are virtual in 2020, given Nov. 6-25.

  • (Nov. 20 – 22)Winterer's Gathering

    Grand Marais, MN

    There's a tent encampment, winter skills seminars, Arctic film festival and chili feed at the North House Folk School.

    It's mostly virtual in 2020.