Four Fall Fun Festivals in Wisconsin!

Labor Day has come and gone, September is here. As Wisconsinites we’ll be saying ‘summer is over’, but that’s ok, because deep down inside, my bones are tingling for cool, crisp mornings, vibrant leaves, and all things pumpkin spice. When I was a child, fall and winter were my least favorite seasons of the year due to cold, school and snow, but now that I am an adult, autumn has become my favorite season of them all just for the pure pleasure of cooler weather, coffee, and slowing down. Something changes in the air around here in Wisconsin… people start pulling out their sweaters, mittens and hats to attend fall festivals all around the state. Here is my list of top four fall festivals around Wisconsin.

Warrens Cranberry Festival – Warrens, Wisconsin

It all started roughly 42 years ago when a group of locals sat around a kitchen table and hatched the idea of creating Warrens Cranberry Festival. Half a decade later, it stands as one of Wisconsin’s largest and longest-running fall festivals in the state. What many people may not know is that Warrens CranFest is a nonprofit organization, meaning that money made at Warrens goes right back into the community and Monroe County.

Warrens is a tiny town, around 400 in population, that is nestled between HWY 94 and northeastern Monroe County, the smack-dab middle of cranberry country. You may not know it, but cranberries are Wisconsin’s top producing fruit, generating more than half of the United States’ cranberry needs, which makes cranberries a star of the state.

Working the cranberry marsh

Working the cranberry marsh – Image Credit

Cranberry Overload!

Did I mention how large CranFest is? With over 850+ crafts and arts booths, 350+ booths for antiques and flea market, and even 100+ booths for food, Warrens is huge! Be sure to bring your best walking shoes! When not browsing through crafts and the flea market, head over to check out some of the contests Warrens has to offer. Have a great cranberry recipe? Enter it! Think you have the largest cranberry? Enter it in the ‘Biggest Berry’ contest!

On top of that, CranFest has a parade, and even Cranberry Royalty! You can watch two princesses and a queen become crowned and rewarded for being the best berries. After all that, you can even check out a working cranberry marsh on a tour that runs daily during the festival hours. At the end, you can even pick up fresh cranberries, and cranberry products for purchase.

Warrens Cranberry Festival

Bayfield Apple Festival – Bayfield, Wisconsin

Snuggled on the banks of Lake Superior in northern Wisconsin is the cozy and charming town of Bayfield.  If you have spent any amount of time on any major social media network last year, you may have come across a photo of a man with his dog resting upon his chest in the lake. That photo took place in Bayfield. You may have heard about the famous ‘sea caves‘ of Lake Superior – Bayfield is the main gateway to the Apostle Islands and exploring those caves. Maybe you have even heard about the Edge House? That too is located in Bayfield!

In addition to those perks, Bayfield has a fantastic fall festival which has even been named as “Best Fall Festival in Wisconsin” by Wisconsin Trails Magazine and named “Top Ten Autumn Festivals in North America” by the Society of American Travel Writers. Honing in on celebrating fifty-three years, I can see why it has claimed those famous titles.

Not quite fall, but definitely Bayfield!

Not quite fall, but definitely Bayfield!

All things Apple

Wisconsin has about 300 orchards around the state, producing roughly 60 million pounds of fruit a year! Bayfield wants you to experience the deliciousness of fresh apples during their fall festival. Over 60 orchards and food booths set up shop providing customers with tasty treats such as: apple pies, tortes, sundaes, cider and even a classic Wisconsin delicacy – apple bratwurst!

Another special treat that the Bayfield Apple Fest provides is a grand parade that even features a ‘Mass Band’ – which is a group of about 400 musicians coming together and performing. Be sure to check out the 150 plus arts and crafts booths that set up around town, and to help yourself to another Wisconsin delicacy – a fish boil!

If you need a break from munching on apples and need a bit of fresh air and scenery, during festival hours boat cruises will run to give you a chance to check out the Apostle Island National Lakeshore. If, however, after all that you find yourself still wanting more, be sure to take a tour of one of the 14 local orchards to pick some of your own apples to take home with you.

Bayfield Apple Festival

Wine and Harvest Festival – Cedarburg, Wisconsin

Located about 20 minutes north of Milwaukee, is the very quaint town of Cedarburg, full of rich history and posh storefronts. Unlike the last two festivals celebrating a fruit that Wisconsin has to offer, Cedarburg’s festival is a jubilee of all things fall. Cedarburg’s history began in the late 1800s when settlers came across land near a creek. One man built a house near Cedar Creek and called it Cedarburg, which means ‘house of cedar.’ Afterwards, the town soon became known as Cedarburg, and due to it being on the creek, a water-powered woolen-mill was built.

In 1968 the mill was shut down, and sat vacant for quite some time. Eventually a buyer wanted to buy the building and property, to tear it down and build a gas station. The mayor at the time told the buyer that he would need a ‘demolition permit’, which was not real, but it gave time for another person to come in and save the building. Which is exactly what happened when two men bought the mill and surrounding buildings, to create a restaurant and local galleries.

Later, local store owners came together and started selling goods on the streets during the weekends and that is when Cedarburg’s famous festivals came to life: Strawberry Fest, Wine & Harvest Fest, and even Oktoberfest.

Fall colors along Cedar Creek - Image Credit

Fall colors along Cedar Creek – Image Credit

Wine & Harvest

Cedarburg’s main road, Washington Avenue, is closed off during the fall festival to give room to the 300+ arts and crafts booths. A delectable farmer’s market is there for your produce needs, and down the road you can watch a giant pumpkin weigh-off take place.

Have you ever wondered what they do with those giant pumpkins after they weigh them and are shoved to the side? Have you ever imagined them being turned into a boat? Well, this is exactly what you can see at the Wine and Harvest Festival! Contestants from all over hollow out the massive pumpkins to turn them into a floatable device to race down Cedar Creek. It is probably one of the coolest things I have ever seen.

If you are into carving pumpkins and appreciate good art, Steve Dahlke will be around to carve massive pumpkins into grotesque faces.

Cruise on down to the end of Washington Avenue and you will find yourself by Cedar Creek Winery. Pick up a glass of wine, my favorite being Waterfall Riesling, and get to stomping on some grapes! Or you can even enter yourself into a grape seed spitting contest! Another great winery to check out while you stroll around on Washington Avenue is Chiselled Grape Winery. They recently (for grape vines) planted a vineyard on the Grafton/Cedarburg city line, and their vines are turning four years old.

Wine and Harvest Festival

Sister Bay Fall Festival – Door County, Wisconsin

Fall colors on Washington Island, Door County

Fall colors on Washington Island, Door County

Full of art, folk, and all things rustic, Door County is a uniquely eclectic place to visit. The thumb of Wisconsin, or tail, or whatever you want to call it, known as Door County, is a handful of small towns running along the peninsula of the state.

Death’s Door, (the straight between the peninsula and Washington Island), is where the peninsula earned it’s name after countless ships wrecked on the rocky shores. But Door County isn’t gloomy, not one bit. Actually, it is referred to as the ‘Cape Cod of the Midwest’, and Door County thrives on the summer months between Memorial and Labor Day attracting tourists from Chicago, Milwaukee, Green Bay and even the Twin Cities.

Ephraim is scattered with many homes decorated with white facade, like those in New England, and many come to visit the century old Wilson’s Ice Cream Parlor to pass time with a cool and refreshing treat. Door County even brings a bit of Europe to the state of Wisconsin, as Sister Bay is home to the widely famous Swedish restaurant, Al Johnson’s, where goats are on the roof munching away on sod. The goats have a special way of bringing tourists, but the food has them staying. Be sure to try some Swedish meatballs, and pancakes topped with lingonberries.

What also brings people over to Door County is that it is home to nine different wineries, and two microbreweries and one awesome distillery on Washington Island, Death’s Door Spirits. Door County is the perfect location for cherry orchards so this makes plenty of juice for delicious wines. A couple of my favorite wineries include Door Peninsula, and Stone’s Throw Winery. Be sure to stop for a glass of wine when you make your way through Door County.

Sister Bay Fall Fest

Located north of Egg Harbor and Ephraim is the tiny town of Sister Bay, hugging the coast of the actual bay. Residents of Door County coming together to reward themselves, and celebrate the end of a long and busy summer season, is what kicked off the fall festival.

This year will mark 69 years since it all began and is known as the ‘grandaddy’ of all festivals on the peninsula. Including everything under the Indian Sun, Sister Bay’s Fall Festival has it all: hundreds of arts and crafts booths, plenty of food stands, parades, live bands, and even a Miss Cinderella scholarship coronation. Your eyes can even wander over the smooth metal, shiny vinyl and slick black wheels of the classic car show.

Sister Bay Fall Fest gathers - Image Credit

Sister Bay Fall Fest gathers – Image Credit

Sister Bay Fall Festival

Fall Colors

Door County has come up in a couple different posts we have blogged about in the past. It holds a special place in Andy’s heart. He remembers going up there as a youngster with his parents and siblings, enjoying camping, biking, and long summer nights taking in a drive in movie. It holds a soft spot in my heart as well, because Andy took me up there in October, after we started going out (to the fall festival!), and something about the place took my breath away. We still talk about how fun that trip was.

Door County is a wonderful place to loose yourself in the true colors of the trees that encompass the state of Wisconsin. Roads move with the shorelines, cruising up steep bluffs, coasting down long hills, and trees tightly line the roads. Bursts of orange, blazing red, and tantalizing gold dance with your eyes, pulling you in closer and making you want to stay longer. After you relish in the fun of the festival, take a step back and enjoy what Door County is really about. Go for a drive along the winding roads, go for a hike through one of the many state parks, just remember to let go and enjoy the peacefulness of what the peninsula has to offer.


Washington Island fall colors - Image Credit

Washington Island fall colors – Image Credit

There you have it, a short, but very fun list of fall festivals around the state of Wisconsin that you should be sure to add to your list.

Do you have a favorite fall festival in Wisconsin, or another state? Please comment below to tell us all about it! 


  1. Great information on upcoming festivals! Thanks!

  2. I know it’s not really fall yet, but who could pass up a parade that is led by cows???

    Sept. 19-21 Green County Cheese Days aka Monroe Cheese Fesitval

    Music & Dancing • Yodeling & Alphorns • Three Entertainment Stages • Cheese & Beer • Old-Time Cheesemaking • Cow Milking Contest • Arts & Crafts Fair • Wisconsin’s Only Parade Led by Brown Swiss Cows • Cheese Days Chase • And Much, Much More . . .

    • Andy and I were both in Vegas during this festival, but I am for sure marking it on the calendar for next year! Yodeling, I’m there! :-)

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