Ultimate Fall Bucket List :: 100 Things to Do in Milwaukee this Autumn

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This year’s bucket list offers 100 ideas of things to do this fall for every budget, interest, and age. We’ve even included some fun ideas for date nights as well as for when you get together with the girls. Think you’ve done it all in Milwaukee, think again! (Please note to check each event/business website for the most up to date information.)

2019 Ultimate Milwaukee Fall Bucket List

Milwaukee Fall with the Family

  • Pack up your summer clothes and bust out the boots and scarves!
  • Join Milwaukee at the Zoo for Fall Family Free Days – October 5th, November 2nd, and December 7th. 
  • Head to Apple Harvest Fest in Waukesha on September 21st for a day full of hay rides, nature walks, and the star of the show, apples!
  • Go to Harvest Fair (September 27-29) at the Wisconsin State Fair Grounds. Admission is free and you can enjoy live entertainment and fun family activities (some require purchasing activity tickets). 
  • Run, walk, or tiptoe through a corn maze!
  • Neighborhood Night at Betty Brinn Museum offers free admission on the third Thursday of every month from 5-8pm. 
  • Rake a leaf pile…and jump right in!
  • Settle in for a night of pumpkin carving and spooky stories. 
  • Take a Sunday drive through the fall colors
  • Go trick or treating. 
  • Go apple picking
  • Go for a hay ride
  • Come out for a Milwaukee tradition at Briggs & Al’s Run & Walk to support Children’s Hospital on September 14th. 
  • Dress up for Boo at the Zoo
  • Spend the evening of October 18th at Kids Night Out with the Wisconsin Humane Society. 
  • Take a group – the family, the girls, or a double date – and go to a painting bar
  • Make your own caramel apple, take a train ride, or find your way through the corn maze at The Elegant Farmer for Autumn Harvest Festival.
  • Support our local home teams and take the family to a sporting event or a Friday night high school football game.
  • Go to a pumpkin patch
  • Decorate trick-or-treat bags with your ghouls and goblins!
  • Send notes to family and friends telling them why you’re thankful for them.
  • Make a gratitude jar and add a slip of paper each day leading up to Thanksgiving. Read them aloud before dessert!
  • “Boo” your neighbor with a random act of kindness and hope it catches on!
  • Build a blanket fort on a rainy day and take a family nap inside.
  • With three different distances for the whole family, check out the Trick or Trot Run/Walk in Greenfield on October 5th.
  • Introduce your kiddo(s) to your favorite childhood Halloween movie or special. Whether its Hocus Pocus or The Great Pumpkin Charlie Brown, chances are that they’ll love it too.
  • Get a start on Christmas shopping (and maybe make a few dollars) at the Just Between Friends of Milwaukee Fall/Winter sales event from September 14th-17th.
  • If you or your child(ren) are into cars, head on over to the Downtown West Allis Classic Car Show on October 6th.
  • Remember to “fall back” on November 3rd and curse when your kids wake up anyway.
  • Take your family photos outdoors. In need of a photographer? Check out some of our favorites on our home page!
  • Have some Fall Fun on the Farms at Old World Wisconsin on weekends from September 7th through October 13th.
  • Take the family down to the Oak Creek Fall Festival on October 19th. It’s an indoor-outdoor event that celebrates “everything autumn.”
  • Fun for everyone, learn something new at the Maker Faire, a venue for these “makers” to show hobbies, experiments, projects.
  • Run, walk, or tiptoe through a corn maze!
  • Neighborhood Night at Betty Brinn Museum offers free admission on the third Thursday of every month from 5-8pm. 
  • Rake a leaf pile…and jump right in!
  • Go trick or treating. 
  • Go apple picking
  • Go for a hay ride
  • Cut open an apple and use it as a stamp to make apple art!
  • Grab your little artist(s) and make a handprint turkey.
  • Build a blanket fort on a rainy day and take a family nap inside.
  • Check out a fall-themed book at your local library or at a local free little library!
  • Remember to “fall back” on November 3rd and curse when your kids wake up anyway.
  • Have some Fall Fun on the Farms at Old World Wisconsin on weekends from September 7th through October 13th.
  • Collect leaves and help your toddlers turn them into works of art.
  • Get one last trip in at your favorite playground…or check out a new one!
  • Enchanted Tales Film Series at Marcus Majestic: (Disney’s Enchanted Tales Film Series – September 6-29: At select locations, moviegoers can relive the magic of “Moana,” “Cinderella,” “Peter Pan” and “The Little Mermaid” on Fridays, Saturdays and Sundays for just $6.)
  • Settle in for a night of pumpkin carving and spooky stories. 
  • Put on your brave face and visit a haunted house.
  • Bike the Glacial Drumlin Trail
  • Go to Fright Fest at Six Flags which runs from September 14th to November 4th. 
  • Take a group – the family, the girls, or a double date – and go to a painting bar
  • Expect trills, chills, and frightful fun at Halloween Spooktacular at MKE Zoo on October 25th and 26th. 
  • Bring your big kids along to Doors Open MKE and chat about the history, architecture and artistry in our city. 
  • Support our local home teams and take the family to a sporting event or a Friday night high school football game.
  • “Boo” your neighbor with a random act of kindness and hope it catches on!
  • Introduce your kiddo(s) to your favorite childhood Halloween movie or special. Whether it’s Hocus Pocus or The Great Pumpkin Charlie Brown, chances are that they’ll love it too.
  • Have some Fall Fun on the Farms at Old World Wisconsin on weekends from September 7th through October 13th.
  • Escape video games and explore the great outdoors on a hike with some friends!
  • Visit Holy Hill
  • Take a Sunday drive through the fall colors
  • Take a hike at one of the many area hiking trails and do a nature scavenger hunt. 
  • Bike the Glacial Drumlin Trail
  • Sit back and relax at a backyard bonfire. 
  • Plant some autumn flowers.
  • Go puddle jumping – rain, mud or both!
  • Collect leaves and help your toddlers turn them into works of art.
  • Watch critters of all shapes and sizes take to the streets for the annual Brady Street Pet Parade and Pet Blessing on October 13th.
Milwaukee bucket list for homebodies
  • Make a Halloween costume! 
  • Bake an apple pie. 
  • Sit back and relax at a backyard bonfire. 
  • Paint a teal pumpkin to make your house allergy friendly for trick or treaters. Check out these non-candy ideas to hand out!
  • Have a contest to see who can make the best tasting s’mores – via bonfire or candlelight!
  • Curl up on the couch on a chilly day with a homemade Hot Toddy. 
  • Start looking into indoor activities (as it is Wisconsin after all).
  • Send notes to family and friends telling them why you’re thankful for them.
  • Knit a fall scarf with needles or try your hand at finger knitting.
  • Check out fall-themed wreaths on Pinterest and give your favorite a try!
  • Break out your favorite cozy sweater. Don’t have one? Check out your favorite thrift store and find a new favorite.
food + Drink Milwaukee bucket list
  • Take a tour of Lakefront Brewery for half the regular price every Monday from 4-8pm and also enjoy half price tap beer and cheese curds.
  • Bake an apple pie. 
  • Drink a seasonal brew
  • Have a contest to see who can make the best tasting s’mores – via bonfire or candlelight!
  • Make some fall sangria and invite the girls over for a craft night so you can help each other out.
  • Keep the pumpkin seeds when carving and toast them for a healthy snack.
  • Make popcorn from a cob.
  • Make a fun pumpkin-shaped treat. The options are endless! We’re thinking of pancakes, Rice Krispie treats, pizza or quesadillas.
  • Make your own harvest trail mix using popcorn, pretzels, peanuts and fall favorites like candy corn (if that’s your thing).
  • Make an extra loaf or pie for your child’s teacher to thank them for a great school year (so far).
  • Have caramel apple sundaes one night for dessert.
  • Find a tried and true pumpkin bread recipe and have a baking day!
  • Eat an apple cider doughnut while sipping apple cider (hot or cold, your choice).
  • Enjoy your favorite warm breakfast. We recommend this Colectivo Copycat Baked Oatmeal! YUM!
  • Break out your favorite stew or soup recipe. Looking for something new? Try this one!
  • Fill your belly at Chili’n on the Ave on October 12th in East Tosa.
  • September is the beginning of Packer season! What a perfect time to put up fall decor and host a Packer party! More into college ball? Jump Around with Bucky
  • Remember that it’s hockey season too and check out the Milwaukee Admirals Season Opener at the US Cellular Arena on October 12th.
  •  Head on over to the Great Pumpkin Run at Swan’s Pumpkin Farm on September 28th. You can do the 5K holding a pumpkin (if you want)!
Milwaukee Bucket list date night
  • Settle in for a night of pumpkin carving and spooky stories. 
  • Put on your brave face and visit a haunted house.
  • Take a Sunday drive through the fall colors
  • Get a babysitter for the littles and have a date night at the Cedarburg Wine and Harvest Festival, September 21-22; because Mom and Dad need a fall celebration too. 
  • Go to Fright Fest at Six Flags which runs from September 14th to November 4th. 
  • Take a tour of Lakefront Brewery for half the regular price every Monday from 4-8pm and also enjoy half price tap beer and cheese curds.
    Take a group – the family, the girls, or a double date – and go to a painting bar
  • If you or your child(ren) are into cars, head on over to the Downtown West Allis Classic Car Show on October 6th.
  • The China Lights at the Boerner Botanical Gardens are back and would make a great date night anytime from September 13th to October 20th!
  • Make Bay View Gallery Night on September 27th your next date night.
  • Grab your hunny and learn something new at the Maker Faire, a venue for these “makers” to show hobbies, experiments, projects.
  • Perhaps one of the most beautiful places in the area, Pieper’s Porch Winery and Vineyard is the perfect spot to toast your love with a glass of wine.
Milwaukee Bucket List = Festivals + Music
  • Head to Apple Harvest Fest in Waukesha on September 21st for a day full of hay rides, nature walks, and the star of the show, apples!
  • Go to Harvest Fair (September 27-29) at the Wisconsin State Fair Grounds. Admission is free and you can enjoy live entertainment and fun family activities (some require purchasing activity tickets). 
  • Go to New Berlin’s Apple Fest on October 6th and tour the historical museum, ride the barrel train, and square dance in the barn. 
  • Watch the Milwaukee River Challenge on September 21st. 
  • Chill out at the 51st Annual Cheery Cherry Fall Fair in Menomonee Falls on September 22nd.
  • Check out the Maker Faire Milwaukee at the State Fair Grounds, September 14-15th. 
  • Get a babysitter for the littles and have a date night at the Cedarburg Wine and Harvest Festival, September 21-22; because Mom and Dad need a fall celebration too. 
  • Go out with the girls to Milwaukee Oktoberfest held October 4th to 6th.
  • Take Fido (or Frida) to the 7th annual Barktoberfest and enjoy a Stein on September 14th. 
  • Get down and dirty at the Tomato Romp on September 7th. 
  • Join Historical Downtown Delafield for the Fall Art Walk on September 13th. 
  • Head down to Downtown Historic Cedarburg for a perfect October (the 5th and 6th) weekend at Oktoberfest.
  • See what’s new in the film world with the Milwaukee Film Festival happening October 17th through October 31st.
  • Check out Bay View Bash on September 21st– with or without the kids!
  • If you’re a fan of Chill on the Hill, check out First Man at Film on the Hill on September 28th.
  • Check out dance, drum and singing competitions honoring Native Americans at the Hunting Moon Pow Wow held October 18-20 at the Wisconsin Center.
  • Make sure you subscribe to the MKE Mom’s Blog Newsletter so you don’t miss out on any of our upcoming fun!

It’s time for FALL – the season of pumpkin spice lattes, cute boots, giant leaf piles and so much more! There are so many things to do in Milwaukee this fall, and we can hardly WAIT to get started! We are famous for our festivals, fairs and fun so be sure to get out there and see what the Milwaukee area has to offer. 

For more great resources for fall in Milwaukee, be sure to check out our many guides to the best of autumn in the area: 

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