5 Fabulous Fall Festivals in the Midwest

Alamo Travel Tips - 5 Fabulous Fall Festivals in the Midwest - Get details on five fabulous fall festivals across the Midwest and other travel advice from Alamo Rent A Car.

With the weather cooling down, leaves changing colors and pumpkins in full display, autumn has officially arrived. The change in season brings many fall festivals, complete with fun for the whole family. Here are five fabulous fall festivals you can find throughout the Midwest:

Map of 5 Midwest Fall Festivals Map of 5 Midwest Fall Festivals

Pony Express PumpkinFest

Oct. 11-13, St. Joseph, Missouri

PumpkinFest Great Pumpkin Mountain PumpkinFest Great Pumpkin Mountain. Photo by Saint Joseph Missouri, Flickr.

Located about an hour north of Kansas City, Missouri, St. Joseph is best known as the starting point of the Pony Express mail service and the place where the infamous outlaw Jesse James was killed. Its Pony Express PumpkinFest takes place at the Pony Express National Museum. On opening night, you can watch the lighting of the Great Pumpkin Mountain, where hundreds of carved pumpkins light up with just the flip of a switch! The festival also features live entertainment, a children's costume parade, crafts, food and festival rides and games.

Florissant Fall Festival

Oct. 13, Florissant, Missouri

On the other side of Missouri in the St. Louis metro area, the Florissant Fall Festival attracts tens of thousands of visitors to historic Old Town Florissant. The festival features a wide range of activities, including a dog show, music, a craft fair, a flea market, plenty of food, a car show and historical displays. For kids, there will also be pony rides, wagon rides and games.

Stillwater Harvest Fest

Oct. 12-13, Stillwater, Minnesota

Stillwater Harvest Fest Giant Pumpkin Piñata Smash Stillwater Harvest Fest Giant Pumpkin Piñata Smash. Photo by Shawn Hogendorf, Stillwater Current.

Have you ever seen a 1,500-pound pumpkin? Just 30 minutes east of Minneapolis , the Giant Pumpkin Weigh-Off at the Stillwater Harvest Fest touts the largest pumpkins in the region, along with a giant pumpkin boat race and pumpkin drop. The Harvest Fest also features a pie-eating contest, a chili cook-off, a tractor pull and live music. For adults, there's microbrew beer and wine tastings, and kids can enjoy a costume parade and other kids-only activities.

The Halloween Gathering Festival and Parade

Late October, Chicago, Illinois

Halloween Gathering Festival Parade Halloween Gathering Festival Parade. ©Chicago Cultural Mile Association, photography by Sheri Whitko.

Tap into your artistic nature and the magic of the season during the Halloween Gathering Festival and Parade on Chicago’s Cultural Mile. During the day, festival-goers can see live performances, art installations and take part in craft and movement workshops in Millennium Park and Sir George Solti Garden. Kiddos can also show off their creativity during the kids’ costume procession. At dusk, events move to Columbus Drive, from Balbo Street to Monroe Street, for the spectacle parade. Led by 13 Creative Spirits and filled with artful performances, incredible costumes, music and more, this parade embodies the imagination of the entire festival. Both day and evening festival events are free and open to the public.

Sycamore Pumpkin Festival

Oct. 23-27, Sycamore, Illinois

Sycamore Pumpkin Festival Display Sycamore Pumpkin Festival Display. Photo by Sycamore Pumpkin Festival Committee.

About an hour and a half west of the hustle and bustle of downtown Chicago is Sycamore, Illinois, home to the Sycamore Pumpkin Festival. The festival was started by Wally Thurow — better known as Mr. Pumpkin to Sycamore residents — back in 1956. This year, the festival features a huge decorated pumpkin display of about 1,000 pumpkins, teen and kiddie carnivals, two craft shows, a pie-eating contest and a parade to conclude the festival.

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