Family-Friendly Fall Getaways Worth the Drive from Chicago

These fun vacay spots make us so excited for fall.

Autumn offers a chance to peep colorful foliage and explore outdoors before winter beckons us all inside. 

Take advantage of crisp sweater weather and the long fall holiday weekends. Whisk your little pumpkins to one of these family-friendly destinations to harvest some good times amongst the falling leaves.

Silver Lake Sand Dunes, Michigan

Photo credit: Cortney Fries

Refresh your senses in Silver Lake Sand Dunes where your squad can take a family-friendly natural rollercoaster ride through vast acres of sand dunes lining Lake Michigan with Mac Wood’s Dune Rides. The guides are hysterical and the exuberant experience is sure to leave you all smiling. There’s also a pedestrian area of the dunes that is beautiful for pictures. After your adventure, treat your crew to a huge sundae served on a frisbee at Whippy Dip.

Oh my gourd, you’re going to love Lewis Adventure Farm & Zoo. This sprawling, fifth-generation family farm, market and petting zoo features animal encounters and more than 46 activities (including tractor pulls, bouncing pillows, slides and games). Stay at the Dunes Waterfront Resort where you can enjoy spectacular sunsets over Silver Lake and walk to numerous family-friendly attractions. There are also several campgrounds and cabin rentals nearby.

Capture more wows at Craig’s Cruisers Family Fun Center with go-karts, mini golf, bumper boats, a whirly coaster and zipline. Silver Lake Chicken Shack is the place to go for juicy chicken wings and live music.

Micro-farm B&B in Union Pier, Michigan

Photo Credit: Cortney Fries

Make dreams of waking up to farm-fresh breakfasts come true at Goldberry Woods, a micro-farm bed and breakfast in Union Pier. Rent a family suite at the inn (which feature gorgeous tree branch bed frames) or a full cottage, and be amongst chickens, ducks, gardens and greenery galore. Kids will love the large, heated pool and bubbling hot tub. Hike or kayak alongside vibrant fall colors, buy veggies and artisan gifts from the camper-turned-market-stand and snuggle around the firepit before bedtime.

Explore beautiful Harbor Country at a relaxing pace. If you’re saying “autumn leaves and pumpkins please” Dinges Fall Harvest is sure to be your jam with a pumpkin patch, corn maze, hayrides and games. Apple picking, breweries and wineries, colorful sunsets at the beach, farmers markets and music in the parks will provide all the fall feels. Enjoy the relaxing ambiance of Brewster’s Italian Café while dining on wood-fired pizza, inventive drinks and salads like the Italian Sweet Corn.

Outdoor fun in South Bend, Indiana

Photo Credit: Cortney Fries

“The Bend” is home to the University of Notre Dame, which is super fun when fall football season is in full swing. Howard Park features an expansive, imaginative children’s playground with climbing structures, huge slides, swings and so many cool features my 10-year-old daughter was running with excitement. Grab a meal and even food for your pup at Howard Park Public House, located right in the park. See multi-color River Lights illuminating the St. Joseph River at night or ice skate in the park in winter.

Dine al fresco in the exquisite gardens of Carriage House where they serve wood-fired pizzas, burgers, salads and fresh seasonal drinks. Rum Village Aerial Adventure Park is the place for climbers ages 7 and up to get their adventure on with up to five obstacle courses in the trees.

Animal lovers will fall for Potawatomi Zoo. Chocolate cherishers won’t be able to resist South Bend Chocolates’ creamy seasonal treats. Pick pears and plums in September and apples in October at Lehman’s Orchard, just over the Michigan border. Visit Thistleberry Farm for pictures of your pumpkins in the patch, a cow train ride and more.

We stayed at the Holiday Inn Mishawaka, which is about 15 minutes from downtown South Bend, near the Mishawaka Riverwalk and Strikes & Spares bowling, go karts and ninja course. The hotel is clean, modern and has a pool.

Driftless Region, Wisconsin

Unwind at a dog-friendly, third-generation family farm bed and breakfast. Justin Trails Resort, a 200-acre farm with gracious hosts, lets you devour scratch-made morning meals, feed llamas, explore the hilly grounds to see incredible fall foliage, play disc golf and then soak in a whirlpool tub (offered in most cottages and suites). 

While there, drive to historic downtown La Crosse for quaint shops, restaurants and treats. My daughter loved the La Crosse Community Theater, where you can see Fiddler on the Roof this fall. Riverside Park is a picturesque place to play along the Mississippi River. Grandad Bluff offers scenic views of the Driftless Region, especially sensational when quilted with crimson and burgundy. 

Door County, Wisconsin

Photo Credit: Cortney Fries

In northeast Wisconsin, Door County is gorgeous dressed in autumnal oranges and fiery reds and offers a plethora of outdoor activities and family-friendly attractions. Five state parks with vertical sandstone bluffs and numerous historic lighthouses beckon exploration. Savor the bounty of the harvest with Wisconsin cheeses, cherry jams and pies, and other treats in addition to fall favorites.

Enjoy autumn festivals like the Egg Harbor Pumpkin Patch or a Cider Press Party. Bottle feed baby goats and watch chicks hatch at The Farm. Take a hike at Peninsula State Park, where the observation tower offers stunning views across the bay and is accessible for strollers and wheelchairs.

Kayak the glassy, clear waters of Cave Point County Park. Peninsula Kayak Company will guide you to caves and other geological wonders. Get a lay of the land and hear some local lore on a family-friendly Door County Trolley Tour. Pick a peck of apples and sip wine and cider at Lautenbach’s Orchard. Walk through the water or ride a hay wagon to visit Cana Island Lighthouse. Climb 97 steps up a spiral staircase for a bird’s eye view across the peninsula.

Take in the tradition of a Door County fish boil at White Gull Inn. Watch whitefish and potatoes cook over an open flame, then seal the meal with a slice of tart cherry pie and ice cream. Swedish pancakes with lingonberries and Swedish meatballs are sure to be savored at Al Johnson’s Swedish Restaurant & Butik. The kids will get a kick out of the goats grazing on the roof.

Wilson’s Restaurant and Ice Cream Parlor has been a hit since 1906 with its soda fountain, juke box and burgers.

We stayed at Bailey’s Harbor Yacht Club. On the shore of Lake Michigan and only a mile from restaurants and attractions, this secluded condo resort features pools, games and bike rentals.

Traverse City, Michigan

Photo Credit: Traverse City Tourism

Leaf peepers unite! TripAdvisor has named gorgeous Traverse City, Michigan, one of the best fall foliage destinations. Take in the fiery reds, blazing oranges and sunny yellows on the Pierce Stocking Scenic Drive, then go for a hike in the outdoor playground that is Sleeping Bear Dunes. Climb the towering sand dunes and soak in the rewarding, blue views of Lake Michigan 450 feet below.

Gallagher’s Farm Market and Bakery is a family-run farm with a pumpkin patch, corn maze, steamy cider and pumpkin doughnuts. Pahl’s Pumpkin Patch and Country Store in nearby Buckley is also a great place to harvest your fall family memories. This working farm features U-pick pumpkins, wagon rides, barrel train rides and ponies. You can purchase treats as well as Pahl’s fresh meats from the country store.

Great Lakes Children’s Museum is a fantastic place for kids ages 8 and under to have some indoor fun. Scoop up some smiles no matter the weather at Moomers Homemade Ice Cream. Craft brews and regional wines abound in Traverse City for parents who wish to partake.

Cedar Point and Shores & Islands, Ohio

Photo Credit: Cedar Point

Fall is the perfect time to go to the “Rollercoaster Capital of the World” because it’s typically not too hot or crowded. Cedar Point, located in Sandusky, Ohio, is open through the end of October. There you’ll find all the thrills your family could possibly ask for, with 70 spellbinding rides, including 18 world-class roller coasters.

My daughter and I rode Millennium Force, voted the best steel coaster in the world. It goes crazy high (up 300 feet) immediately upon take off, reaches speeds up to 93 mph and is insane fun. We couldn’t stop grinning. More tame options include Gemini, the racing coaster, and Cedar Downs, the derby carousel. HalloWeekends offers up haunted attractions to get you in the Halloween spirit.

Stay at beachfront Hotel Breakers, next to Cedar Point, and enjoy discount tickets to the park as well as early park entry. Shores & Islands is a fun area to explore, especially Put-in-Bay, which you can visit via Miller Ferry. There, rent a golf cart or see the sites on a train tour. Families enjoy classic entertainment like mini golf, a butterfly house, cave tour and merry-go-round. Most Put-in-Bay attractions are open weekends through mid-October.

Galena, Illinois

Photo Credit: Illinois Office of Tourism

Galena offers picturesque, panoramic views of three states (Illinois, Iowa and Wisconsin). It’s a small town with a rich history (Ulysses S. Grant’s Home is there) and rolling hills that are fun to hike and candy for the eyes on crisp, clear days. Glide down the Alpine Slide weekends through early October. Go horseback riding or spook yourselves on a ghost tourOktoberfest is fun for families with wiener dog races, polka dancing, bounce houses and pumpkin decorating.

Curious about goat yoga? Give it a try at Original Goat Yoga, Galena. Families are welcome, and it’s just as much about having fun relaxing with animals as it is about stretching your body with yoga. The goats are likely to jump on your back, lay on your mat and give you some snuggles. You can also take a hike with goats and bottle feed kids (baby goats) by a bonfire with Hoof It Goat Treks.

Kayaking, fishing and riding electric bikes are other adventurous ways to explore. Nuts Outdoors offers guided tours on electric bikes that make the hill climbs easy, can take you to some favorite fishing holes, or show you the best kayaking and wildlife viewing spots.

South Haven, Michigan

Photo Credit: Katina Beniaris

Quaint South Haven, Michigan, provides an idyllic fall escape. The Covert/South Haven KOA is a family favorite because it has cabins as well as tent and RV sites and tons of activities, such as a jumping pillow, trampoline basketball, crafts, movie nights and more. South Haven has a cute downtown with antiques and ice cream shops, a beach with lighthouse and sand dunes. St. Joseph, Saugatuck and Holland are also close by.

Farmers markets, microbreweries and the Kal Haven Trail are perfect to enjoy in the fall. Bike or hike the 33.5-mile trail from South Haven to Kalamazoo, across bridges and through adorable small towns, where you’ll feel the friendliness and warmth of the season. You can also visit Harvest Moon Acres in Gobles, which has corn mazes and farm animals.

Elizabeth, Illinois

Snooze in the color-changing treetops above Dittmar Farms in Elizabeth. The 600-square-foot lofted Arrowhead Treehouse sleeps six and is just steps away from the apple orchard and pumpkin patch. Talk about an autumn lover’s dream come true! Make a campfire with s’mores, watch the stars twinkle in the night sky and feel your cares melt away. 

During the day, pick apples, launch gourds, munch doughnuts, take hayrides and try not to get lost in the corn maze. Galena is only a 20-minute ride away where you can stroll historic Main Street and peruse more than 125 independently owned shops and restaurants. Great American Popcorn Co. makes Witches Brew popcorn and other flavors that are sure to put a spell on you. 

Marinette, Wisconsin

Photo credit: Travel Wisconsin

Families will love the beautiful scenery on back country roads or in the parks of Wisconsin. Take a look at its interactive guide to see the fall colors in Marinette. Make sure to take a drive to Marinette County’s Waterfall Tour and see 15 falls and cascades.

Take a boat ride on Menominee River to Stephenson Island. Here, you can enjoy seeing monuments, like The Soldier Memorial, going fishing, having a picnic or playing at the playgrounds.

Since Wisconsin is known for its cheese, you have to stop at Seguin’s House of Cheese before you head home. You can shop for fresh cut cheese, curds, strings, spreads, smoked meats, mustard, jams, sweets, moccasins and more.

Pewaukee, Wisconsin

When your kids are clamoring to splash in a water park and you don’t want to drive too far or hit the Dells, Ingleside Hotel is your answer. Springs Water Park offers 45,000 square feet of wet and wild fun with tube and body slides, a lazy river, indoor/outdoor hot tub, activity pool and children’s area. Stay in an Executive Suite where you can spread out and savor a tasty supper club dinner, such as bourbon roasted chicken or braised short ribs. Check the special events page on the hotel website for discounts and packages. 

Shipshewana, Indiana

Photo credit: Shipshewana/ Lagrange Co. Convention & Visitors Bureau

This trip is just a little over two hours long from Chicago. There is so much for families to experience in the autumn season here. Pumpkinvine Nature Trail is a must in October to see the pretty fall colors. You can take a walk or ride your bicycle down the paved path that goes from Shipshewana to Middlebury to Goshen.

Enjoy seeing the fall colors like the Amish on a Buggy Lane Tour. They even have an option for you to enjoy a buggy ride and a home cooked Amish dinner. Families can enjoy feeding the animals up close at Dutch Creek Animal Farm. Also, make sure to head into town for shopping and a pretzel at JoJo’s.

Fort Wayne, Indiana

If you love apples and history, visit Fort Wayne, Indiana, during the Johnny Appleseed Festival Sept. 16-17. Johnny Appleseed is buried in Fort Wayne along the St. Joseph Riverbank. Learn more about his life at this period-authentic festival full of entertainment and apples.

If your kids are older or lean more toward the scary side, plan your trip for Oct. 21 for the annual Fright Night. See 10,000 zombies parade through the downtown streets. Don your best zombie makeup, listen to ghost tales, dance to live music and trick-or-treat. It’s an easy Halloween event that is sure to keep the kids talking.

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Cortney Fries
Cortney Fries
An award-winning travel journalist, Cortney Fries (pronounced "freeze") has been writing about family travel for over a decade. She knows that parents planning trips are looking for all members to have fun and make lasting memories. Cortney believes that you should definitely try anything that makes you slightly nervous.
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