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Our Favorite Fall Activities in the Milwaukee Area

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Milwaukee Living, Local Communities

Fall is officially here, which means it’s about to be primetime for classic fall activities! So grab your favorite flannel, dig out your apple-picking bucket, and get ready to enjoy the perfect weather and amazing fall colors.

1. Visit the Nearest and Newest National Park
Indiana Dunes National Park—which is near Gary, Indiana—received official “national park” status last February. At only 2.5 hours away by car, Indiana Dunes is Wisconsin’s closest national park, and it’s one of the midwestern states’ coolest.

The park is like a sand-filled playground, with huge dunes to gaze up at and climb, narrow winding hiking trails just inches from the water, and several miles of pristine lakeshore on Lake Michigan. Indiana Dunes is also a photographer’s (or an Instagrammer’s) dream—a lesser-known park with other-worldly sand formations, miles of rugged boardwalks, gorgeously green wetlands and forests, water views, wooded trails that meander into the Indiana backwoods, and far fewer visitors than most national parks.


2. Take a Scenic Drive to One of the Area’s Top Fall Spots

It may be a tourist magnet, but Holy Hill in Hubertus, Wisconsin is a popular fall foliage destination for a very good reason. Take the one-hour drive into the countryside; the drive there is as much a treat as the Holy Hill area itself! Once there, park the car and hit a trail—a portion of the Ice Age Trail goes through the area, as do many other trails. Or, just keep exploring the winding roads as you get deeper into the woods.

If you’re looking to make a day of it, try stopping at one of several orchards or apple stands along the backroads. Our favorite is Pine Hill Orchard off State Highway 167, which has picnic tables and a grassy area for lingering. From the huge variety of apples to the perfectly sweet cider to their candy-covered caramel apples (try the Reese’s Pieces!), Pine Hill is a quintessentially Wisconsin apple stand.


3. Attend a High School or College Football Game

If it’s fall time, it’s football time! It can be difficult and very expensive to attend a Packers game in Titletown, and a local game can be just as much fun. Many nearby colleges have club teams, and Madison of course has the Badgers, if you can find tickets. But a high school game—particularly if it’s your former Wisconsin high school—can be an incredibly fun blast from the past.

Dig up your gear with your alma mater’s logo on it, find a Friday night home game to attend, and stock up on hot chocolate before hitting the stands. The excitement of the crowd can be electric, and the players and their plays have just as much heart and soul as the pros.


4. Attend a Farmers Market and See What You Can Cook Up

Farmers markets are at their peak this time of year, which means there’s plenty of hearty produce out there for the taking. Dig up some fall recipes ahead of time or go in blindly, buy what looks good, and see what kind of impromptu concoction you can whip up in the kitchen.

Keep an eye out for seasonal produce that will really get you in the fall mood, such as squash, pumpkin, carrots, potatoes, turnips, sweet potatoes, kale, brussels sprouts, apples, pears, figs, or cranberries.


5. Take a Hike and Do Some Leaf-Gazing

Taking a hike in some nearby woods is a great fall activity with a low barrier to entry. Plus, it gives you an up-close and personal view of the changing leaves and brilliant colors—just be sure to hit up the trails around the first or second week of October for maximum color.

Check out the trails at Lion’s Den Gorge in Grafton, Havenwoods State Forest in north Milwaukee, or the Kettle Moraine State Forest, which traverses several counties in southeast Wisconsin. If you’re short on time or stuck in the city, check out the Oak Leaf Trail, conveniently located by Wimmer Communities Rivershire Apartments, or the woods behind the Urban Ecology Center, just east of the Milwaukee River. Walk for a mere 10-20 minutes, and you’ll forget you’re even in the city as you take in the kaleidoscope of color.

For Wisconsinites, fall is the last hurrah before the winds and snow of winter start to loom, so now is the time to get outdoors and appreciate the beauty of a seasonal transition.


Each of Wimmer’s communities is within easy driving distance to these idyllic fall activities, but they’re all also located in unique, vibrant, and growing towns around the Milwaukee area. Residents have no shortage of ways to stay entertained no matter the season and no matter which suburb they live in.

Some communities, like Poplar Creek and RiverWalk on the Falls, are located in bustling, faster-paced areas near shopping and restaurants, while others like The Sanctuary or Whitnall Glen offer quieter, more peaceful settings—without sacrificing proximity to highways, business districts, and community amenities.

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