Updated September 4, 2025
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Fall in Milwaukee is packed with festivals that celebrate everything we love about the season – crisp apples, bright pumpkins, live music, cultural traditions, and plenty of family fun. From September through October, you’ll find events happening across the city and surrounding communities that bring people together to enjoy Wisconsin’s best autumn traditions.
Over the years, my kids and I – along with the MKE With Kids team – have attended many of these festivals ourselves, and we’ve listened to our readers’ recommendations, too. This roundup highlights the most family-friendly Milwaukee fall festivals happening in 2025, so you can plan ahead and make the most of this short but magical season.
For even more seasonal fun, check out our interactive Milwaukee Fall Fun Map with pumpkin patches, corn mazes, and local favorites! And since apple picking is just the beginning of fall fun in Wisconsin, don’t miss our complete Fall Family Fun Guide for Milwaukee for hayrides, festivals, and more family adventures.
Here’s your guide to the best fall festivals around Milwaukee for families in 2025.
Best Fall Festivals Around Milwaukee
1. Harvest Fair (State Fair Park)
Sept. 26 – 28, 2025
Wisconsin State Fair Park, 640 S. 84th St., West Allis, WI 53214
wistatefair.com
New this year: Brand new Cream Puff flavors include Pumpkin Spice & Apple Crisp! Plus, Culver’s Curdtoberfest will offer free samples, kid-friendly activities, and live entertainment in a Bavarian-inspired Root Beer Garden.
Enjoy free live entertainment on several stages, including local artists, Amphitheater headliners, lumberjack shows, pumping bowling, make-your-own scarecrow, a Farmer’s Market, and food galore!
Looking for pumpkins beyond the fairgrounds? Explore our roundup of the best pumpkin patches near Milwaukee for more places to pick the perfect one.
2. Apple & Sunflower Fest (Basse’s Taste of Country)
Aug. 30 – Sept 1st, Sept. 5th – 7th, & Sept. 12th – 14th, 2025 Only (weather permitting)
3190 County Line Q, Colgate, WI 53017
bassesfarms.com
Walk or ride the Grain Train out to the fields, where you can enjoy picking your own apples from the orchard (Honeycrisp and several other varieties are available), and spend some time wandering through the beautiful zinnias and 5-acre sunflower maze. Don’t forget to have your camera ready for many breathtaking photo ops!
👉 Love wandering through flowers? Don’t miss our guide to the best sunflower mazes near Milwaukee for more picture-perfect family adventures.
3. Cider Sunday at Wehr Nature Center
Sunday, October 5, 2025
Celebrate fall during this family-friendly event for all ages.
- This year expect to:
- Listen to the sounds of live music from The Bluegrass Allstars and The Sweet Sheiks
- Amble the trails among the autumn colors, enjoy a new apple-themed Story Stroll and sensory scavenger hunt
- Participate in an interactive presentation with live animals by David Stokes
- Enjoy tasty apple treats and handmade apple cider, as well as homemade cider beer provided by the Milwaukee Beer Barons
- Engage in pumpkin bowling, children’s crafts, activities, and more!
👉 Make the most of those golden leaves with one of the best fall hikes near Milwaukee — the perfect way to enjoy peak color season.
4. Autumn Harvest Fest at The Elegant Farmer
Sept. 7 – Oct. 27, 2025 (Saturdays and Sundays only)
1545 Main St., Mukwonago, WI 53149
Admission: FREE (fees apply for activities, apples and pumpkins)
elegantfarmer.com
Whether you’re continuing a family tradition or starting a new one this fall, The Elegant Farmer offers an old-fashioned, on-farm experience.
This fun family event features apple picking (find current varieties on their website and Facebook page), corn maze, laser tag, pumpkin patch, tractor-pulled hayrides, pony rides, the Smilin’ Barn Café and more.
Pro Tip: The East Troy Railroad also stops here, so you can make a train ride part of your day as well. Open Saturdays and Sundays only; admission and parking are free.
Pro Tip: The early birds get the apples! To avoid the crowds, arrive earlier in the morning or after 3 p.m. You can grab coffee and donuts in the market when it opens at 9 a.m., then cross the street to the orchard when it opens at 10 a.m.
👉 Since Elegant Farmer is also known for its orchards, check out the best apple picking spots near Milwaukee to plan another fun family outing.
5. Friends of Retzer Nature Center’s Apple Harvest Festival
Saturday, Sept. 20, 2025
Retzer Nature Center, S14 W28167 Madison Street, Waukesha
waukeshacounty.gov
Come enjoy the Apple Market with sweet treats and cider. Fun children’s activities include a Passport Expedition on the accessible Discovery Trail, a self-guided story hike, a scavenger hunt on Scarecrow Lane, and planetarium shows.
Parents will love shopping arts and crafts vendors, bidding at the silent auction, relaxing at the beer garden (try the Retzer Apple Ale) and listening to live music by JC Ayer.
👉 Retzer is famous for its fall colors, but there are many more places to see them. Check out our guide to the best fall foliage views near Milwaukee.
6. Wine & Harvest Festival in Cedarburg
Sept. 20 – 21, 2025
N70 W6340 Bridge Road, Cedarburg, Wisconsin 53012
Kick off this beautiful season with a sweet and savory weekend at the 50th Annual Wine & Harvest Festival in historic downtown Cedarburg.
There will be live music, grape stomping, pumpkin weigh-ins, a hilarious giant pumpkin regatta (Sunday, 2 p.m.), a classic car show, a Kids Korner with petting zoo, bouncers and barrel train, wine tasting and more!
👉 Kids will love the barrel train and petting zoo here — and you can find even more family-friendly farms in our list of the best petting zoos near Milwaukee.
7. The Hollow at Phantom Lake
Weekends in October
S110W30240 YMCA Camp Road, Mukwonago, WI 53149
Website
Take a stroll and enter a world of enchantment, filled with 3000 hand-carved illuminated jack-o’-lanterns. This outdoor, family-friendly evening under the stars is sure to become a yearly tradition.
👉 If your kids love not-so-spooky fun, don’t miss our complete guide to Halloween family fun in Milwaukee.
8. Annual Harvest Festival at Milwaukee Public Market
Date TBD
This annual festival is a celebration of the public market’s anniversary. It is a free event that is fun for the whole family with food, music, and autumn inspired activities. Taste hand cranked apple cider, build your own scarecrow, go pumpkin bowling, get your face painted, and more.
Attendees 21 years of age or older can take part in a fan-favorite tradition of sampling Lakefront Brewery Pumpkin Lager tapped from the market’s giant pumpkin.
The festival is located at the Riverwalk Commons space, located across the street from the Milwaukee Public Market along the river.
9. Fall Fest at Basse’s Taste of Country
September 20 – October 31, 2025
190 County Line Q, Colgate, WI 53017
bassesfarms.com
Start your family traditions and come explore Happy Jack’s Pumpkin Land at Basse’s for the ever-improving Pumpkin Festival just 25 minutes northwest of Milwaukee.
Pick your own perfect pumpkin from the patch, challenge yourself in the 8-acre corn maze, and enjoy 65+ fun activities for the whole family, including jumping pillows, train, ropes course, duck races, arcade games and so much more! They add new activities every year.
There’s also pig races, dog shows, lumberjack shows, cowboy stunts, a dance party, and a candy cannon. Purchase corn stalks, straw bales, pumpkins of all sizes, squash, gourds, and more from the market.
👉 Want more ways to get lost in the season? Explore our guides to the best corn mazes near Milwaukee and the best hayrides around Milwaukee.
10. Sturgeon Fest
Sunday, Sept. 28, 2025
Okay, okay, this isn’t quite a “Harvest Festival”. But Sturgeon Fest happens every year in the Fall, and it’s definitely worth your time! It’s hosted by Riveredge Nature Center and held in Milwaukee’s beautiful Harbor District.
Sturgeon are the oldest and largest species of fish in the Great Lakes. But in less than 200 years, human influence caused the sturgeon population in Lake Michigan to plummet.
At this festival, you can sponsor a young sturgeon and hand release them into Lake Michigan. Plus, there’s live music and plenty of activities for the whole family.
More Fall Festivals:
Mukwonago Fall Fest
Saturday, Sept. 20, 2025, 10 a.m.-4 p.m.
Downtown Mukwonago
Admission: FREE
Located in the heart of downtown Mukwonago, this family-friendly annual event features local craft and food vendors, a chili cook-off, live music, pumpkin decorating, bounce houses, family photo opportunities, and a DJ.
Piala’s Fall Festival
Sept. 27 & 28, 2025
Piala’s Nursery & Garden Shop, S39W27833 Genesee Rd, Waukesha, WI 53189
Admission: FREE
This fun-filled, family-friendly weekend at the nursery features a craft fair, live music, fresh food, festival-only sales and plant specials, and Piala’s peacock palace. For the kids, there’s a bounce house, a giant slide, games, and a fire department meet and greet – all for free! Enter to win an amazing door prize by donating a non-perishable or household item to the Food Pantry.
Greenfield Fall Family Fest
Saturday, October 4, 2025
Konkel Park, 5151 W. Layton Ave., Greenfield, WI 53220
Admission: FREE
This free event is held in conjunction with the Annual Trick-or-Trot Run/Walk. Enjoy fall-themed family activities, including inflatables, a petting zoo, pumpkin bowling, face painting, a haystack play area, animal balloons, bingo, games and more.
Enter the costume contest (youth and adult prizes available), or try your hand at the pumpkin pie eating contest! Food trucks, beverages, and beers will be on hand as well.
Great Pumpkin Festival
Oct. 22 – 25, 2025
Old School House Park, 5240 N. Marlborough Dr., Whitefish Bay, WI 53217
Admission: FREE
A full festival will take place Wednesday through Saturday, featuring live music along with food vendors and a beer tent. Residents will be able to pick up pumpkins at various times throughout the week and then return them to the park to be part of the walk-through lighted display on Sunday and Monday night (6-9 p.m.). There will be no pumpkin carving done on site, and no festival activities will take place on Sunday and Monday.
Thiensville Applefest
Sunday, Oct. 5
Details TBD
🍺 Don’t forget: Milwaukee is also home to some of the Midwest’s best Oktoberfest celebrations, complete with music, dancing, and German-inspired food. If your family wants to join the festivities, check out our complete guide to Family-Friendly Oktoberfest Events in Milwaukee.
Calie Herbst, Editor-in-Chief of Milwaukee With Kids, has spent over a decade combining her experiences as a parent of three to create a hub for Milwaukee’s family adventures.
Her decade-long teaching career in Milwaukee Public Schools and academic background, including a Master’s in Teaching from Marquette University and dual B.A.s in Sociology and Spanish from the University of Wisconsin – Madison, fuel her passion for inclusive and engaging family content.
Calie is also a recognized voice in local media, contributing to WISN Channel 12 News, WTMJ Wisconsin Morning News, Fox 6’s Real Milwaukee, and B93.3.
Discover more about Calie’s journey and editorial approach on her About Page and Editorial Policy Page.
