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In Oshkosh, Wisconsin, the hardest part is choosing what to do first — sample both famous chocolate shops, pull up to drive-in restaurants, explore the EAA Museum, catch a Wisconsin Herd basketball game or cruise the Fox River on a tiki bar boat. The city is full of great options!

Pleasant Prairie and Mount Pleasant in southeastern Wisconsin are aptly named. Discover a cheese castle, local farms, kringle, scenic nature and the world’s sixth-best pizza. Add stops like Bristol Renaissance Faire and Apple Holler, and you’ll have plenty of reasons to get off I-94.

Crown Point, Indiana has a lot to teach. John discovers corn ice cream, gemstones, creative art spaces and that spending time in jail can be ... fun. Emmy learns she enjoys mead, that renovation differs from restoration, and that even a courthouse can be entertaining. Learning is part of the fun in Crown Point!

St. Joseph and Benton Harbor, Michigan share a close sister-city bond. St. Joseph charms with a pristine beach and a quaint main street of local shops. Benton Harbor brings a scrappy, creative spirit, with vibrant arts and great food. Together, they offer the whole package!

Stevens Point, Wisconsin is home to familiar favorites like Stevens Point Brewery, the Green Circle Trail, SentryWorld and Father Fats. But there’s more to discover, including Main Grain Bakery, the Food + Farm Exploration Center, Gamber Johnson, Schmeeckle Reserve at UW–Stevens Point and the Hostel Shoppe.

Greendale, Wisconsin is a place that draws you in, whether you’re just visiting or putting down roots. Built as a planned suburb of Milwaukee by the WPA during the Great Depression, Greendale’s walkable streets and storybook charm feel like a Norman Rockwell painting brought to life. True to the city's slogan, “You just gotta see Greendale!”

Wisconsin really does have a West Coast, and it’s idyllic. Along Lake Pepin on the Mississippi River, five Wisconsin towns — Nelson, Pepin, Stockholm, Maiden Rock and Bay City — line the Great River Road. Agritourism and weddings draw visitors, but it’s the scenery and the pie that steal the show!

Lanesboro, Minnesota, lies in scenic bluff country and lives up to its reputation as one of the Midwest’s most charming towns. It’s known for top-notch trout fishing, a thriving Amish community, live theater, great food and inviting places to stay. It’s also home to a livestock Sales Commission — the first John and Emmy have ever experienced!

Elmhurst, Illinois, was built for its proximity to downtown Chicago, but it's far more than a bedroom community. With deep local history and a unique character, this suburb stands on its own merits — and on weekends, a free trolley makes exploring it even easier!

Eagle River, Wisconsin, holds on to its "Up North" roots of supper clubs, bars, shops, fishing, snowmobiling and hockey, while embracing a surge of new energy. Community gathering spots, diverse dining and a growing nightlife make this a destination worth a closer look.

Walker's Point sits at the transition between downtown Milwaukee and the south side. For nearly two centuries, people have lived, worked and gathered here. Once home to German and Polish immigrants, the neighborhood today has a strong Latino identity and a lively, ever-evolving character.

Ames, Iowa, sits amid vast cornfields, and Iowa State University gives it outsized heft and ambition. Beyond engineering, sports and public art, the campus is home to the impressive Reiman Gardens. And the compact, walkable downtown Ames is one of the most charming in the Midwest.

Port Washington, Wisconsin, sits on Lake Michigan, but has the easy charm of a New England seaside town. Charter fishing boats line the marina, pulling in salmon and more. A block west, downtown is the definition of Main Street, USA — friendly and postcard perfect! Port Washington, thank you for the perfect wrap for this season of Main Streets!