Skip busy and bustling peak-season crowds and enjoy Wisconsin’s early-fall fun, including cranberries galore, corn mazes, and other autumn adventures.
Sweater weather season is nearly upon us (or at least cooler mornings that turn into sun-warmed afternoons), which means it’s time for all the autumn adventures. And even though October and November have their own fall holidays, September brings many unsung opportunities for just as much fall fun.
From incredible foliage turning warm hues right before your eyes to traditional Highland games, corn mazes, and more, there are plenty of enjoyable early-fall activities to enjoy around Wisconsin before peak season crowds rush in.
1. Wisconsin Highland Games
Where: 1000 Northview Rd., Waukesha | When: September 4, 5, and 6 – hours vary
Kick off the beginning of fall in Wisconsin with a little fun from far, far away. The Highland Games are a Scottish tradition celebrating Celtic culture, including physical feats, music, and dancing, and we’re lucky enough to get a taste back here in the Midwest.
Although we don’t have highlands here, the Wisconsin Highland Games in Waukesha feature events similar to the original games, like battle axe and knife throwing, Highland dancing, and even a longbow tournament. The festivities wouldn’t be complete without food and live music. The Opening Ceremonies on Friday are free for all to attend and steeped in tradition; on the other two days, tickets are $21 per day.
2. Sunflower Festival at Appleland
Where: 4177 Highway 57, Fredonia | When: September 5 and 6 from 10 a.m. to 4 p.m.
The very beginning of fall marks the last few moments of sunflower season, so naturally, the Sunflower Festival at Appleland Farm Market happens the very first weekend in September.
This family-owned apple orchard has been in the family for three generations and is committed to creating wonderful memories for all their visitors. In addition to the beautiful glow of the sunflowers, you can also find ‘U-pick’ apples (Honeycrisp during this opening weekend), live music, and tasty food.
3. Treinen Farm Corn Maze Preview Weekend
Where: W12420 WI Trunk 60, Lodi | When: September 5, 6, and 7 from 10 a.m. to 7 p.m.
Described as “Wisconsin’s Favorite Corn Maze and Pumpkin Patch,” Treinen Farm is the place to be early this fall. The corn mazes here aren’t just a fun fall activity—they’re works of art. The designs are intricate, the twists and turns are complex, and you’ll spend hours exploring and escaping the maze.
While the main season kicks off on September 19, you can beat the crowds and chaos by picking up tickets to the special preview weekend on September 5, 6, and 7. The farm isn’t limited to fantastical corn mazes—there is also a pumpkin patch and many other fun fall activities.
4. Fall Food Truck Friday
Where: 6501 W National Ave, West Allis | When: Friday, September 11 from 5 p.m. to 8 p.m.
The West Allis Farmers Market will be open throughout September (18 market days), but for one day only—Friday, September 11—it will host a Food Truck Friday and Mini Market.
Over 18 food trucks will line the market from 5 p.m. to 8 p.m. and feature all sorts of tasty treats—from appetizers and the usual suspects (like tacos and pizza) to craft beer. There is something for everyone. A visit to this market is a fantastic way to kick off Friday this fall.
5. Warrens Cranberry Festival
Where: 402 Pine St, Warrens | When: September 25, 26, and 27 (hours vary; full schedule here)
In Wisconsin, cranberries are huge—so huge, in fact, that there are several festivals throughout the fall celebrating them. But one of the best-known and largest is Warrens Cranberry Festival.
Of course, you can find all things cranberry at the fest, but you can also enjoy breakfast kicking off the events at 6 a.m. (complete with cranberry syrup). There are also arts and crafts vendors, marsh-walking tours, and so much more. On Sunday, there’s even a cranberry parade to wrap up the weekend.
6. Apple picking at Apple Holler Family Farm
Where: 5006 South Sylvania Ave, Sturtevant | When: Daily 8:30 a.m. to 4 p.m.
There’s nothing like apple picking to get you in the fall mood. Throughout Wisconsin, there are several hundred apple orchards available for pick-your-own apples. One of the fan favorites that visitors rave about again and again is Apple Holler Family Farm in the southeast corner of the state.
Apple picking is only one of many early fall activities you’ll find at the farm—it’s easy to make an entire day of it. You can also enjoy the farm store and stock up on all your apple favorites and tasty treats, or grab a bite at the restaurant, which serves breakfast, lunch, and dinner.
7. Fall classics cooking class
Where: Milwaukee Public Market, 400 N. Water St, Milwaukee | When: October 6, 5:30 p.m.
Kicking off fall with cozy cooking in the kitchen is a fantastic way to welcome in autumn. If you aren’t sure where to start, take a trip down to the Third Ward and stop by Milwaukee Public Market to check out the cooking classes they offer.
On October 6, you can get a ticket to the Fall Market (Demo), where delicious comfort foods are on the menu, including hot honey Brussels sprouts, sugared cranberries, butternut squash risotto, smashed crispy WI potatoes, and French apple cake. The class is open to 35 people—if you’re interested, register ASAP.
8. Devils Lake State Park hiking
Where: S5975 Park Rd, Baraboo | When: Daily from 6 a.m. to 11 p.m.
There is nothing like a crisp fall breeze during a hike or walk through one of Wisconsin’s many state parks and trails. Early fall is the perfect time for a stroll—it isn’t too hot, and snow hasn’t made a muddy mess of the ground.
One of the best views, a must-visit for nature enthusiasts of all kinds, is Devils Lake State Park. With 16 trails available (including easy, medium, and more difficult trails), everyone will enjoy the fresh air and magical surroundings. The fall foliage is breathtaking, just starting to turn all shades of yellow, orange, and red—really, it’s so gorgeous it doesn’t even look real.
