This fall, you deserve more than just the occasional pumpkin spice latte: You deserve a full weekend getaway taking in the foliage at one of the Midwest’s most colorful autumnal destinations.
So grab your best layering sweater, throw your best apple-picking basket in the car and head towards one of our top pick destinations to enjoy the season.
Cartier Mansion Bed and Breakfast
Ludington, Michigan
If you prefer your autumn leaves with a side of century-old manors, then the Cartier Mansion is the place to head this fall.
Originally built in 1905, the mansion is listed on the National Register of Historic Places and has been meticulously preserved over the years. The Mansion features comfortable, unique rooms, incredible breakfasts (their signature Baked Oatmeal Bananas Foster is worth the trip alone) and — best of all — your dog can join in on the fun too. (Read the Cartier Mansion’s pet policy before you pack Fido up here.)
Where to Enjoy Fall Around Town: While Ludington may be best known as a beachside summer favorite, there’s no shortage of fall activities, too. Hop in the car and follow Ludington’s official Fall Color Tour here, but don’t miss Historic White Pine Village, a historical reenactment town with locally made ice cream, and Orchard Market, which has been family-owned since 1960. Before you head back up to your mansion, grab dinner at Table 14, an upscale Southern restaurant with an equally upscale cocktail menu.
Story Inn
Nashville, Indiana
Once upon a time, Story, Indiana (see what we did there?) was a bustling community, supporting two general stores, a schoolhouse and everything else a busy 1800s town could need. But as the population moved elsewhere, the town was all but abandoned — until the Story Inn opened up.
The Story Inn is a completely unique hotel experience where guests stay in one of 14 beautifully renovated rooms, all of which sit in former Story buildings, making it your once-in-a-lifetime opportunity to sleep in a former one-room schoolhouse.
And you definitely won’t want to miss dinner at the inn’s renowned restaurant, with special prix fixe dinner service, available Thursday through Saturday, with wine pairings available.
But leave your work computer at home — the accommodations don’t have Internet, televisions, alarm clocks or phones, and the remote setting makes cell service spotty, so tell your boss you’ll ping them when you’re back.
Where to Enjoy Fall Around Town: The Story Inn is practically surrounded by Brown County State Park, the largest park in Indiana. At 16,000 acres, the park has the nickname “the Little Smokies” because of its resemblance to the Great Smoky Mountains, with around 20 miles of tree-lined roads and scenic vistas to get all the #autumn photos you can handle.
Before you head back up to your hotel for the night, be sure to visit one of Nashville, Indiana’s six wineries and distilleries, including the award-winning Brown County Winery.
The Merrill Hotel
Muscatine, Iowa
Overlooking the Mississippi River, The Merrill Hotel is a 4-Diamond Boutique Hotel located right in the picturesque heart of Muscatine, Iowa. With 122 guest rooms, the hotel’s amenities include a heated indoor saltwater swimming pool, a large fitness center and the on-site Maxwell’s On the River, a restaurant with an emphasis on local, sustainable food.
Where to Enjoy Fall Around Town: Get your fill of the great outdoors at Wildcat Den State Park, which has everything from sandstone bluffs to natural rock formations to *chef’s kiss* fall colors. From there, head over to the Environmental Learning Center, a 10,500-square-foot facility with expansive exhibits on Iowan wildlife, aquariums filled with native fish and even an outdoor raptor enclosure. Complete your day at Contrary Brewing Company, which offers 20 total taps and outdoor fireplaces for extremely cozy vibes. And before you head out of town, don’t miss the town’s National Pearl Button Museum, if only to cross it off of your bucket list. (Trust us — it’s actually worth the stop.)
DeSoto House Hotel
Galena, Illinois
The DeSoto House is one of the oldest operating hotels in Illinois, and from the moment you step inside, you’ll feel like you’re back in its early days. The hotel’s 55 guest rooms are each decked out in unique Victorian-style decor, and all of the rooms are named after a famous person who visited the city. (And, after your trip, it’s only a matter of time before they name a room after you too.)
The DeSoto House also offers three restaurants — including the Courtyard Restaurant (located in a four-story atrium), the Green Street Tavern and the casual fine dining Generals’ Restaurant.
Where to Enjoy Fall Around Town: Galena has long been a favorite weekend destination for Chicagoans, and with a charming downtown surrounded by so much nature, it’s immediately clear why. Spend a few hours checking out downtown Galena’s seemingly endless rows of boutiques and art galleries, and then head to West Street Sculpture Park to see some fall colors with a side of art. From there, swing by the Old Blacksmith Shop, a combination museum and working blacksmith foundry. (Admission is just $5, but spending the rest of the day wondering if you should switch careers and become a blacksmith is free.)
On your way out of town, be sure to stop by Orchard Landing Apple Farm, located on a private airfield — so you can have your private jet pick you up when you’re done.
Hotel Retlaw
Fond Du Lac, Wisconsin
The award-winning Hotel Retlaw originally opened in 1923 and was re-imagined in 2019, giving visitors the best of both worlds. With an on-site farm-to-table restaurant, a fitness center and a prime location in downtown Fond Du Lac, you may just want to spend a perfect autumn weekend hanging out in your hotel.
Where to Best Enjoy Fall Around Town: In true Wisconsin fashion, Fond Du Lac is surrounded by endless outdoor activities, but you can’t go wrong with a trip to Kettle Moraine State Forest, with 100 miles of hiking, biking and nature trails and 22,000 acres of kettle lakes, prairies and forested glacier hills.
Don’t know what a forested glacier hill is? (Neither do we, to be honest!) After you see all of the leaves, head to the Ice Age Visitor Center, where you can hear about the area’s incredible history. Complete your night with a trip to Cellar District — a renowned restaurant housed in a former church, complete with stained glass windows. On your way out of town, grab a snack for the road in the form of a 12,000 pound wheel of cheese at Henning’s Cheese.
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