Falling For Wisconsin: An Autumn Guide

As long, warm summer days get noticeably shorter and cooler, there’s a certain magic that sweeps across Wisconsin. From the north to the south, brilliant shades of red, orange, and gold spread. Small towns come alive with harvest festivals, apple-picking orchards, and pumpkin patches.

Fall Foliage

The state’s diverse landscape ranges from the National Forests in the north to the rolling land and bluffs of the Driftless Area and the Mississippi Bluffs. There is no shortage of scenic drives and hikes.

Ideal times to see regional colors:

Late September: Northern Wisconsin typically peaks first, with maples blazing crimson next to dark green evergreens.

Early To Mid-October: Central Wisconsin from Wausau to the Wisconsin Dells reaches its peak.

Mid to Late October: Southern Wisconsin, including Milwaukee, Madison, and Kettle Moraine, shows off its colors.

Leaf-Peeping Recommendations:

Door County: The peninsula’s winding roads, charming villages, and shoreline bluffs make it one of Wisconsin’s most iconic fall destinations. Toward the tip of the peninsula, Highway 42 curves and dips through the trees. Hike Death’s Door Bluff, where the sheer cliff divides the colorful trees from the turquoise waters on sunny days.

Kettle Moraine State Forest: A 115-mile scenic drive through the glacially carved hills of Kettle Moraine State Forest is beautiful.

Devil’s Lake State Park: Hike the Balanced Rock Trail for panoramic views of the quartzite bluffs framed in gold.

Chequamegon-Nicolet National Forest: For a true Northwoods immersion, there are endless stretches of aspen, maple, and birch.

The Great River Road: Follow the winding Mississippi River along the western border of Wisconsin for stunning bluffs and river valleys painted in fall colors. Make sure you count as many eagles as you see! There are a few.

Harvest Season

Fall in Wisconsin has more to offer than just stunning foliage. It’s also when we celebrate the harvest. Much of Wisconsin is agricultural, and we celebrate that heritage. An interesting fact: when Wisconsin was settled, almost every house had an apple tree or more, because apples were so hardy and could be stored through the winterh the winter months in cellars. They thrive in the colder climates of northern Wisconsin.

Apple Orchards and Pumpkin Patches

Wisconsin’s orchards offer the full autumn experience: apple picking, hayrides, cider donuts, corn mazes, and lots of other tasty treats.

Apple Holler (Sturtevant): Near the border with Illinois, on the eastern side of the state, this orchard is very popular with families from both the Milwaukee and Northern Chicago areas. You can’t go wrong with any type of apple, in my opinion, depending on whether you’re looking for good eating apples or baking apples. But try their ZestStar apples for eating! Make sure you pick the ones that are more red than green.

Elegant Farmer (Mukwonago): Famous for its award-winning apple pie baked in a paper bag. It’s a little farther north and west of the border. 

Appleberry Farms: Located near Madison, it’s a favorite for Dane County families looking for apple or berry picking. Check out their website for live music!

Cranberry Country

Did you know? Wisconsin produces more than 60% of the nation’s cranberries. Areas in central Wisconsin like Warrens and Wisconsin Rapids harvest cranberries in late September and early October. During this time, the bogs are flooded and become surreal red seas of floating berries. Warren’s Cranberry Festival, in September, draws over 100,000 visitors, making it one of the largest arts and crafts festivals in the Midwest.

Fall Festivals and Events

Oktoberfest in La Crosse: Featuring the traditional “Festmaster” greeting, polka music, and plenty of Gemütlichkeit, it is one of the largest Oktoberfest celebrations in the Midwest.

Milwaukee’s Oktoberfest and German Fest Events: Milwaukee has a deep German heritage, and during the fall months it is on full display. If you’re in the mood for beer, German food including those giant pretzels, and music, this is a good Oktoberfest to go to.

Bayfield Apple Festival: If you’re in northern Wisconsin, this Apple Festival is picturesque against the Lake Superior backdrop.

Honestly, every little town has a fall or autumn festival. Half the fun is going on a drive and pleasantly being surprised by these cute celebrations.

Outdoor Adventuring

The bugs are gone, the humidity has lifted, and the colors are prime. Fall is an excellent time to get outside before winter hits.

Hiking

Ice Age Trail: Spanning 1,200 miles across the state of Wisconsin, the southern segments are spectacular in fall. If you want to pick up a physical map (not all segments directly connect or may be connected by roadways), stop by the headquarters in Cross Plains.

Apostle Islands National Lakeshore: Hike the lakeshore trails near Bayfield for views of Lake Superior framed in autumn color.

Perrot State Park and Trempealeau Mountain: The bluffs of The Driftless Area offer stunning and dramatic overlooks of the Mississippi River valley and face west. They’re excellent for watching the sunset.

Rib Mountain State Park: Located in Wausau, this hill is surrounded by flat areas, and you can see for miles; in the fall, it looks like you’re looking out over patchwork quilts.

Biking

The Elroy-Sparta Trail, was one of my favorite trails growing up. It is one of the oldest rail-trails in the nation and passes through three historic train tunnels. The Bearskin Trail in the Northwoods is another gem during autumn.

Cozy Autumn Food and Drink

Who doesn’t love fall flavors? You’d be hard-pressed to drive through the University of Wisconsin or the neighborhoods surrounding Lambeau Field and not smell grilled bratwurst, onions, and kraut on game day. But there’s so much more to fall cooking.

Apple Cider: Do you like it cold or hot? I honestly can’t decide! Apple cider is one of my favorite fall treats. And if you add a little bourbon or Fireball to it, it’s a delicious adult beverage when the evenings get nippy.

Stuffed Acorn Squash: Halved, gutted, brushed with olive oil, and roasted inside-out for 25 minutes at 400° F. Then sauté the Italian sausage (pre-cooked), spinach, onion, celery, and maybe some chunked apple while that’s baking. Then stuff the squash halves and top with Parmesan cheese, and pop them back in the oven to bake till the cheese melts. 

Apple and Pumpkin Pie: Or basically anything baked with these two is delicious. But first, butter or lard in your pie crust? I must confess I struggle with processing gluten, so luckily for my waistband, I don’t indulge unless it’s baked gf. I have fond memories of all the bakeries growing up, though pre-stomach pain. 

Chili and Soup: It’s so simple. I love to eat chili and soups in the fall. Throw whatever you want that tastes good together in a pot and let it cook. Yum. Of course, this is when chili cook-offs happen too!

Old Fashioneds: You know what I’m talking about if you’re from Wisconsin. Brandy Old Fashioneds, although you don’t have to twist my arm too hard to substitute bourbon in. Muddle cherries and oranges in a rocks glass traditionally with a cube of sugar (I like a little bit of maple syrup, the real stuff), add the liquor, then add your choice of sour or sweet (Squirt or 7up) as the mixer. Or skip the mixer. I usually do. Mix and serve with a half orange wheel and a cherry as a garnish. They’re good all year round. But so good in the fall.

Game Day

This day is taken very seriously. You can’t overlook the Packers. The green and gold is everywhere. On game day, people show up in the parking lot without tickets to the game just to tailgate and listen to the game. It’s pure Wisconsin. And even if you can’t score tickets, it’s worth it. If you are lucky enough to get tickets, the stadium is a wonderful place to be on a Sunday, especially if they’re winning.

In Closing Thoughts

Check the Wisconsin Department of Tourism’s fall color report if the foliage is high on your list. Dress in layers; the days can get pretty warm, but the mornings and evenings become much cooler. Book your stay in advance. You aren’t the only one who thinks fall is amazing, and don’t skip the small towns; you never know what you’re going to find.

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