2020 Milwaukee Fall Bucket List: Fun 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. 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.)

The team at Milwaukee Mom is working hard to remain your go-to spot for parenting resources in the Greater Milwaukee Area. While we will do our best to be as up-to-date as possible, please be aware that we are still dealing with changes related to the COVID-19 Pandemic. Please consult your local public health authority for social distancing recommendations and call ahead to confirm hours and offerings of any business or organization listed.

2020 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 3rd, November 7th, and December 5th.
  • Head to Apple Harvest Fest in Waukesha for a day full of hayrides, nature walks, and the star of the show, apples! 2020 event canceled.
  • Go to Harvest Fair at the Wisconsin State Fair Grounds. Admission is free, and you can enjoy live entertainment and fun family activities (some require purchasing activity tickets). 2020 event canceled.
  • 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 5-8 pm. The museum is currently closed due to Covid-19. Please check the website for updates.
  • 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. Get creative and build a Candy Chute to hand out candy from a safe distance!
  • Go apple picking.
  • Go for a hayride! 
  • Join Briggs & Al’s Run & Walk Virtual Family Fun to support Children’s Hospital held on August 1- September 12th.
  • Dress up for Boo at the Zoo held on October 16th & 17th.
  • Spend an evening 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. Currently holding virtual painting sessions.
  • 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.
  • 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.
  • Set up a Virtual Game Night on the HouseParty app!
  • 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 3rd.
  • 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.
  • If you or your child(ren) are into cars, head on over to the Downtown West Allis Classic Car Show on October 4th.
  • Remember to “fall back” on November 1st and curse when your kids wake up anyway.
  • Take your family photos outdoors. Check out our Guide to Local Photographers on our home page!
  • Have some Fall Fun on the Farms at Old World Wisconsin on weekends. 2020 event canceled. 
  • Take the family down to the Oak Creek Fall Festival on October 24th. 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!
  • Visit the Dinosaur Adventure Drive-Thru with about 100 life-sized dinosaurs!
  • Neighborhood Night at Betty Brinn Museum offers free admission on the third Thursday of every month from 5-8 pm. The museum is currently closed due to Covid-19. Please check the website for updates.
  • Rake a leaf pile…and jump right in!
  • Go trick or treating.
  • Go apple picking.
  • Go for a hayride.
  • 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 a local free little library!
  • Have some Fall Fun on the Farms at Old World Wisconsin on weekends. We are waiting on an update on the 2020 event.
  • 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!
  • Watch a Family-Friendly Film Series at Marcus Majestic. No current Family-Friendly Film Series at the moment.
  • Book a private theater at Silverspot Cinema for a Family Movie Night on the Big Screen! With plenty of room to spread out, you can invite a larger group and enjoy content from your own streaming service in a real theater!
  • 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. Due to Covid-19, you must make a reservation and purchase a park permit before visiting the trail. 
  • Go to Fright Fest at Six Flags. Theme Park is currently closed.
  • Expect thrills, chills, and frightful fun at Halloween Spooktacular at MKE Zoo. 2020 event canceled.
  • Bring your big kids along to Doors Open MKE and chat about the history, architecture, and artistry in our city vie Virtual from Sept 26th-October 11th.
  • “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. Waiting on an update on the 2020 event.
  • Escape video games and explore the great outdoors on a hike!
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.
  • 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. (2020 version involves Zoom, of course)
  • 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. Are you looking for something new? Try this one!
  • Fill your belly at Chili’n on the Ave in East Tosa. 2020 event canceled.
  • September is the beginning of Packer season! What a perfect time to put up fall decor and wear your green and gold! 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.No games are scheduled yet. Check the website for updates.
  • Head on over to the Great Pumpkin Run at Swan’s Pumpkin Farm. You can do the 5K holding a pumpkin (if you want)! 2020 run event will be held virtually.
  • Try a new workout class! Not sure where to start? Check out the Milwaukee Area Fitness Guide.
  • Bike the Glacial Drumlin Trail. Due to Covid-19, you must make a reservation and purchase a park permit before visiting the trail. 
  • September is the beginning of Packer season! What a perfect time to put up fall decor and wear your green and gold! 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. No games are scheduled yet. Check the website for updates.
  •  Head on over to the Great Pumpkin Run at Swan’s Pumpkin Farm. You can do the 5K holding a pumpkin (if you want)! Run will be held virtual this year. 
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 because Mom and Dad need a fall celebration too. 2020 event canceled.
  • Go to Fright Fest at Six Flags. The theme park is currently closed.
  • Take a tour of Lakefront Brewery.
  • If you or your child(ren) are into cars, head on over to the Downtown West Allis Classic Car Show. 2020 event canceled.
  • The China Lights at the Boerner Botanical Gardens are back and would make a great date night. 2020 event canceled.
  • Attend Bay View Gallery Night for your next date night. 2020 event canceled.
  • Grab your Hunny and learn something new at the Maker Faire, a venue for these “makers” to show hobbies, experiments, projects. 2020 event canceled.
  • 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 for a day full of hayrides, nature walks, and the star of the show, apples! 2020 event canceled.
  • Go to Harvest Fair at the Wisconsin State Fair Grounds. Admission is free, and you can enjoy live entertainment and fun family activities (some require purchasing activity tickets). 2020 event canceled.
  • Go to New Berlin’s Apple Fest and tour the historical museum, ride the barrel train, and square dance in the barn. 2020 event canceled.
  • Watch the Milwaukee River Challenge. 2020 event canceled.
  • Chill out at the 51st Annual Cheery Cherry Fall Fair in Menomonee Falls. 2020 event canceled.
  • Check out the Maker Faire Milwaukee at the State Fair Grounds. 2020 event canceled.
  • Get a babysitter for the littles and have a date night at the Cedarburg Wine and Harvest Festival because Mom and Dad need a fall celebration. 2020 event canceled.
  • Go out with the girls to Milwaukee Oktoberfest. 2020 event canceled.
  • Take Fido (or Frida) to the 7th annual Barktoberfest and enjoy a Stein on September 19th-October 4th. 2020 event will be held virtually this year.
  • Get down and dirty at the Tomato Romp. 2020 event canceled.
  • Join Historical Downtown Delafield for the Fall Art Walk on September 11th.
  • Head down to Downtown Historic Cedarburg for a perfect October weekend at Oktoberfest. 2020 event canceled.
  • See what’s new in the film world with the Milwaukee Film Festival happening October 15th through October 29th.
  • Check out Bay View Bash on September 19th– with or without the kids!
  • If you’re a fan of Chill on the Hill, check out First Man at Film on the Hill in September. 2020 event canceled.
  • Check out dance, drum, and singing competitions honoring Native Americans at the Hunting Moon Pow Wow held in October at the Wisconsin Center. 2020 event canceled.
  • Make sure you subscribe to our Newsletter, so you don’t miss out on our upcoming fun!

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