MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Great fall festivals

Here are the best of the autumn fests in 2020.

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.

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.

In 2020, many festivals have been canceled, altered or will take place online. Check before you go.

Even in normal years, 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.

Children's Halloween parade.

© Beth Gauper

Children march in a Halloween parade.

Second weekend in September

Virtual 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. 12.

Monarch Festival in 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. Sept. 12.

Virtual World Music Festival in Madison, WI This free festival features music and dance from around the world on the Memorial Union Terrace and, on Saturday, at the Willy Street Fair. It's virtual this year. Sept. 12–13.

Virtual World Music Festival in 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.  Sept. 13.

Apple Festival in Bayfield.

© Beth Gauper

In Bayfield, Apple Festival draws crowds.

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. This year, the parade is drive-through and some events are canceled. Sept. 16–19.

Unplugged & Birch Bark Bash in 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. Sept. 18–19.

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. It's still on in 2020. Buy tickets in advance. Sept. 18–20.

Apfelfest in Amana, IA In Iowa's Amana Colonies, there's an Apple Sampling Stroll among businesses, a Vintner's Dinner and music at Millstream Brewery. Sept. 19.

Vintage Illinois Wine Festival in 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. Sept. 19–20.

Virtual World Music Festival in 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.  Sept. 20.

Fourth weekend of September

Blue Ox Music Festival: Campout in the Pines in Eau Claire, WI This family-friendly acoustic festival is near Eau Claire and features Big Wu, Pistol Whippin Party Penguins, Lindsay Lou and Buffalo Gospel. There's camping onsite. Sept. 25–26.

Art and Artists Celebration in 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. Sept. 26.

Greenway Glow Arts Festival in 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. Sept. 26.

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. 26–27.

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. 26–27.

Fermentation Fest in 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. Sept. 26–Oct. 4.

Virtual 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. This year, the event is virtual. Sept. 26–Oct. 11.

Virtual World Music Festival in 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.  Sept. 27.

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.

First weekend in October

Fermentation Fest in 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. Sept. 26–Oct. 4.

Virtual 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. This year, the event is virtual. Sept. 26–Oct. 11.

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. 3.

Fall Village Market in 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. 3.

Latino Heritage Virtual 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. Oct. 4.

Virtual Iowa City Book Festival in 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. 5–11.

Second weekend of October

Virtual 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. This year, the event is virtual. Sept. 26–Oct. 11.

Virtual Iowa City Book Festival in 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. 5–11.

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. 9–11.

Scarecrow Festival in 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 in Cedarburg, WI This studio tour in eastern Wisconsin includes more than 60 artists in Cedarburg, Grafton, Port Washington, Mequon, Thiensville and Newburg.   Oct. 9–11.

Pipestone Paranormal Weekend in 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. 10.

Oktoberfest in Lake Geneva, WI There will be music, food and free pumpkins on downtown streets. Oct. 10–11.

A float from the La Crosse Oktoberfest parade.

© Beth Gauper

In La Crosse, Oktoberfest stretches across nine days.

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 virtually and at the ChiTown Movies Drive-In in Pilsen. Oct. 14–25.

Wisconsin Virtual Book Festival in Madison, WI This big fest features readings, lectures, book discussions, writing workshops, live interviews and children's events. Oct. 15–17.

Virtual Milwaukee Film Festival in Milwaukee, WI Stream more than 200 films from around the globe. Oct. 15–29.

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. 16–18.

Open House Chicago in 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. 16–Nov. 1.

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. 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. 17.

Laura look-alikes compete in Pepin.

© Beth Gauper

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

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 virtually and at the ChiTown Movies Drive-In in Pilsen. Oct. 14–25.

Virtual Milwaukee Film Festival in Milwaukee, WI Stream more than 200 films from around the globe. Oct. 15–29.

Open House Chicago in 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. 16–Nov. 1.

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. 24–25.

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. 24–25.

Halloween in 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. 24–31.

Great Pumpkin Halloween Celebration in 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. 25.

Cheese Days parade in Monroe.

©

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

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.

Virtual Milwaukee Film Festival in Milwaukee, WI Stream more than 200 films from around the globe. Oct. 15–29.

Open House Chicago in 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. 16–Nov. 1.

Halloween in 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. 24–31.

Witching Hour Festival in Iowa City, IA This festival focuses on the creative processes of musicians, artists, comedians, writers, thinkers, scientists and magicians.  Oct. 30–31.

Zombie Days in 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. 30–31.

Arts in the Dark Halloween parade in 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.   Oct. 31.

Second weekend in November

Virtual Art Attack in Minneapolis, MN In the northeast arts district, 350 artists open their studios and offer demonstrations and workshops. It's virtual this year. Nov. 6–8.

Beacon lighting at Split Rock Lighthouse in 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. 10.

Civil War re-enactors march at Norskedalen.

© Beth Gauper

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

Third weekend in November

Virtual Art on the Prairie in 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. 14–15.

Holiday Fantasy in Lights in Madison, WI The free display in Olin Park is open from dusk to dawn. Nov. 15–Jan. 1.

For more, see Great holiday festivals.


Last updated on November 3, 2020