Fall is just around the corner, and you are still unsure of how to spend the season? Well, if you are from Milwaukee, Wisconsin, this is the page for you.
On this site you will find the top 3 activites to engage in to elevate your fall experience. From pumpkin bowling to apple picking, there are a wide range of familiy friendly events based on your preferences. All of these locations are near the city of Milwaukee, so there won't be a need to travel far to enjoy the season.
Here is a list of the events being covered:
If you are interested in any of the following, links will be provided with further information such as dates and prices.
Harest Fair is a large event hosted on the State Fair grounds in West Allis. If you are familiar with State Fair, it is a very similar experience. If you aren't, don't worry, because all you need to know will be right here.
What will probably catch your eye initially is the concession stands. Spread across the entire park are various food vendors that offer any kind of meal/snack you are looking for. There are also specialized stands where you can find caramel apple or pumpkin themed foods. Though, the food is hardly the most interesting part of this festival despite how great it might taste. It is extremely kid friendly, so bring your family to get involved in activities like pumpkin bowling, scarecrow stuffing, haybale rides, and more! Everything provided is also topped off with live music performances by various bands everywhere you go. This is highly recommended for people who don't have a lot of time to spend during the autumn months as it covers so many activites in just one place. However, make sure you check out the website and mark your calendars as it only lasts one weekend! (typically in October).
As of 2026,
The dates and times for Harvest Fair are:Friday, October 2: 5pm – 11pm
Saturday, October 3: 10am – 11pm
Sunday, October 4: 10am – 6pm
If this is something that might interest you, check out the link here.
Apple Holler is a family owned farm located in Sturtevant, Wisconsin. Similar to Harvest Fair, this is definitely a place you will want to take your kids. While it is most known for it's apple orchard, it offers so much more than just apple picking.
Apple picking is one of the staple activites to do during fall and this is just the perfect place. If the name wasn't obvious, this farm offers a pick-your-own fruit (commonly apples) for anyone to collect and enjoy. Alongside that, there is a selection of baked goods such as apple cider donuts that are absolutely amazing, and also a rustic-themed restaurant with delicious meals. You may be thinking, why would I drive my kids all the way here just to pick some apples and grab a snack? Well, Apple Holler also provides tractor-drawn train rides, hayrides, a corn maze, and cute barn animals to look at and pet! This location is open year-round for anyone interested, but it is best to go from late August through October during prime fall time.
To learn more about Apple Holler, click the link here.
There are plenty of options near Milwaukee for a simple farmer's market, but South Shore arguably offers the best, selling farm fresh and local food along the shores of Lake Michigan. Hosting a variety of shops and food stands, the view is remarkable during the fall, perfectly capturing autumn vibes.
Typically, most people find their way to farmer's markets with the goal of purchasing fresh goods. While this can absolutely be accomplished at South Shore with over 50 regional vendors, it is so much more than that. With such a friendly community, you are bound to make connections within a beautiful environment. There is also live musical performances weekly, to fill the air with melodious sounds. Throughout the plaza, you will also find nonprofit organizations who do so much for the community, so you can also use it as an opportunity to learn more. South Shore Farmer's Market is open from June to October, but during the fall it is an absolute delight, and spending your time here on a cool autumn afternoon would be perfect if you are looking for a more calm, relaxed day.
If you seek out a shopping trip like this, check out their site here.
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If you have any questions about what more to do during the fall season, reach out at autumn@fall.com.