top of page

Fun Fall Activities Around Madison This October!

With cold weather comes fall-themed activities! Temperatures dropping below 70 degrees make us crave pumpkin spices, apples, candy, and costumes! Check out some of the fun fall events and activities around the Madison area this year. Hopefully, these events will help with the seasonal cravings and enjoy the brisk air and changing colors.

Halloween at Cave of the Mounds - All October

Don’t be afraid of the dark! Experience the Cave of the Mounds in October for HOLLOW-een in the cave! Anyone who wants to join can for an extra $2 charge per person when buying a ticket. This includes a reusable cloth bag, and crystals/fossils that you will get in a trick-or-treat style throughout the cave! Purchase at the Ticket Desk!

2975 Cave of the Mounds Road, Blue Mounds

Backlight Tours at Cave of the Mounds - October 2, 7, 16, 21, and November 6, 11, 20, 25, and December 4, 9, 18 - 4:30 PM

Unique Experience to explore the Cave of the Mounds by Black Light. Watch the cave glow under UV Light. You will learn about ultraviolet light, fluorescence, and see the speleothems GLOW! The tour price includes a black light rental and a guided tour of Cave of the Mounds. Purchase tickets online ahead of time or at the Ticket Desk!

2975 Cave of the Mounds Road, Blue Mounds

Fall Orchard Tours at the Cider Farm - Sunday, October 2, 2 pm & 3 pm

Tour The Cider Farm orchard to see the unusual apple varieties used to make ciders and apple brandy! Learn how they manage them organically and enhance the natural environment of the 166-acre farm near Mineral Point in Wisconsin’s Driftless region. You’ll have the opportunity to taste three different ciders made from the orchard’s apples including the limited-release, Dabinett Cider. The tour will be just over one hour; afterward, guests are welcome to walk around the orchard, woodlands, and prairie. Depending on the time of the harvest you may be able to see the apple press in operation.

You can make it a picnic! Bring a picnic blanket or chairs and advance order a boxed cheese board and cider for you to enjoy on-site. Be sure to select the Cheese & Cider add-on when purchasing your tickets.

The Cider Farm Orchard, 7258 Kelly Rd, Mineral Point

Drive-In Movie: Hotel Transylvania - Friday, October 7, 6:15 pm

Get ready for Halloween with a family classic, Hotel Transylvania! Watch the movie from your vehicle or bring a lawn chair or blanket to watch on the lawn of Angell Park.

Enjoy the experience of an outdoor drive-in movie to kick off October!

Angell Park Speedway, 315 Park St., Sun Prairie

The entrance to the movie is located on County Highway N.

Cambridge Farm to School Fall Fest - Saturday, October 8th, 11 am - 7 pm

This Cambridge Farm to School fundraiser includes a 5K run, chili cook-off, Art Tent, face painting, pumpkin painting, FFA animals, food, drinks, beer garden and live music featuring Little Earthquakes, Comingle, and The Lately. Enjoy the fun, music and food in support of Cambridge Farm to School programs.

West Side Park Cambridge, 300 W Water St, Cambridge

Oak Bank's Great Pumpkin Giveaway - Saturday, October 8, 9 AM - 12 PM

Oak Bank will be hosting their Great Pumpkin Giveaway. Families are welcome to join Oak Bank on their green space to pick out pumpkins, grab a goodie bag and, enjoy tractor-drawn wagon rides and a bounce house! Kids will have the opportunity to meet local mascots at the giveaway as well. All cash donations collected during the event will be donated to Wisconsin Youth Symphony Orchestras.

5951 McKee Road, Fitchburg

Pumpkin Cuck - Saturday, October 8, 3 -7 PM

Join Wisconsin Brewing Company for an evening of Fall family fun! Pumpkin Chucking, Pumpkin Carving, Special Release Beers, Live Music, Food, Vendors. There's fun for everyone at the 5th Annual Pumpkin Chuck!

Chuck pumpkins from the 15' tall trebuchet and launch them right into the pond! This event is FREE and open to the public. Kids and dogs are welcome. Sip a brew and enjoy a roaring bonfire. Don't forget to head over to the pumpkin carving station!

Activities: Pumpkin Chucking, Pumpkin Carving

Food: Mount Horeb-Barneveld Gridiron Club, Sugar River Country Bakery

Vendors: The Cursing Hippies Tie Dye

Live Music by: The Jimmys

1079 American Way, Verona

Sun Prairie Fall Fun Event - Saturday, October 15, 11 AM – 5 PM

Downtown Sun Prairie’s Cannery Square will be the place to enjoy the sights and sounds of fall! Enjoy live music performances from David Landau, Nine Thirty Standard, Jourdan Hines feat. Miss Mary, and Ryan Martin Magic in Cannery Square and on Main Street all day long!

Entertainment Schedule

  • 11 AM - 1 PM AM Ed Ford in Cannery Square

  • 1 - 3 PM Simple Company Acoustic at the Sun Prairie Historical Museum Lawn

  • 2 - 3 PM Danielle Lee with Hoop Elation LLC (live hula hoop show and demos) in Cannery Square

  • 3 - 5 PM Back2Back Acoustic in Cannery Square

  • 3:30 - 4:30 PM Halloween Sing-A-Long with Two Birds at the Sun Prairie Historical Museum Lawn

Check out the Scarecrows from the Scarecrow Contest that will be on display throughout Downtown Sun Prairie!

Looking for more pumpkin fun? Check out various games and the Giant Pumpkin, and enter the Downtown Giant Pumpkin Contest for your chance to win gift cards from Downtown Sun Prairie businesses. There will be a 1st, 2nd, and 3rd place prize for guesses that are closest to the weight of the Big Pumpkin.

Monona Fall Fest - Saturday, October 15, 10 AM Start time

Monona Fall Fest has so many things to offer! Enjoy the Hoot Hoot Hustle which is a 8K/5K/2K run/walk benefits the Winnequah School PTO and Monona Parks and Recreation. Or join the Outdoor Pie Baking & Tasting Competition from 10:00 - 11:00 am - pie viewing with pie samples from 11:00 am - 2:00 pm (while pie supplies last) and awards to follow. There will be the Craft Fair that will showcase regional and local arts and crafts vendors and their spectacular works of art. Artists and crafters will be selling original pieces such as ceramics, quilts, jewelry, paintings, and other decorative pieces. The Fall Festival Craft Fair will be an event the whole family can enjoy with many types of art and handmade items on display.

Prices will vary by item and payment is made directly to vendors.

Enjoy the Bake Sale and attractions such as a Balloon sculpture, Pony rides, Arm Painting, Hay wagon rides, Pumpkin Decorating, Bouncy pony hop races, Cow Milking Contest, Hay bale mound, Arts and crafts, Photo opportunities, 9 Hole Disc Golf Course.

Winnequah Park, Winnequah Road, Monona

Annual Puptoberfest - A Day for the Dogs - Sunday, October 16, 12 PM – 5 PM

Come enjoy a day for the dogs at Wisconsin Brewing in Verona & help support OccuPaws Guide Dogs. FREE Admission to this dog-friendly event! Social and leashed dogs are very welcome. Live Music from the Red Hot Horn Dawgs!

Bring the whole family, both canine and human! There will be an "ask the dog trainer" tent, microchipping and nail trims, and a fun craft & vendor area where you can find great items for both yourself and your favorite furry friends. But don't worry if you don't have a dog, as there will be something for everyone. An amazing lunch will be available, and of course, great beer from Wisconsin Brewing!

Wisconsin Brewing Company, 1079 American Way, Verona

Halloween at the Farm - Saturday, October 22, 4 PM – 8 PM

Spooky Fun for the Whole Family: at Schumacher Farm Park!

Attractions include: Interactive characters, Marshmallows at the campfire, Storytelling, Fortune telling, Old Fashioned Games and Crafts, Hay Rides throughout the event, Live Music in the Historic Barn, Face Painting & Tattoos.

Concession Stand with simple food such as hot dogs, hot cocoa, cider, and baked goodies.

Tickets can be purchased at the Farm!

Schumacher Farm Park, 5682 WI-19, Waunakee

Hayride around the Capitol Square - Wednesday, October 26, 3 pm - 6 pm

An afternoon of Halloween family fun at Downtown Madison Family Halloween! Take a hay wagon ride around the Capitol Square and see the movie Hocus Pocus at the top of State Street!

Meeting Location: approx. 12 N. Carroll St., in front of Grace Episcopal Church.

Duration and Route: Approximately 20 minutes around the Capitol Square.

Last Boarding: 5:40pm

Seating Capacity: Approximately 24 people, adults & children.

100 Block of State Street, Madison

Family Halloween - Wednesday, October 26, 3 - 6 pm

Halloween fun for families and kids 12 & under! Special Kids in the Rotunda shows and festive Halloween photos at the Overture Center, Madison Parks Hay Rides around the Capitol Square, crafts, art projects, stories and songs, trick or treat at 75 participating businesses, and more!

State Street & Capitol Square

Cambridge Halloween Parade & Trick-or-Treat Trail - October 29, 10 AM - 12 PM

Children of all ages (and their families) are invited to show off their Halloween costumes for the parade around Veteran’s Park in downtown Cambridge, followed by a “Trick or Treating Trail” where kids can trick or treat downtown businesses!

Want to get in on the fun? Meet in the parking lot behind Badger Bank at 9:45 am to line up to walk in the parade. The parade will begin at 10:00 am, starting from the Badger Bank parking lot on Spring St, heading to North St, and then Park St. The parade route is about 2.5 blocks long making it an easy distance for little legs and kids eager to get their hands on some candy!

At the end of the parade, kids will pick up a “Trick or Treating Trail” map letting them know which downtown Cambridge businesses are participating in Trick or Treating, and then they’re off!

102 W. Main Street, Cambridge

Main Street Trick or Treat - Monday, October 31, 3 PM – 5 PM

Verona Area Chamber of Commerce is once again hosting the Main Street Trick or Treat event! Come out to Main Street Trick or Treat, where Verona businesses and organizations are excited to see great costumes and hand out truckloads of candy and treats! Main Street Trick-or-Treat stretches between West Verona Avenue and ends just past Verona Vision Care. Any business not located on Main Street can set up a tent and table at Hometown Junction Park. Get candy and snacks all from downtown Verona Businesses!

Come get candy and cookies from the Hansen Home Team right across from the park as well!

Main St. Verona, ending at Hometown Junction Park, 101 W. Railroad St.

Pumpkin patches - Open through the season

Pumpkin patches are a staple part of fall activities! The best place to get a good carving pumpkin is out with the family at a local farm. Here are a few around Southern Wisconsin that have pumpkins, snacks, and some kid's activities!

  • Schuster's farm - 1326 US-12, Deerfield

  • Sutter's Ridge Farm - 2074 Sutter Dr., Mt Horeb

  • Appleberry farm - 8079 Maurer Rd, Cross Plains

  • Treinen Farm Corn Maze and Pumpkin Patch - W12420 WI-60 Trunk, Lodi

  • Hermanson Pumpkin Patch - 127 County Highway N, Edgerton

  • Anderson’s Pleasant Patch Pumpkins - 2313 Koshkonong Rd, Cottage Grove

Apple orchards - Open through the season

Like pumpkin patches, apple orchards are another staple fall activity! Check out these great farms in the Southern Wisconsin area for all your apple picking needs.

  • Schuster's farm - 1326 US-12, Deerfield

  • Appleberry farm - 8079 Maurer Rd, Cross Plains

  • Hawks orchard - 9034 N Serns Rd, Milton

  • Alpine ridge orchard - 5610 Alpine Rd, Brooklyn

  • Auntie Evie’s Apple Orchard - 18900 W National Ave, New Berlin

  • Lapacek's Orchard - N1959 Kroncke Rd, Poynette

Don't be sad that summer has come to an end. The local events are still happening! We hope these fall activities and events spark some seasonal joy, and get the family excited for the temperature to drop! Let us know if you went to one of these events, or which one sounds the most fun!


bottom of page