8 Milwaukee Date Ideas to Try This Fall

Whether it’s your first date or your hundredth, these dates will make for a day to remember.


A Picnic with a View

Make it simple by packing sandwiches and an outdoor blanket or try out a local luxury picnic service like the Pack Picnic Company, Perfect Picnic MKE or Picnic MKE. Consider heading over to Lake Park to enjoy the colors of the changing trees or wandering down to the Bradford Beach to take in the bright blue lake before it turns icy cold.

Photo by Visit Milwaukee


The Classic Pumpkin Patch

Nothing screams fall more than throwing on some boots, hopping on a hayride and ending up in the middle of nowhere surrounded by the infamous orange squashes that we love so dearly during this season. This beloved fall activity is a wonderful date idea because you’ll get to spend time in nature, enjoy conversation on the inevitable hayride and you get to schedule another date to carve the pumpkins you pick out. Here’s our 2021 Fall Pumpkin Patch Guide to help you get started planning this one.

Photo by Getty Images



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A Cooking Class for Two

If you’re a foodie, this one’s for you. Catch a cooking class at Glorioso’s or Milwaukee Public Market to learn how to make a delicious meal! Some of the upcoming classes at Gloriosos’s include “Making Fresh Pasta: Carbonara,” “Cooking the Classics: Pork Tenderloin Rollatini,” “Butternut Squash Risotto with Maple Polenta Cake” and more. At Milwaukee Public Market, upcoming classes include “It’s Getting Chili” and “Coffee Toffee and Hot Cinnamon Peanut Brittle.”

Students learn to make fresh gnocchi at Glorioso’s Appetito cooking school. Photos by Aliza Baran.


An Apple Picking Adventure

Walking around an apple orchard is a wonderful place to get to know someone. The secluded orchards offer an opportunity to walk and talk, and to occasionally enjoy a bite of a fresh apple or two as you pick them off the trees. Not to mention, the cute baskets they give you and the bright red and green apples hanging all around are sure to make for a cute picture to remember this small adventure. Here are some apple orchards near the Milwaukee area.



If apple or pumpkin picking isn’t really for you, consider taking your date on a hike! We even rounded up eight hidden suburban hikes that would make great date destinations.

Seven Bridges Trail; Photo by Isabel Ditchev


A Trip to the Farmers’ Market

Head over to a local farmers’ market this fall to pick up some veggies, bread, food and  maybe even a bouquet of flowers (wink, wink!) with your person. Afterwards, you could even try cooking something together with the food you pick up. Be sure to go soon because many farmers markets end in late October or early November.

Photo courtesy of West Allis Farmers Market


Chill at a Beer Garden

Grab a beer and some good food at a local beer garden this fall before the weather cools off. This is a relaxing, chill date that is sure to bring great conversation and lots of fun. Here are some beer gardens that are still open for the season (but are closing soon!). Weather too cold? Try checking out one of these local breweries instead.

Hubbard Beer Garden; Photo by Visit Milwaukee


Catch a Movie at a Local Theater

Grabbing a movie may just be the most classic date in the history of dates, so why not put a local spin on it and catch a movie at a local theater. The Oriental Theater just reopened in August, or the Landmark’s Downer Theater is another option.

Oriental Theater
Photo by Pamela Strohl for Milwaukee Film



Brianna Schubert is the associate digital editor and writes about art, culture and more at Milwaukee Magazine. When she’s not writing/editing, she’s likely reading (follow her book reviews on Instagram at @read_with_bee), cooking or listening to Taylor Swift.