Harvest festivals, cider tasting, and crunchy forest trails. We’re loving the cool fall evenings and rediscovering our local parks in their new finery—with the top Midwest vacations for some autumn splendor and fun fall activities.
Best Midwest Vacations In The Fall
This roundup includes small towns with lively hearts and big, bold cities where anything goes. In the fall, these places offer up colorful landscapes (whether they’re urban or rural) plus a range of festivals and events themed for the autumn season.
Whether you favor compact cabins, stylish condos, or multi-story townhouses, book yourself a rental home on FlipKey to come back to after a day of autumnal adventures. Rentals make sense in terms of cost, space, and independence, meaning you end up with a great Midwest vacation trip that’s tailor made for you.
Here’s our 10 top towns and cities in the Midwest where you can pick a pumpkin, try a tasting, and see some fantastic seasonal scenery.
“Everything was there. The kitchen was fully stocked with pots, pans, cups, glasses, plates, etc. Bedrooms/bathroom clean as can be. It was like coming into your own home.” — FlipKey Reviewer
Book yourself a cabin and set out to enjoy fall in Hocking Hills. Kick off at Old Man’s Cave, named after a local hermit who made this spot his home, and take advantage of the area’s excellent hiking terrain. Swing by the Circleville Pumpkin Show, with its parades, contests, and stalls selling all the pumpkin-based foods you can think of, and then some.
Kansas City offer several fall festivals and events. If you’ve got the family in tow, check out the Great Pumpkin Fest at the Worlds of Fun amusement park, where there’s a hay bale maze and kids’ pumpkin patch. You could also try Kansas City Zoo for beer and wine tasting, Halloween-themed events, and of course, plenty of animal fun.
Stay in this quiet mountain town and you’ll have the fall foliage of the Black Hills National Forest right on the doorstep. Climbing, hikers, motor-bikers—they all come here to enjoy Custer’s historic center and the views from the roads and trails around it. Make sure you seek out the passageways and caverns of the Jewel Cave National Monument and the iconic profiles of Mount Rushmore.
Start at Geisler Farms, with s’mores over a fire pit, then pick your way through the corn maze, and choose your own pumpkin to take home. Des Moines has more than 800 miles of trails to explore on foot or by bike, leading you around the city’s fall foliage and further out into the glorious Iowa countryside.
Start your tour of Galena boating down the mighty Mississippi River, watching leaves on the turn, or fishing for bass and catfish. You might prefer the aerial view from a hot air balloon with Galena on the Fly, or the arts and crafts at Galena Country Fair, amid the gorgeous autumnal setting of Grant Park. In the evening, try Matthew’s Haunted Pub Crawl for a ghostly local tour washed down with a few drinks.
“Our condo worked out perfectly for us for the vacation. We loved having the water park on site! Everything was very clean and any request we made was addressed very quickly. Would highly recommend!” — FlipKey Reviewer
The Waterpark Capital of the World is understandably popular year-round, but there are plenty of other things to do here. In the fall, board Dells Boat Tours to appreciate the beauty of the Wisconsin River and the Dells rock formations. The views are arguably even better on the sunset cruise, which comes with dinner provided. This is also a good time of year to zipline through the treetops and see those changing colors up close.
This lively college town has plenty in store in the autumn. Begin with a self-guided tour of Matthaei Botanical Gardens and Nichols Arboretum, bursting with shrubs and trees, and truly breathtaking at this time of year. Nearby Dexter hosts the Apple Daze festival, with hayrides, a pie-eating competition, and plenty of cider to toast the new season. Lest we not forget the main draw in Ann Arbor: The University of Michigan football team. Experiencing a game at the Wolverine’s stadium—the largest in America with a capacity of 111,000 (!) people—is a memorable experience.
“This property has everything you could need, including anything you might have forgotten. The atmosphere is lovely… We rented bikes from the owner, picnicked in the backyard under the sunshade, walked to groceries, restaurants, and coffee, biked to the beach.” — FlipKey Reviewer
Don’t miss the lovely Minnesota Landscape Arboretum, with its seasonal scarecrows, Sensory Garden, and Pumpkin House. If you’re already getting into the Halloween spirit, you might want to bag a ticket for October’s Zombie Pub Crawl, where you’ll be able to taste the best of the excellent Minneapolis craft beer scene (in full zombie garb).
Warm days, cool nights, and leaves crunching underfoot. This is a great time to book a rental in Traverse City, where you’ll find entertainment in the museums and casinos, and plenty of fall color around the inland lakes and on the sweeping drives from winery to winery. Taste farm-to-fork flavours at a local restaurant, catch your own meal from a fishing boat, or take off on a biking excursion among gorgeous autumn scenery.
“We loved everything about this place. It was in a perfect spot—not far from town, but out of the craziness. The owner was great to deal with, the place was very clean, and it felt like a home away from home! Beautiful setting and backyard, and everything we could possibly need was provided.” — FlipKey Reviewer
By day, admire the colorful landscapes of Brown County, catching the changing leaves of Yellowwood State Forest and Brown Country State Park. In the evening, you can see a bluegrass show, grab a first-rate Nashville dinner, and round the night off in a hot tub.