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Head to Wisconsin for Real Pumpkin Farms and the Osthoff Resort

Make the most of your pumpkin excursion

Photo: Alicia Petrie

You could keep taking the kids to one of the so-called pumpkin farms around Chicago—many are more carnival than farm—or take a quick fall trip to Elkhart Lake, Wisconsin, for an authentic pumpkin farm getaway. Here’s how to do it.

Check in at the Osthoff Resort

Leave early Friday and make the quick two-and-a-half-hour drive from Chicago, buzzing through Milwaukee before you reach Elkhart Lake and the 245-room Osthoff Resort (from $210). A booming summertime retreat for families that sits right on the spring-fed lake surrounded by cedars, the Osthoff still brings a scene in fall.

Go for the roomy one- to three-bedroom suites (ranging from 675 to 2,300 square feet), each of which includes a full kitchen, queen-size sleeper sofa, and a private balcony—plenty of room for you and your brood to spread out. The lakefront suite from $265 and overlooking pretty Elkhart is worth the splurge.

You’re here with the family, but if you can steal time for yourself, book a treatment at the 20,000-square-foot Aspira spa. Try the Hammam with a purifying salt scrub followed by a body shampoo and Moroccan hot oil massage ($240) and skip the messy Vichy shower treatments. (The onsite L’ecole de la Maison Cooking School is also excellent, but plan to sign up on your next visit, since most of the October classes are already booked.)

Hunt for Pumpkins at the Little Farmer

There are several great pumpkin farms within 20 miles of Elkhart Lake, but we love the true farm feel and patches that seem to go on forever at the Little Farmer Orchard and Farm Market. You won’t have to park miles away and you’ll find pumpkins of all shapes, sizes, and colors (the farm seeds 20 varieties across 20 acres), right by the farmhouse or out beyond the corn maze ($2.75). We recommend trekking to the patches with a little red wagon in tow (available first come, first serve), where you can pick a fresh pumpkin off the vine, then take the free tractor-pulled hay ride back to the farmhouse. Prices are reasonable, too, with six pumpkins running $23.

There’s always a long line for the sliced caramel apples, but head to the cozy coffee house instead for a slice of homemade apple pie and ice cream ($4.50) and to shop for seasonal crafts and Packer fan goods. If it’s warm, sit outside and sip your hot cocoa while the kids burn off steam around the play area.

Enjoy the Scenery at Lake Street Café

You could head back to the Osthoff for a fine dining experience at pretty Lola’s on the Lake (the Wisconsin cheese sampler is great). But Lake Street Café, just a block or two from the resort, is way more fun and unusual. The walls and shelves here are loaded with great Wisconsin kitsch, such as Schlitz signs, old license plates, and lots of colorful art—good material for family eye-spy games. Local craft brews are on tap and the eclectic menu shows up with out-of-the-box options for kids, homemade soups (try the lobster bisque), and dishes like duck sausage pizza with dried cherries and garlic. You can also bring your own wine with no corkage fee and free decanting.

Before You Go

Elkhart lake was formed by glaciers and is still considered one of the clearest lakes in Wisconsin. Make time to walk on the sandy beach or on trails around the lake and peer down to the lake’s bottom.

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