MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Great fall festivals

Here are the best of the fests in 2014.

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 2015. 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 There's a riverfront fine-arts festival, rodeo and Saturday bike tour in this town, a hour south of the Twin Cities, but don't miss the re-enactments of the famous bank raid. Sept. 9–13.

Pufferbilly Days in Boone, IA This festival in central Iowa, just west of Ames is named for a steam engine and features a spike-driving contest, parachute jumps, mud volleyball and rides on the Boone and Scenic Valley Railroad. A parade is Saturday. Sept. 10–13.

James J. Hill Days in Wayzata, MN The festival in this western suburb of Minneapolis is best known for its Saturday dachshund races, in which more than 100 dogs compete in the hurdles, sprints and sofa jump, followed by a costume contest and smart pet tricks. There's also an arts and crafts fair, water-ski show, kids' carnival and parade at 1 p.m. Sunday on Lake Street. Sept. 11–13.

Indian Summer Festival in Milwaukee, WI This lakefront festival features a powwow, canoe rides, Aztec dancers, lacrosse lessons and fireworks. Sept. 11–13.

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. 11–13.

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. 11–13.

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. 11–13.

World Music Festival in Chicago, IL There will be more than 80 artists performing at more than 30 venues across the city, with some performances free and some ticketed. Sept. 11–22.

Sun Prairie Blues Fest in Sun Prairie, WI There's a whole day of blues at Angell Park in this little town just northeast of Madison. Sept. 12.

Washington County Bluegrass Festival in Lake Elmo, MN Monroe Crossing and other bands will play at this family festival at Lake Elmo Park Reserve, free with $5 vehicle permit. There also will be camping and food vendors. Sept. 12.

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. 12.

Laura Ingalls Wilder Days in Pepin, WI The famous author was born in the bluffs above this Mississippi River town, which celebrates with guided bus tours to the birth site, kids' pioneer games, traditional music and crafts and a Pepin Laura contest that tests knowledge of the "Little House'' books. Sept. 12–13.

Rock Bend Folk Festival in St. Peter, MN This free, easygoing festival in this Minnesota River town's Minnesota Square Park features local favorites The Divers. Sept. 12–13.

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. 13.

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. 13.

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

World Music Festival in Chicago, IL There will be more than 80 artists performing at more than 30 venues across the city, with some performances free and some ticketed. Sept. 11–22.

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 and serves pumpkin ice cream, pancakes and fudge at its festival, which features a 10:30 a.m. Saturday parade. Sept. 16–19.

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. 17–19.

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. 17–20.

Wo-Zha-Wa Days in Wisconsin Dells, WI There's a juried arts and crafts show, street carnival and parade Sunday. Sept. 18–20.

Taste of Traverse City in Traverse City, MI There's a Grub Crawl, a Foodie Film Festival and sampling and chef demonstrations at Taste. Sept. 18–20.

Grape Stomp in Alexandria, MN Carlos Creek Winery hosts this festival, which features a Friday barn dance, "I Love Lucy'' look-alike contests, grape stomps, comedy, music and crafts vendors. Sept. 18–20.

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, hammerschlagen, beer keg race, dachshund dash and Limburger cheese and sauerkraut eating. Sept. 18–20.

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. 19.

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. 19.

International Fall Festival in Eau Claire, WI See the Parade of Nations, an international bazaar and music on the World Stage. Sept. 19.

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. 19.

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. 19–20.

Fall Gathering at the North West Co. Fur Post in 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 an hour north of the Twin Cities. For the kids, there's a bead scramble, candle-dipping and a scavenger hunt. Sept. 19–20.

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. 19–20.

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. 19–20.

Fourth weekend of September

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. 23–27.

Boats and Bluegrass in Winona, MN This family-oriented festival in Prairie Island Park, on the Mississippi River, features disc golf, paddling and airplane rides as well as music. A weekend pass includes camping and canoeing, and kids under 16 are free with an adult ticket. Sept. 24–27.

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. 25–26.

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. 25–27.

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. 25–27.

Fall Festival in Hayward, WI There's an arts and crafts fair, children's games, contests and live music downtown. Sept. 26.

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. 26.

Tour of Historic Galena Homes in Galena, IL Tour five private homes and the History Museum in this picturesque town in northwest Illinois. Sept. 26–27.

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. 26–27.

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. 26–27.

Children's Halloween parade.

© Beth Gauper

Children march in a Halloween parade.

First weekend of 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. Oct. 1–4.

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. 2–4.

Audubon Days in Mayville, WI The festival in this town next to big Horicon Marsh features bed races, a bike tour, rubber-duck race and parade Sunday. Oct. 2–4.

Chain O' Lakes Blues Festival in Waupaca, WI Listen to the blues at the historic Indian Crossing Casino. Oct. 2–3.

Apple Festival in Bayfield, WI It's the 54th year of this big festival on Lake Superior. Highlights include Big Top Chautauqua concerts, Pipes & Drums from Thunder Bay, the lighted Venetian boat parade and the grand parade at 2 p.m. Sunday. Oct. 2–4.

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.

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. 3–4.

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 at 1 p.m. Sunday. Oct. 3–4. Autumn on Parade website

Laura look-alikes compete in Pepin.

© Beth Gauper

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

Second weekend in October

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. 9–11.

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. 9–11.

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, appearances by Carver and other historical figures, spelling bees, live music and an antique vehicles parade at 2 p.m. Sunday. Oct. 10–11.

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. 10–11.

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. 10–11.

Oktoberfest in Cedarburg, WI This festival just north of Milwaukee features music and food plus goofy contests: wife-carrying, sauerkraut-eating, a German spelling bee and a live Glockenspiel show. Oct. 10–11.

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. 10–11.

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. 10–11.

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. 11.

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. 16–18.

Fall Festival in Sister Bay, WI This Door County festival features camel rides, a sloppy joe-eating contest, pumpkin bowling, a pingpong-ball drop and a Saturday parade. Oct. 16–18.

Applefest in Alexandria, MN Enter a pie-eating contest, play garden chess, go on a horse-drawn wagon ride and watch a pumpkin-catapult contest at Carlos Creek Winery. Oct. 17.

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. 17–18.

Fourth weekend of October

BatFest in Batavia, IL This Fox River town hosts a pumpkin roll, Halloween parade, hay rides, costume contest, "Thriller' dances and a haunted quarry. Oct. 24.

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.

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.

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. 31.

Freakfest in Madison, WI This fest along State Street features music on two stages, outdoor horror movies, a costume contest with prizes and much sampling at bars. Oct. 31.

Halloween Parade in Galena, IL The town's annual parade is along Main Street at 6:30 p.m. Oct. 31.

First weekend in November

Veterans Day Parade in Milwaukee, WI It's at 11 a.m. downtown. Nov. 7.

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.

Cheese Days parade in Monroe.

©

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

Second weekend in November

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. 13–22.

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. 14–15.

Third weekend in November

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. 13–22.

Best Christkindlmarket Milwaukee in Milwaukee, WI Mader's Restaurant and Best Place at Historic Pabst Brewery bring this German-style Christmas market to Milwaukee, with storytelling, dancing, cookie-decorating and appearances by Father Christmas. And beer, of course. Nov. 19–22.

Holiday Lights Festival in Milwaukee, WI The season-long lights festival begins with music, tree-lighting and hot chocolate in Red Arrow Park, then moves across the river to Pere Marquette Park for a family fashion show, variety show, fireworks and free tours on the Jingle Bus. Nov. 19.

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. 20.

Outdoor Adventure Expo in 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. Nov. 20–22.

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. 20–22.

Holiday Parade in Milwaukee, WI It'll have floats, giant helium balloon figures, 20 bands and a live Nativity scene with animals. 9:30 a.m. Nov. 21.

Magnificent Mile Lights Festival & Parade in Chicago, IL There will be music and family activities all day on Michigan Avenue, with a lighted parade from Oak Street to Wacker Drive, where fireworks over the Chicago River will follow. Nov. 21.

For more, see Great holiday festivals.


Last updated on January 7, 2015

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