Milwaukee Fall Bucket List

It’s officially Fall here in Milwaukee, and I couldn’t be happier! Waking up to cool, crisp mornings, seeing the colors change in the trees, and enjoying all of the seasonal flavors really put me in a good mood.

Fall in Wisconsin is probably my favorite time of year. Yes, Summer is great, but there is a slower pace to fall. A cozy feeling that brings on a new season of activities and adventures. That’s why I’ve put together my bucket list items to do this fall in Brew Town.

Chase the Fall Colors

Wisconsin is so beautiful in the fall, so I recommend spending as much time outside as possible! Hiking is a great way to enjoy the changing colors around the state, and yes, even in a city like Milwaukee.

Fall Colors

Some beautiful area hiking trails include The Milwaukee Lakefront Trail, Boerner Botanic Gardens, and Lapham Peak. These are great trails with beautiful views filled with fall colors. Want to chase the colors throughout the state? Check out the Fall Color Report from Travel Wisconsin to find where to go to get the best fall foliage!

Attend a Festival

Milwaukee is known as the city of festivals, so this wouldn’t be a Milwaukee Bucket List without a festival or two thrown into the mix! The Public Market Harvest Festival is an annual festival that takes place on October 20th right outside Milwaukee Public Market. With a handful of fall activities, there is also live cider pressing and beer tastings!

Throughout the Fall, many cities have Oktoberfest celebrations, but Milwaukee is rich in German history and a great place to celebrate the season! Milwaukee’s Oktoberfest runs from October 5th-7th, and is free for all ages. Its a great place to go to gather with family, and to enjoy some German beer and live music. If you’re looking for more Milwaukee festivals, check out

Go Apple Picking

Yes, this is a typical fall activity, but hey, it’s super fun! Going with friends or family always makes for a great afternoon. My two favorite places to go near Milwaukee are Barthel Fruit Farm and The Elegant Farmer. Both have a great selection, and amazing treats and cider for sale in addition to the apples you picked. And, let’s be honest, who doesn’t love freshly made apple cider donuts and apple pie?

Apple PickingApple Cider Donut

Tailgate with Friends

Growing up in the Chicago area, I was never really exposed to tailgating. But once I moved to Wisconsin, I got plenty of opportunities! It’s a great way to cheer on your favorite team and enjoy the fall weather. From playing cornhole, to enjoying a hard cider and grilling up some brats, nothing can get more Wisconsin than tailgating.

Head to a Brewers tailgate at Wrigley North (Miller Park) during play off season, there are plenty of bars that will shuttle you to the park if you want to meet up with friends. Or if you’re in Wisconsin on a Saturday or Sunday, be sure to check out a Badger or Packer tailgate. You will not be disappointed!

Looking for more things to do in Milwaukee? Be sure to check out Passports & Cappuccinos for all things Milwaukee, and stay tuned for my next post on Girl Meets Party!

Meet Jen

I’ve always had a love affair with creation. Since I was a child, I handmade my gifts or combined toys to design something new. Fast forward twenty years, and I’m still making my gifts every holiday and designing new ways to do things.


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In order to grow my small business, I earn revenue in a few different ways. I publish sponsored posts from time to time, which are always labeled. Sometimes I earn an affiliate commission on the sales of products or business resources I link to. I only feature items I genuinely love and want to share. Thank you for reading and supporting my small business!

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