MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Great fall festivals

Here are the best of the autumn fests in 2016.

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 2016. 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

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. 7–11.

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. 7–11.

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. 9–11.

Indian Summer Festival in Milwaukee, WI This lakefront festival features a powwow, canoe rides, Aztec dancers, lacrosse lessons and fireworks. Sept. 9–11.

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. 9–11.

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. 9–11.

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. 9–11.

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. Sept. 10.

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 1 p.m. Sunday parade. Sept. 10–11.

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. 11.

Summit Hil 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. Tickets are $25 in advance, $30 on the day of the tour if available. Sept. 11.

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

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. 15–18.

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. 15–18.

Wo-Zha-Wa Days in Wisconsin Dells, WI There's a juried arts and crafts show, street carnival and parade Sunday. Sept. 16–18.

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. 16–18.

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 are cow-milking and cheese sandwich-making contests, yodeling, tours and a big parade Sunday. Sept. 16–18.

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. 16–18.

Riot Fest in Chicago, IL This Douglas Park music festival also features a circus sideshow revue and carnival. Sept. 16–18.

Oktoberfest in Chippewa Falls, WI Meet the Narren, enter a sauerkraut-eating contest, listen to polka and zydeco and watch the daily parade. Sept. 16–18.

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. 17.

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. 17.

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. 17–18.

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. 17–18.

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. 17–18.

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. 17–18.

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. 18.

Fourth weekend of September

Tour of Historic Galena Homes in Galena, IL Tour five private homes and the History Museum in this picturesque town in northwest Illinois. Sept. 23–24.

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. 23–24.

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. 23–24.

Cranberry Festival in Warrens, WI At this huge festival in west-central Wisconsin, there'll be marsh tours, contests and more than 1,300 booths selling antiques, produce and arts and crafts. The big parade is at noon Sunday. Sept. 23–25.

Fall Fest in Cable, WI In the colorful northwest woods, there'll be hay rides, corn maze, a chili cook-off, fish boil, arts and crafts and fireworks. Sept. 23–24.

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 with Alice the owl. Sept. 24.

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. 24–25.

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. 24–25.

Children's Halloween parade.

© Beth Gauper

Children march in a Halloween parade.

First weekend of October

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. 28–Oct. 2.

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. 29–Oct. 2.

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 Sept. 30–Oct. 2.

Art & Big Fork Festival in Evanston, IL This downtown festival features live music and local food, beer, wine and fine art. Sept. 30–Oct. 2.

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. 1.

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. 1.

Big Island Rendezvous and Festival in Albert Lea, MN This southern Minnesota festival is great for families, with more than 1,000 reenactors dancing, demonstrating, competing and pulling visitors back into the fur-trade era. Oct. 1–2.

Fall Heritage Festival in 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. 1–2.

Fall Colors Fine Art & Music Festival in Stillwater, MN This juried arts festival along the banks of the St. Croix River includes music and food vendors. Oct. 1–2.

Fermentation Fest in Reedsburg, 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, performances, the 50-mile Farm/Art DTour, with Roadside Culture Stands, and Bike the DTour. Oct. 1–9.

Laura look-alikes compete in Pepin.

© Beth Gauper

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

Second weekend in October

Fermentation Fest in Reedsburg, 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, performances, the 50-mile Farm/Art DTour, with Roadside Culture Stands, and Bike the DTour. Oct. 1–9.

Chain O' Lakes Blues Festival in Waupaca, WI Listen to the blues at the historic Indian Crossing Casino. Oct. 7–8.

Apple Festival in Bayfield, WI It's the 54th 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. 7–9.

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. 7–9.

Scarecrow Festival in St. Charles, IL There's a big scarecrow contest plus a carnival and the Autumn on the Fox arts show in this town west of Chicago. Oct. 7–9.

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. 8–9.

Fall Festival of the Arts in Red Wing, MN There's a juried show of more than 90 artists downtown, plus music and food. Oct. 8–9.

Civil War Heritage Weekend at Norskedalen in 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. 8–9.

Harvest Fest in New Glarus, WI See old-time artisanry at the Swiss Historical Village, including sausage-stuffing and cheese-making in the 1890s cheese factory. Oct. 9.

Third weekend of October

Autumn Harvest Fest in Wisconsin Dells, WI On Saturday, there are hayrides, pony rides, music and arts and crafts, pumpkin decorating, a straw dig and a scarecrow-stuffing contest. Also on Saturday, chat with brewmasters and sample beer from Wisconsin breweries at Wisconsin Dells on Tap. Oct. 14–16.

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. 14–16.

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. 14–16.

Open House Chicago in Chicago, IL The Chicago Architecture Foundation sponsors this free, behind-the-scenes peek at 150 mansions, clubs, churches, hotels and theaters, including the Lyric Opera, where you can watch a set change and listen to the singers. In Hyde Park, visit Frank Lloyd Wright's Robie House and save the usual $17 cost. Oct. 15–16.

Fourth weekend of October

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. 22–23.

Civil War re-enactors march at Norskedalen.

© Beth Gauper

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

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. 28–30.

UFO Day in 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. 29.

First 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. 4–5.

Veterans Day Parade in Milwaukee, WI It's at 11 a.m. downtown. Nov. 5.

Cheese Days parade in Monroe.

©

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

Second weekend in November

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. Nov. 10.

Trainfest in West Allis, WI The nation's largest operating model railroad show includes more than 60 scenic railroads, clinics for hobbyists and a Kids' Activity Zone with racing trains, face painting and a Circus Train. Nov. 12–13.

Third weekend in November

Festive Friday Eves in Cedarburg, WI Five Christmas celebrations, each with a different theme, at Cedar Creek Settlement, a restored 1864 woolen mill in this historic village just north of Milwaukee. Each features live holiday music, crafts, luminaries, wine-tasting and cookies and cider. Nov. 18.

Winterer's Gathering in Grand Marais, MN There's a tent encampment, winter skills seminars, Arctic film festival and chili feed at the North House Folk School. Nov. 18–20.

Holiday Art Fair in Madison, WI This event at the Museum of Contemporary Art and Overture Center features fine art, music, treats and the Rediscovered Art & Treasures Sale. Nov. 18–20.

Bentleyville Tour of Lights in Duluth, MN Tour the retro-cool lighted decorations in Bayfront Festival Park, including a tree that dances to music, Dinosaurland and Penguin Park. Visit with Santa and Mrs. Claus and enjoy popcorn, roasted marshmallows, cookies and hot chocolate. Everything is free, but bring one or more non-perishable food items (and/or cash) to donate. Nov. 19–Dec. 25.

For more, see Great holiday festivals.






Last updated on January 22, 2016

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