Halloween Celebrations Worth Traveling For

In the Midwest, larger-than-life Halloween celebrations rise up every October like the Great Pumpkin (or benevolent spooky spirit or two) to captivate guests with parades, caramel apples, costume contests, and more. Here are some of our must-see Halloween celebrations, including festivities in a town trademarked as the Halloween capital of the world and an event inspired by Native American lore.

Halloween Capital of the World, Anoka, Minnesota

Anoka calls itself the Halloween Capital of the World for good reason. Visit this Minnesota city for a month-long Halloween celebration that includes three parades (one with a 5k run), movie nights in the park, walking ghost tours, a pub crawl, and a juried pumpkin weigh-off that is taken very seriously by participants. The event began more than a century ago following a tempestuous season of shenanigans (like turning over outhouses and letting cows loose down Main Street); the city's leaders decided to keep residents occupied every October from then on. "In 1920, we had our first Halloween festival, which consisted of children parading down Main Street in costumes ending with a bonfire in the evening," says festival volunteer Karen George. Today that humble festival has grown into weeks of activities, but it still maintains its hometown flavor. Just try the caramel apples.

Jack's Pumpkin Pop-Up, Chicago

Jack's Pumpkin Pop-Up—geared to families during the day and adults in the evening—will check the boxes on many Halloween bucket lists (September 21-November 5, 2023). More than 10,00 pumpkins, a corn maze, axe-throwing, Instagram photo ops, fortune tellers, carnival games and treats like apple doughnuts await at Chicago's largest Halloween festival. Adults can enjoy seasonal beers, Halloween-inspired cocktails and spiked seltzers. Fall festival? Halloween-themed spookiness? Yes to both—this Halloween celebration has plenty to choose from. To keep the fun going outside the festival, check out Chicago-area hotels like The Drake Oak Brook, which is debuting Halloween Candy and Cocktail pairing menus this year as well as an evening Hocus Pocus High Tea served in a witch's cauldron.

Historic Irvington Halloween Festival, Indianapolis

A weeklong celebration now in its 77th year, the Irvington Halloween Festival has unexpected treats in store. Kicking it all off is a masquerade ball where masks and sparkling costumes are the norm (sold out for 2023; make plans early for 2024!). If that doesn't knock your socks off, try the Spooky Organ Concert, Horror Shorts Movie Night, Zombie Bike Ride, or an evening of seances. The final hurrah is a Street Fair and After Party on Saturday, October 28. This year's party theme is Alien Circus Encounter, so channel your favorite Martian because best-dressed guests win the most out-of-this-world prizes. But no worries if you don't take home the gold; the live music, light shows, and massive list of vendors are worth the trip.

Galena Annual Halloween Parade and Festival, Galena, Illinois

Galena's parade and festival, now in its 43rd year (October 28, 2023), is known for elaborate floats, marching bands, a food festival, kids' activities and costume contest. According to Tom Rynott, communications director, "One of the most captivating moments is our evening light display—hot air balloons illuminating the night sky—which adds a magical touch to the celebrations." Visitors are asked to bring nonperishable food items to donate to the local food pantry.

Windigo Fest, Manitowoc, Wisconsin

What's a windigo? According to the legends of the Algonquian-speaking native peoples from the Great Lakes region, it's a beast that was once human but is now a man-eating ogre. The Windigo Fest (October 6-8, 2023) exemplifies the dark side of Halloween; it's also the largest annual Halloween festival in Wisconsin, and a must-see for those who like a good scare—as well as just a good time. You'll come across celebrity guests from popular horror films, dancing witches, belly dancers, food vendors and musicians. Check out the art of pumpkin-sculpting, or take part in a paranormal journey with renowned researchers and investigators. Dawn Dabeck, president of the Windigo Society and Windigo Fest, recommends entering the raffles to win large Halloween props. If you're looking for an equally spooky spot to crash the night, she owns and runs Dead by Dawn Dead & Breakfast in Manitowoc— "a haunt-themed bed and breakfast where you don't get a good night's sleep." Either way, your stop in Manitowoc will be a scream.

Mackinac Island's Halloween Weekend, Mackinac Island, Michigan

This celebration (October 27-29, 2023) marks the last big weekend of the island's annual season, as businesses get ready to shut down for the winter. Halloween Weekend events take place throughout Mackinac Island including the Great Turtle Run (now in its 27th year), downtown trick-or-treating, live music, and adult costume parties. Stop by the many businesses saying goodbye for the season with parting gifts of Halloween goodies.

Conner Prairie's Headless Horseman Festival, Fishers, Indiana

Celebrating 40 years in 2023, his family-oriented festival (October 5-29, Thursdays through Sundays) features a 10-acre corn maze as well as haunted hayrides throughout Conner Prairie's grounds; a midway with amusements like the Spinning Apples ride and Monster Mini-Golf; a barrel train ride for the kiddoes; the Sleepy Hollow One-Man Show and Eerie-llusions Magic Show; and live music. Visit The Bizarre Bazaar for a tribute to the legend of the Headless Horseman.

Hallowe'en in Greenfield Village, Dearborn, Michigan

Put this on your calendar for 2024, because 2023 tickets are already sold out for Hallowe'en in Greenfield Village, held every weekend in October. "The event has evolved over the past 40 plus years to the 16-evening event it now is," says Jim Johnson, director of Greenfield Village. "Initially a member-only event, it has been a public event for nearly 30 years." Guests can experience a bewitching Greenfield Village after-hours at their own pace to check out highlights like the Main Street 1920s-era carnival side show, a 1913 Carousel with a period band organ playing Halloween favorites, street-food vendors, live music, and colorful costumed characters. Harvest markets and ghostly performances also enchant—not to mention a Halloween express to convey guests.

Soderstrom Castle Halloween, Peoria Heights, Illinois

Each year the owners of the historical Soderstrom Castle throw a party for trick-or-treaters. This year's light-and-music show starts on Friday, October 27, 2023 and continues through October 31. Trick-or-treating is available on October 31. The Peoria Heights house, built in 1930, was designed to look like a European castle, with turrets, Gothic arches and stone fireplaces; the abode feels perfect for Halloween. Keep an eye on their Facebook page for details.

More Midwest Halloween Events

Halloween spelled backwards? Well, that would be Neewollah, the largest annual festival in Kansas; visit the small city of Independence October 20-28, 2023, for parades, a scarecrow contest, live music, fun run, BBQ cookoff and more.

The Trail of Scarecrows in Fairfield County, Ohio, plays off the county's reputation as the Scarecrow Capital of Ohio. More than 250 scarecrows created by local businesses, organizations, and individuals decorate the area; see them any time during October, using the Visit Fairfield County app to locate scarecrows and vote for your favorite.

Garden of Villains, in collaboration with the Hall of Heroes Superhero Museum, channels the darker side of the Marvel Universe in Elkhart, Indiana on October 6-7, 2023.

It's no surprise that Deadwood, South Dakota, would have a special Halloween celebration—DeadWeird (October 20-31, 2023). Highlights are a Monster Ball, Costume Contest (with more than $10,000 in cash and prizes!), spooky candlelight tours of the Broken Boot Gold Mine, family-friendly trick-or-treating, and a KidWeird Halloween event in the Deadwood Mountain Grand Event Center.