Midwest Road Trips Perfect for Fall Break
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It seems like every day there is a new headline about flight delays, layovers, or worse - cancellations.
Fall break should be a time for your family to recharge after the back-to-school rush and before the busy holiday season. Cut out airline uncertainty, break out the old atlas (Millennials, you know what we’re talking about), and take a road trip!
We’re diving into some of the Midwest’s most drive-worthy spots and giving you pro trip tips along the way - so buckle up - because it’s time to go:
1. Hard Truth Distilling Co., Nashville, IN
Tucked away in an unassuming corner of lush Brown County is the village of Nashville. The downtown is filled with plenty of locally owned shops touting everything from antiques to handmade soaps as well as art studios and galleries. It’s also home to Hard Truth, a premier craft distillery destination located just outside the Nashville city limits. During a recent visit we loved getting to know the Hard Truth campus and diving in to all they offer including mixology classes, distillery tours, delish dining, outdoor music (peek their incredible Terrace below!), extensive drink menu including Fall faves maple bourbon rum, and more.
Road Trip Tip: Don’t underestimate the power of grocery bags, paper towels, and baby wipes on a long drive with kids of all ages.
The Hard Truth Cabin is available to book for ages 21+.
Hard Truth also recently added a rentable 2-bedroom cabin, nestled off the main campus drive. Here you’ll discover sleeping arrangements for 4+ in a modern-House-Beautiful-meets-rustic-vibe, complete with SMEG fridge, trails that meet the back door, and plenty of room for indoor and outdoor fun. You also can’t beat having the main Hard Truth amenities within walking distance.
More must-dos for you:
Adults-only fun: The Whole Truth tour through the working distillery or Get Lost ATV tours
With the fam: Venture to Brown County State Park with trails for the kids to explore while you admire fall leaves, then head over for dinner at Hard Truth.
2. Traverse City, MI
Imagine a bustling city bursting with cultural fun. Now surround that with breathtakingly gorgeous beach towns. And finally, consider grand sand dunes, state forests, and an outdoor paradise wrapping all of those in a hug… that is the Traverse City region of Michigan. Home to countless miles of trails, rivers, apple orchards, wineries, and Lake Michigan shore, Traverse City will always leave visitors wishing they had more time to share. In Fall this area comes alive with activity - Star Parties at Sleeping Bear Sand Dunes (a national lakeshore property managed by the National Parks Service), kayaking in Crystal River, and the Hunt for the reds of October wine trail progressive. But don’t forget to leave room for a drive along M-22 - often referred to as the most beautiful road in the state, where Fall colors are certain to pop.
Shopping in surrounding Suttons Bay, Leland, and downtown Traverse City is a must as well. Top off your time with a stop at Little Fleet, an outdoor beer garden with food trucks or grab a little chocolate from Grocer’s Daughter in Empire. Visit our friends at Traverse City Tourism for more suggestions.
Overlooking the Sleeping Bear Sand Dunes.
Road Trip Tip: Traveling with younger kiddos? Plan ahead for stops that include parks or play spaces to get wiggles out!
Image Credit: @traversecitytourism
More must-dos for you:
Adults-only fun: Visit the wineries of Leelanau Peninsula during their Hunt for the Reds of October wine series or try a Fall carriage ride at Black Star Farms.
With the fam: Enjoy the nautically-themed Great Lakes Children’s Museum or try this new, self-guided scavenger hunt (complete all and receive a free piece of pie from the Grand Traverse Pie Co!)
Image credit: Go To Louisville CVB
3. Louisville, KY
Looking for the perfect urban Midwestern getaway with tons to do? Let’s talk Louisville. From Waterfront Park to the Louisville Slugger Museum tour, there’s always a place to play and Louisville is especially fun in October. Halloween lovers will delight in Halloween on Hillcrest, a (free!) hidden gem of amazing yard decorations and family-friendly spooky fun. Iroquois Park boasts of the Louisville Jack O’Lantern Spectacular, a trail of elaborate, hand-carved pumpkins. And though fall may bring cooler temps, it’s hard to say no to ice cream in any season, so be sure to head over to The Comfy Cow for a treat!
Image credit: Go To Louisville CVB
Road Trip Tip: Save money and time by packing plenty of snacks, drinks, and even lunch!
Louisville Jack O’Lantern Spectacular (Image Credit: Danita Delimont, Getty Images)
More must-dos for you:
Adults-only fun: Book a stay at the iconic Brown Hotel, or plan a bourbon tasting
With the fam: Check out the Louisville Mega Cavern - a former limestone mine and cave - complete with underground zip lines, mountain bike park, and more.
4. Chicago, IL
Chicago and Fall break fun go hand-in-hand, especially with iconic spots like the Shedd Aquarium, which is home to everything from beluga whales to sea otters. You’ll definitely want to take in a tour at historic Wrigley Field or, if you’re lucky and the Cubs are still in-season, a game. For a unique (and less crowded) view of the town, grab a seat on one of the many architecture tours on the Chicago River. Of course shopping on the Magnificent Mile is a must.
With kids in tow, let them explore the many hands-on exhibits at the Museum of Science and Industry. And no visit to the Windy City is complete without incredible food. Who better to break down the family-friendly grub spots than our friends at Chicago Parent? Peek their list here.
Image credit: @maggie.daley.park on Instagram
Embark on a fall river cruise in the Windy City (Image shared with thanks to Choose Chicago)
More must-dos for you:
Adults-only fun: Catch a show at the famed Second City
With the fam: Stop by the incredible 20-acre, public Maggie Daley Park in the Loop and enjoy the Play Garden or Climbing Wall
Image credit: @sarahavituaphotography via @DoorCounty on Instagram
5. Door County, WI
If spectacular fall foliage and an outdoor adventure are what you seek, Door County claims to have the best leaves in Wisconsin. Check out their fall report here for up to the minute leaf news, or their guide to wineries, breweries, distilleries, and cider houses if you’d like to sample some local beverages. Up for some final outdoor adventures before winter hits? With over 300 miles of shoreline, the water sports in Door County are a can’t miss - see all the info about kayaking, boating, and fishing here. Two more iconic attractions to check out: Cana Island Lighthouse, and the Skyway Drive-In Theatre.
Image credit: @daneggertphotography via @DoorCounty on Instagram
Road Trip Tip: Traveling by electric vehicle? Map out your charging stops ahead of time so you’re not scrambling on the road. We like Plugshare for this!
The welcoming fire pit at Somerset Inn, Door County, WI (Image Credit: @doorcounty)
Photo credit: Mackinac Island Tourism
6. Mackinac Island, Michigan
We’ve shared lots of love for Mackinac Island including why it makes the perfect Fall getaway for families, to 10 things to do with kids during your visit. From the 80+ miles of trails to the car-free environment, this eclectic island is the perfect getaway. But take away the bustling crowds of Summer and add in some Fall color, you have all the right reasons to whisk your fam away for an autumnal adventure. The Mackinac Island Tourism Bureau always shares the skinny on things to do while on Island time. And while the Island boasts many spots for lodging, we’re partial to the Mission Point Resort.
Cars are not allowed on Mackinac Island, requiring guests walk, use bikes, or take a horse taxi for transport.
7. Red River Gorge, Kentucky
Known for its stunning natural beauty, towering sandstone cliffs, unique rock formations, and over 100 natural sandstone arches, Red River Gorge is a popular destination for outdoor enthusiasts, offering activities like hiking, rock climbing, zip-lining, and camping. Overnight guests will love the nearby cabins available for rental, or amp up your experience with a yurt.
While trekking through the Midwest may not always be the most exciting way to spend a day, these destinations and the time spent traveling with loved ones (without wifi), make the journey so worth it. We wanna know - where are your fam’s fave spots to stop?
Looking for more Fall break inspo in the Midwest? Check out these 10 unique AirBnBs!
