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30 Most Amazing Fall Festivals in Wisconsin (2023)

A guide to the best fall festivals in Wisconsin in September and October, with Apple Festivals, Cranberry, and other fall fests in Wisconsin

Are you looking for a vibrant and lively way to spend your autumn? If so, start planning to travel Wisconsin today!

As the days get shorter and the leaves begin to fall, Wisconsin celebrates the change of season with hundreds of charming fall festivals in Wisconsin offering something special for everyone.

From pumpkin-picking at family farms in Sturgeon Bay to cheering on floats at one of Appleton’s classic parades, Wisconsin in fall has it all.

Here you can experience breathtaking views, unique cuisines, and amazing activities that will take your breath away this season.

Whether it’s making memories with friends or gaining a deeper appreciation for nature – no matter what brings you here – Wisconsin is sure to surpass all expectations during its wonderful Fall Festivals.

a field in wisconsin in fall
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Overview: Top 5 Fall Festivals in Wisconsin

  • Jack O’ Lantern Days – Fish Creek
  • Warrens Cranberry Festival “Cranfest” – Warrens
  • Milwaukee Oktoberfest – Milwaukee
  • Apple Festival – Bayfield
  • Sister Bay Fall Fest – Sister Bay

What is a fall festival?

A fall festival is a celebration of the arrival of fall and of the local harvests.

Traditional fall festivals involve sampling of local food and drink, flea markets, games, and famously silly contests, as well as live music and other entertainment.

Not all fall festivals are the same!

Many follow the Oktoberfest theme, with authentic German food, beer, and polka dancing, among other attractions.

Wisconsin is also home to harvest-specific celebrations, such as apple and cranberry festivals.

Fall festivals are not unique to Wisconsin, but they definitely have a particularly festive vibe here.

This is especially true for small-town Wisconsin fall festivals, which are held in quaint, picturesque little villages and towns.

There are many fantastic Wisconsin festivals in October no matter where you are that the whole family can enjoy.

In fact, Wisconsin has some of the best Midwest fall festivals!

So, check out the best fall festivals in Wisconsin, as well as fun fall events in Wisconsin for you to attend and enjoy this fall season.

Best Fall Festivals in Wisconsin

1. Pumpkin Patch Festival – Egg Harbor

october events in wisconsin, couple and baby at a pumpkin patch in Wisconsin
Pumpkin Patch in Door County, Wisconsin

About 60 miles north of Green Bay in northern Wisconsin, the village of Egg Harbor hosts an annual weekend Pumpkin Patch Festival.

This festivals is one of the best fall festivals in Wisconsin, and people come from all over Door County!

The festival features food, live music, arts and crafts vendors, auctions, raffles, carnival rides, scarecrow displays, and plenty of other fun and quirky activities for the whole family.

Kids will be particularly thrilled with the magician and the storyteller who regularly visit this festival.

Although Egg Harbor is tiny, reaching just over 200 in total population, there’s plenty to do here beyond the fall festival.

There is a golf course and an orchard nearby that you can explore.

On the other side of the peninsula, just a 20 minute drive away, you’ll find the beautiful Moonlight Bay Bedrock Beach State Natural Area, and the Baileys Harbor Ridges Park recreational park.

Don’t forget to visit nearby Green Bay and check out some of the best things to do in Green Bay in the winter!

There are plenty of fun Green Bay fall activities to enjoy!

The Door County region has some of the best resorts in Northern Wisconsin to ensure your fall stay is amazing.

Book the best tours in Door County

2. Sister Bay Fall Fest – Sister Bay

Best Fall Festivals in October in Wisconsin, View of Sister Bay Beach and restaurants
Sister Bay in the early fall

Sister Bay is a small village in Door County that has some of the best things to do in Door County in October.

Each October, for one weekend the little community becomes a vibrant hub of fall-related activities.

The Sister Bay fall Fest, Wisconsin has over 70 years of tradition and offers a series of activities and concerts.

Past events include a raffle, a classic car show, a customary parade along the Downtown Bay Shore Drive, and lots of games and family fun. 

There is also a regular arts and crafts show where you can buy souvenirs and unique artwork handmade by local artists.

Several music venues (both indoor and outdoor) are prepared for the occasion, with live bands performing day and night.

Of course, food is also a major part of the festival, with a pancake breakfast on Saturday, a fish boil at the local Fire Station, and endless stalls selling beer and authentic Wisconsin delicacies. 

The area is also great for a cabin getaway, which you can do while enjoying a Wisconsin fall festival.

From kayaking to bonfires…it doesn’t get cozier than with a cabin rental in Door County.

If you are staying longer, and you definitely should – make sure to have a look at my guide about the best things to do in Door County.

Book the best cabins in Door County

3. Wine & Harvest Festival – Cedarburg

best Wine & Harvest Festival in Wisconsin, table with multiple bottles of wine

Just over 20 miles north of Milwaukee, the historic town of Cedarburg hosts one of the best Wisconsin festivals in September known as the Wine & Harvest Festival.

It’s thus perfect when looking for day trips from Milwaukee in the fall!

For one weekend, four streets in Cedarburg turn into huge marketplaces, offering everything from local produce to handmade gifts and accessories.

Locally produced cheese, sausage, honey, and syrup are joined by the excellent wines by Cedar Creek Winery, located right there in Cedarburg.

Live music and other entertainment complete the experience, with the Giant Pumpkin Charity Regatta stealing the show every year.

This is definitely one of the best Wisconsin festivals, especially for the over 21s!

If you are looking for fun harvest festivals in Wisconsin to attend, you can’t go wrong with Cedarburg’s Wine & Harvest Festival.

These all make the Wine & Harvest festival to become one among many great Wisconsin vacation ideas and great fall getaways in Wisconsin.

While you’re here, don’t miss out on the other fun things to do in Cedarburg, WI!

Book the coolest AirBnBs in Cedarburg

4. Wo-Zha-Wa Days Fall Festival – Wisconsin Dells

Fun fall events in wisconsin, band playing at the Wo-Zha-Wa Days Fall Festival in Wisconsin Dells
Having fun at the Wo-Zha-Wa Days Fall Festival

If you visit Wisconsin Dells in the fall, you’ll be in for a treat and a very special fall festival in Wisconsin.

In mid-September, the city hosts the uniquely named Wo-Zha-Wa Days fall festival.

In the language of the Ho-Chunk Native American Tribe, “wo-zha-wa” means “to have fun”, and that’s exactly what you can expect if you stay for the festival weekend. 

Food and live entertainment are just the start of what makes this one of the best fall festivals in Wisconsin.

There’s also a huge antique flea market to browse, an arts and crafts fair, and a street carnival including a large parade.

Interestingly, this fall festival also holds the oldest long-distance race in Wisconsin, a half-marathon in the city streets. 

Book cozy cabin rentals in Wisconsin Dells

5. AutumnFest – St. Croix Falls

fun fall festivals in wisconsin, man with guitar singing
Enjoy the live music

For a fun, one-day fall festival, come to the quaint, picturesque town of St. Croix in eastern Wisconsin, right on the border with Minnesota. 

The St. Croix Falls AutumnFest offers everything you can expect from small town fall festivals in Wisconsin.

There is live bluegrass music, food trucks, a farmer’s market and lots of activities for kids.

This festival is the perfect choice for outdoor enthusiasts eager to explore the St. Croix area, with a free self-guided tour of the many surrounding hiking and biking trails. 

Book the top vacation rentals in St.Croix Falls, WI

6. Al & Al’s Oktoberfest – Sheboygan

fall activities in wisconsin, men preparing to do traditional dances at the Al & Al’s Oktoberfest in Sheboygan
At Sheboygan Oktoberfest

The city of Sheboygan on the shore of Lake Michigan is home to a surprising and very different festival; Wisconsin’s answer to the classic Oktoberfest! 

For two days at the beginning of October, you can feel as if you’ve stepped into a small Bavarian town.

Expect live music, authentic German cuisine, folk dancing, thematic events, and of course, lots of German beer and wine. 

To make the experience even more unique, don’t miss the annual Wiener Dog Races taking place during AI & AI’s festival.

It’s one of the most fun things to do in Wisconsin in October and definitely one of the best fall festivals Wisconsin has to offer.

There are lots of other fun fall things to do in Sheboygan, such as museums, historic sites, one of the most unique Wisconsin lighthouses, and even a haunted house!

Check rates for top VRBOs in Sheboygan

7. Madeline Island Fall Fest – La Pointe

fall festival in wisconsin, open piano full of pumpkins

One of the biggest October events in Wisconsin, this series of events takes place in a unique location: Madeline Island, the largest of the Apostle Islands.

The city of La Pointe on Madeline Island turns into a huge playground for kids and adults alike for an entire weekend. 

Alongside your typical fall festival fare, the Madeline Island Fall Fest involves lots of interactive events.

You can learn how to make candles, carve pumpkins, and even make apple cider with locally sourced produce!

Make sure to try the local delicacy known as “waples” which are waffles filled with apple cheesecake and caramel sauce. 

To get to the island and enjoy one of the best festivals in Northern Wisconsin, you’ll need to take a ferry from Bayfield.

Weather permitting, don’t miss the chance to explore the Apostle Islands National Lakeshore’s spectacular sea caves and cliffs. 

Indeed, there are plenty of things to do in Apostle Islands, WI during the fall – or year round!

It’s also the perfect location for romantic getaways in Wisconsin!

Book cozy cabins in the Apostle Islands

8. Jack O’ Lantern Days – Fish Creek

Door County fall festival in wisconsin, Crowd of People Parading in Street
Jack O’ Lantern Days

Fish Creek is home to another Door County fall festival and one of the biggest October events in Wisconsin!

Located about an hour’s drive north from the city of Green Bay, Fish Creek is home to the incredibly popular Jack O’ Lantern Days festival.

Its spooky fall event provides the ultimate Halloween experience, suitable for kids of all ages. 

It’s thus perfect when looking for great weekend trips in Wisconsin.

The Jack O’ Lantern Days offer Halloween-themed games and activities, mask making, a costume contest, a parade, and many other unique and surprising interactive events.

And of course, there is also town-wide trick-or-treating!

Experience a truly unforgettable Halloween at this most unique of Wisconsin October festivals.

If you plan to stay longer, have a look at my list of the prettiest Airbnbs in Door County, or stay at one of the best resorts in Door County!

While you’re in Fish Creek, be sure to check out the Lautenbach’s Orchard Country Market and Winery, one of the best wineries in Door County.

Buy the best road trip guide to Wisconsin

9. Wauktoberfest – Waunakee

events and activities in fall festival in wisconsin, peaople dressed in Bavarian dress standing over table of beers

Another Wisconsin Oktoberfest-style festival, the Wauktoberfest takes place over a whole weekend in September.

The festival is held in the village of Waunakee, just over 12 miles north of Madison, on the other side of Lake Mendota which is one of the best lakes In Wisconsin.

Although it’s in the nearby village of Waunakee, I consider this my favorite fall festival Madison has to offer.

Alongside plenty of German beer and of course, live polka music, the festival offers lots of quirky events and activities.

Helicopter rides, cheese and sauerkraut eating contests, dachshund races, and beer keg races are just some of the surprising attractions you’re in for! 

With so may fun things to do, it’s easy to see why this is one of the top events in Wisconsin in September.

If you’re staying a bit longer, the city of Madison, only 20min drive away, offers all sorts of activities, including museums and a zoo to visit.

The area is also home to the best beaches in Wisconsin which are a perfect setting for romantic fall walks.

Check out tours in Madison here

10. Harvest Fest – Sturgeon Bay

fbest estivals in wisconsin in september, apples being held in shirt at the harvest fest fall wisconsin
Apple picking at the Harvest Fest

Also on the Door Peninsula, the town of Sturgeon Bay hosts a yearly, one-day festival to celebrate the arrival of fall.

This is one of the best harvest festivals in Wisconsin and one of the top things to do in Door County in September.

But the usual festival attractions such as regional food and drink, aren’t all you’ll find at the Sturgeon Bay Harvest Fest.

This fall festival in Wisconsin also involves art shows, stalls showcasing local craftsmanship, and a classic car show comprising over 150 vehicles.

Children’s activities and live entertainment ensure that there’s something to do for the whole family and making it one of the top Door County fall festivals.

Interestingly, the city of Sturgeon Bay is built at the natural end of Lake Michigan’s bay of the same name.

An artificially-built ship canal crosses right through the city, with a steel bridge connecting the two halves.

There is a large maritime museum in Sturgeon Bay, as well as an art gallery and historical museum.

There are also, of course, plenty of opportunities to admire Door County in fall in one of the nearby natural areas.

The area surrounding Sturgeon Bay is home to plenty of hiking trails which are among the best hiking trails in Wisconsin. The perfect activity for a cabin getaway in Door County, WI.

Check out cozy cabins in Door County

11. Great Lakes BrewFest – Racine

best fall festivals in September in wisconsin, Man hand holding a sample glass of beer.
Bottoms up!

The primary theme of this festival is simple: beer! Every year, visitors can sample over 450 different beers, as well as ciders and hard sodas.

There’s also live music and delicious food from local food vendors.

Keep in mind that due to the nature of this event, only those aged 21 and over are allowed to attend!

If you’re looking for the best fall fest Milwaukee has to offer, this is it – although technically it’s in Racine, WI.

Still, the city of Racine, just 20 miles south of Milwaukee, offers plenty of family-friendly attractions.

Between several museums, a gorgeous beach, and a zoo, there are lots to do for visitors of all ages making this one of the best festivals in Wisconsin.

Book cool cabin getaways in Racine

12. Oktoberfest – Cedarburg

Best October festivals in Wisconsin, meal of sausages and potatoes with foamy beer
A delicious feast at Oktoberfest in Cedarburg, WI

Cedarburg sure likes its fall festivals!

Soon after the September Wine & Harvest Festival (#3 on this list) comes the Cedarburg Oktoberfest, another one of the best fall festivals in Wisconsin in October.

To give a feel of a real Oktoberfest celebration, the festival takes place outdoors.

Every year, a huge tent is erected, with tables, stalls, and a wooden dance floor within.

Expect live German folk music, polka, and lots of beer and authentic food.

Alongside other entertainment, there is a recurring live comedy event: the Glockenspiel Show.

Book cool AirBnBs in Cedarburg

13. Milwaukee Oktoberfest – Milwaukee

most popular Milwaukee fall festivals in Wisconsin, spread of german foods and beer
Milwaukee Oktoberfest

A brat-eating contest, a Weiner dog race, and lots of beer, what more could you ask for?

The Oktoberfest is one of the most popular Milwaukee fall festivals, delivering everything expected from a German-style fall celebration, and more!

Alongside live polka music and German food and drink, the Milwaukee Oktoberfest also includes a Miss Oktoberfest contest and a stein-hoisting competition.

While the former probably doesn’t require an explanation, the latter is a traditional German contest of strength.

The idea behind it is simple: contestants must hold up a stein filled with a litre of beer for as long as they can.

Taking place on the Fiserv Forum Plaza in central Milwaukee, this full-weekend event offers lots of entertainment for the whole family.

It’s a must when looking for fall festivals in Wisconsin, especially Milwaukee fall festivals for over-21s!

Unlike many other beer festivals and Oktoberfests, Milwaukee’s is kid-friendly and hence one of the best things to do in Milwaukee in October for families.

Be sure to see all the other unique things to doin Milwaukee while you’re in the city.

Check out my ultimate guide on where to stay in Milwaukee to make the most of your stay.

Since it’s October, if you’re looking for something a little spooky, Milwaukee has two of the most haunted hotels in Wisconsin for the perfect fall trip.

Be sure to come back at the end of the month to enjoy all the fun things to do on Halloween in Milwaukee.

Book the best tours in Milwaukee

14. Octoberfest – Appleton

wisconsin festivals in september, oktoberfest wisconsin fall sausages
Tasty sausages at Octoberfest in Appleton, WI

Appleton, the hometown of Houdini on the northern shore of Lake Winnebago, is the host of the largest party of the year across all of the Fox Cities.

The local Octoberfest draws in more than 100,000 visitors each year! The festival is spread over two days (usually Friday and Saturday).

The first day involves a massive classic car show with over 400 vehicles and live entertainment, as part of an alcohol-free, family-friendly celebration.

The second day features the usual Oktoberfest fare, German beer, authentic food, and live polka music, but on a grand scale.

In 2019, there were over 80 food stalls, 10 alcohol stands, 150 arts and crafts vendors, and more than 20 live bands performing in one day!

While you’re here make sure to check out all the other fun things to do in Appleton.

If you’re staying, and you definitely should, Appleton is home to some of the best spa resorts in Wisconsin.

Book the best vacation rentals in Appleton, WI

15. Audubon Days Fall Family Festival – Mayville

best festivals in wisconsin for kids, girl holding a pumpkin with stickers on it to look carved
Get ready for Halloween at the Audubon Days Fall Family Festival
  • When: 3rd weekend of October
  • Accommodation Options: It’s easiest to just stay in Milwaukee and go to Mayville as a day trip. The Pfister Hotel is a true legend in town and the Schuster B&B is probably the most scenic option. For Airbnb fans, this Historic House is only a short walk from a scenic park and this studio is perfect for budget and solo travellers.

This is one of the best small-town fall festivals in Wisconsin as it’s all about family fun – it’s also been running for over 25 years!

Kid-friendly attractions include a rubber duck race, a petting zoo, children’s crafts, photo booths and more. Just be aware that many of the events cost some money.

Plus lots of food vendors with delicious local delicacies to try! And there are even prizes to be won!

If you are looking for October festivals in Wisconsin, the Audubon Days Festival is perfect for a day out with the family.

Mayville can easily be done as a day trip from Milwaukee.

Book the best cabins in Milwaukee

16. Zoo Brew – Milwaukee

best festivals in wisconsin for adults, toasting at the Zoo Brew festival

One of the best Wisconsin festivals for the adults is Zoo Brew. In fact, alll attendees must be over 21 years of age – no exceptions.

For those looking for adult-only things to do this autumn, this is definitely one of the best fall festivals in Wisconsin in October.

Those attending Zoo Brew will get to sample brews from dozens of local (and nearby) brewers.

There will also be local food vendors in attendance to make sure you aren’t drinking on an empty stomach!

This festival is one of the most unique things to do in Milwaukee in October, and definitely one of the best fall festivals Wisconsin has to offer for an adult-only night out.

Book the best food tours in Milwaukee

17. Maple Fall Fest – Marshfield

best, events in wisconsin in september, cup of maple syrup

Held annually at the Wildwood Park & Zoo, the Maple Fall Festival is one of the most popular Wisconsin festivals in September.

This large festival features over 100 Wisconsin vendors selling food, crafts, and experiences.

As one of the best family-friendly fall events Wisconsin has to offer it’s no surprise they have lots of great activities for the whole family.

Some of the top things to do here are visit the petting zoo with the kids or take part in one of the dance competitions.

Of course, it wouldn’t be a Maple Fall Fest without sampling some of the delicious maple syrup products available!

While in Marshfield, don’t forget to visit Escape Room Marshfield. It’s one of the best escape rooms in Wisconsin!

Buy the best itinerary to Wisconsin

18. Big Water Film Festival – Ashland

festivals in northern wisconsin, group of people with popcorn watching a film in a cinema
Grab your popcorn for the Big Water Film Festival

If you’re looking for unique Northern Wisconsin festivals, look no further than the Big Water Film Festival.

The Big Water Film Festival is one of the best fall events Wisconsin has to offer those looking for something a little different.

At Big Water instead of sampling tasty treats, you’ll get to sample carefully selected films before anyone else!

This film festival might not bring in the same kind of names as TIFF or Cannes, but you’ll still get to enjoy high-quality local talent you might otherwise have never heard of!

And if you’re a filmmaker yourself, you could even consider submitting your own work for consideration.

While up north, I highly recommend checking out some of the amazing things to do on the Apostle Islands, which are nearby.

Book the best cabins in Northern Wisconsin

19. Greendale Oktoberfest – Greendale

best fall events in wisconsin for kids, arts and crafts with pumpkins
Fall arts & crafts at the Greendale Oktoberfest

This is another excellent family-friendly event full of fun fall festival attractions like hay rides and pumpkin bowling.

There are also plenty of opportunities to make arts and crafts, or get your faces painted in festive designs.

Local food vendors have many delicious Wisconsin favorites available, and several local breweries also provide alcoholic options.

Despite what the name suggest, the Greendale Oktoberfest is actually one of the best festivals in Wisconsin in September – NOT October!

Although it does change year to year, the festival is typically head near the end of September.

Book the best tours in Milwaukee

20. Harvest Festival – West Allis

fall festivals in Milwaukee, Close up shot of musician holding an electric guitar with drummer standing close behind

One of the most iconic Midwest fall festivals is the Harvest Festival that West Allis puts on each year.

The Harvest Festival is fun for the whole family with free live entertainment from local bands and entertainers going all day – including the annual Lumberjack show.

There are also plenty of activities and rides for the whole family to enjoy throughout the weekend.

One of my favorites is going pumpkin bowling, but you can also try out other activities like making your own scarecrow or the giant slide.

This is one of the best fall festivals in Milwaukee and the surrounding area for families.

Book the best vacation rentals in Milwaukee, WI

21. Blue River Autumn Fest – Blue River

Fun events in Wisconsin in October, Man cutting into a pumpkin during a pumpkin carving event while a young girl watches closely
  • When: 3rd weekend of August
  • Accommodation Options: Renting an Airbnb is the best option to visit the festival. Have a look at the Hill House is one of the prettiest options in town, or the Redbird Ridge Cabin or the Rustic Luxury

If you are looking for fall festivals in Wisconsin that are earlier in the season, the Blue River Autumn Fest is perfect.

Hosted annually on the 3rd weekend of August in the Central Wisconsin village of Blue River, this autumn festival is the ideal way to kick off the season.

Attendees can enjoy a range of typical Wisconsin fall activities for the whole family, including tractor pulls, horseshoe pitching, and some classic ball games.

The festive weekend always ends with a parade on Sunday to celebrate the start of autumn.

For fall festivals in Wisconsin that are a bit more lowkey, you can’t go wrong with this one.

Buy the Like a Local Guide to Wisconsin

22. Wausaukee Fall Fest – Wausaukee

fall festivals Northern Wisconsin, Close up shot of child having their face painted in tiger colors and patterns
  • When: 1st Saturday of October
  • Accommodation Options: The Lauerman House Inn has the best reviews in Marinette and the Country Inn & Suites by Radisson comes with a pool and hot tub. Marinette County is perfect for a cabin getaway, have a look at this Cozy Cabin on the Menominee or this homey cottage in Crivitz.

One of the best events in Wisconsin in October is the Wausaukee Fall Fest in Marinette County.

This annual event invites regional crafters and vendors to take part for a small donation, which in turn allows them to offer free admission to attendees.

With over 100 crafters and vendors offering their wares, you’ll find plenty to enjoy, including tasty food (like local fudge!) and refreshments.

There are also free activities for adults and kids alike, such as face painting and the popular horse-drawn wagon rides.

Of course, this wouldn’t be one of the top fall festivals Northern Wisconsin offers without the promise of live music throughout the day.

Book the best cabin rentals in Northern Wisconsin

Best Apple Festivals in Wisconsin

23. Apple Festival – Bayfield

small town fall festivals, caramelized apples at the Apple Festival in Bayfield, Wisconsin
Yummy caramelized apples at the Apple Festival in Bayfield, WI

Taking place annually for almost 60 years now, the Bayfield Apple Festival is a celebration of fall, nature, and agriculture.

The local orchards and wineries are open to visitors, and unique events take place during the entire weekend.

Of course, this makes it one of my favorite fall weekend getaways in Wisconsin!

In addition to sampling local produce, including jellies, syrups, and wine, you can browse countless arts and crafts stalls, and enjoy live music at this famous apple festival in Wisconsin.

There are plenty of other fun events like the annual apple peeling contest to attend and an authentic Wisconsin fish fry.

At the end of the festival, there is a huge parade which features a band with 400 members!

Bayfield is also perfect for a romantic getaway as it has one of the best romantic hotels in Wisconsin, and is nearby to some of the best waterfalls in Northern Wisconsin.

Buy the best Wisconsin Road Trip Itinerary

24. Fall Fun Fest & Cider Pressing Party – Washington Island

one of the best fall festival in Wisconsin, images of cider making and apples
Fall Fun Fest & Cider Pressing Party on Washington Island, WI

Washington is a fairly large island on Lake Michigan.

Since 1987, its Farm Museum has been holding an annual fall festival where you can press your own cider using the museum’s historic equipment.

You can bring your own apples to press or buy local ones on-site.

Every year, there’s live entertainment, games, and activities for kids, and free horse and wagon rides.

Local cider and authentic Wisconsin cuisine are available too, including brats, chili, cookies, and caramel apples.

It’s easy to see why this is one of the best things to do in Northern Wisconsin!

Washington Island can be reached by ferry, departing from the town of Northport at the tip of the Door Peninsula.

If you stay a while longer, you can explore Washington’s many natural areas, museums, and historic sites.

All this makes Washington Island a great place to vacation in Wisconsin.

Washington Island is also just perfect for a cozy cabin getaway and has some of the best romantic cabins in Wisconsin.

While you’re on Washington Island, you could also pop into Nelsen’s Hall.

This haunted watering hole is one of the most haunted places in Wisconsin!

Book cozy cabins on Washington Island

25. Gays Mills Applefest – Gays Mills

Best Apple Festivals in Wisconsin, sign for Gays Mills Applefest
Welcome to Gay Mills!
  • When: 4th week of September
  • Accommodation Options: Renting an Airbnb is the best option to visit the festival. Have a look at the Hill House is one of the prettiest options in town, or the Redbird Ridge Cabin or the Rustic Luxury

For full immersion in authentic fall harvest celebrations, visit the Mills Apple Festival at the end of September.

The festivities include live music, dancing, a parade, carnivals, and lots of local food and drink to sample. 

There is also a flea market to visit and many arts and crafts stalls with interactive activities.

You can also spectate live games and sports, including volleyball and basketball tournaments, as well as an old-timey horseshoe pitching contest.

Gays Mills is a small village on the Kickapoo River in southern Wisconsin, about 85 miles northwest of Madison.

If you’re planning on staying overnight, the nearby towns of Boscobel and Soldiers Grove offer hotel accommodations.

For a more rustic experience, rent a cabin in Ferryville on the Mississippi River, only 15 miles away.

Bring the whole family – furry friends included and stay at one of the best pet-friendly cabins in Wisconsin.

26. Hillside Fall Festival

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fall festivals in Southern Wisconsin, Three young children sitting in the back of a cart being pulled by an old man in a tractor through a field of tall crops lined with taller green trees

Another one of my favorite fall festivals near Madison WI is the Hillside Fall Festival, which is all about apples.

This rural fall festival is a lot of fun for kids and anyone who loves apples!

Although free games for the kids and free tractor wagon rides are always available, every year is a little different, so there’s no guarantee of all the activities and vendors available.

However, fun and tasty apple dishes are always a promise at one of the best fall festivals in Southern Wisconsin.

Book the best tours in Madison, WI

Best Cranberry Festivals in Wisconsin

27. Warrens Cranberry Festival “Cranfest” – Warrens

Best Cranberry Festivals in Wisconsin, Flooded Cranberry Marsh with Green Pines in background
Flooded Cranberry Marsh

Cranberry festivals make for popular fall activities in Wisconsin.

The village of Warrens proudly calls itself “Wisconsin’s Cranberry Capital”, so it only makes sense that it would be home to the largest cranberry fall festival in the state!

Located in southwestern Wisconsin, just over 10 miles north of Tomah, Warrens has a population of less than 400 but for one weekend in September, it’s one of the busiest places in the county!

In 2019, Cranfest featured the largest band parade in Wisconsin.

Every year, there are (literally!) thousands of stalls all over the village, with souvenirs, arts and crafts, food and drink, and of course, lots of cranberry-based produce.

The festival also provides an opportunity to take a guided bus tour of the surrounding cranberry marshes, which make for a truly unforgettable sight!

Back in town, there are lots of fun competitions to observe and take part in, including a costume contest, a pie-eating contest, and a scarecrow competition.

While here, make sure to visit the Cranberry Museum, it’s one of the best things to do in central Wisconsin.

Book cool AirBnBs in Warrens

28. Cranberry Fest – Eagle River

unique fall festivals in wisconsin, cranberry bog at eagle river fall festival
Cranberry bog in Eagle River, Wi

Cranberry brats, cranberry baked goods, cranberry beer and wine, cranberry soups,… You can sample all of these and more at the Cranberry Fest in Eagle River, northern Wisconsin.

In addition to all the cranberry-infused delicacies, the festival also offers tours of cranberry marshes, wine tours, a flea market, an arts and crafts show, and plenty of live entertainment.

With more than 40,000 people attending this cranberry festival in Wisconsin annually, this isn’t one to miss!

While you’re in Eagle River, don’t forget to check out the Northwoods Escape Room, one of my favorite escape rooms in Wisconsin!

Book the best cabins in Northern Wisconsin

29. Cranberry Festival – Stone Lake

best small town fall festivals in wisconsin, bowl of cranberries
Cranberry pucking at the Stone Lake Cranberry Festival

The usually quiet little community of Stone Lake in northwestern Wisconsin bursts with life at the beginning of October, as thousands arrive for the annual Cranberry Festival.

Live music, marsh tours, parades, food and drink stalls, and plenty more await cranberry lovers in Stone Lake.

The main festival parade is followed by a recurring event called Krate Derby – Stone Lake takes on crate derby, a live street racing event.

Check cool AirBnBs nearby

30. Cran-A-Rama – Manitowish Waters

Cranberry fall festivals in Wisconsin, Two small blue bowls full of cranberries on wooden table surrounded by more loose cranberries

One of the best cranberry festivals in Wisconsin is the Cran-A-Rama in Manitowish Waters.

Attendees can enjoy cranberry tastings and treats from local vendors, as well as a cranberry count.

There are usually some cranberry crafts available, as well, making this Wisconsin fall festival great fun for the whole family.

Visitors to Manitowish Waters can go on a cranberry marsh tour to learn more about how they are grown and why they’re important to the region.

Don’t miss out on one of the best fall festivals in Wisconsin dedicated to the amazing cranberry!

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Before You Go: Top Tips for your Trip 

Short FAQ about Wisconsin Festivals in Fall

What are the best fall festivals in Wisconsin Dells?

The Wo-Zha-Wa Days Fall Festival and the Dells On Tap Weekends are the best fall festivals in Wisconsin Dells.

What are some of the best places to visit in Wisconsin in Fall?

Stone Lake, Eagle River, and Bayfield are some of the best places to visit in Wisconsin in fall.

What are the best Wisconsin fall fests this year?

Some of the coolest fall festivals in Wisconsin to visit are the Pumpkin Patch Festival in Egg Harbor, Sister Bay Fall Fest in Sister Bay, and Wine & Harvest Festival in Cedarburg.

What are the best fall festivals in Western Wisconsin?

Some of the best Western Wisconsin fall festivals are the Cranberry Festival in Stone Lake, Big Water Film Festival in Ashland, AutumnFest in St. Croix Falls,  the Warrens Cranberry Festival “Cranfest” and the Madeline Island Fall Fest in La Pointe.

What are the best fall festivals in Northern Wisconsin?

Jack O’ Lantern Days in Fish Creek and the Eagle River Cranberry Fest are two of the most popular Northern Wisconsin fall festivals. AutumnFest in St. Croix Falls, Big Water Film Festival in Ashland and the Madeline Island Fall Fest in La Pointe are also great Northern Wisconsin fall festivals.

What are the best fall activities in Wisconsin?

There are many amazing fall festivals in Wisconsin that host a range of fun activities for the whole family, including tractor rides, pumpkin bowling, scarecrow building, and live music.

What are the best fall festivals in the Midwest?

I’m biased and I think the fall festivals in Wisconsin are the best fall festivals in the Midwest. Some of my favorite Wisconsin fall festivals are the Sister Bay Fall Fest, Bayfield Apple Festival, Milwaukee Oktoberfest, and Jack O’ Lantern Days – Fish Creek.

What are the Wisconsin events in October?    

There are many great October events in Wisconsin. I particularly love Jack O’ Lantern Days in Fish Creek, Milwaukee Oktoberfest, Sister Bay Fall Fest, Pumpkin Patch Festival, Cranberry Fest in Eagle River, and the Audubon Days Fall Family Festival in Mayville