Scenic Midwest Road Trip Routes (With Itineraries!)

The Midwest is often called “America’s Heartland,” and for good reason. From rolling hills and lakefront views to charming small towns and wide-open farmland, there’s a surprising amount of beauty and diversity tucked into this region. If you’re looking to slow down, hit the open road, and discover places that aren’t overrun with tourists, these scenic Midwest road trip routes will inspire your next getaway.

Whether you’re chasing lake views, sipping local wine, or following historic highways, these curated itineraries offer the perfect balance of scenic beauty, great eats, and must-see stops.

1. Lake Michigan Circle Tour (Illinois, Indiana, Michigan, Wisconsin)

Length: 1,100+ miles

Duration: 5–7 days

One of the most iconic Midwest road trips, this loop around Lake Michigan offers everything: big cities, peaceful beach towns, sand dunes, lighthouses, and stunning lake views.

Itinerary Highlights:

• Chicago, IL: Start your trip with deep-dish pizza, Millennium Park, and lakefront views.

• Indiana Dunes National Park: Climb sand dunes or relax on the beach just outside Chicago.

• New Buffalo, MI: Wine tastings and cozy beaches in Michigan’s harbor country.

• Holland, MI: A charming Dutch-inspired town with tulips in spring and a beach vibe in summer.

• Traverse City, MI: The gateway to Sleeping Bear Dunes, cherry orchards, and local wineries.

• Mackinac Island: A ferry ride here is a must—no cars, just bikes and horse-drawn carriages.

• Green Bay, WI: Stop by Lambeau Field or explore Door County’s lighthouses and lake towns.

• Milwaukee, WI: Beer, bratwurst, and lakefront culture before heading back to Chicago.

Door County’s Lighthouse

2. Route 66: Midwest Edition (Illinois to Missouri)

Length: ~300 miles

Duration: 2–4 days

Get your kicks on the classic Route 66—starting in Chicago and stretching through small towns to the Missouri border. This shorter section is packed with nostalgic Americana, quirky roadside stops, and iconic eats.

Itinerary Highlights:

• Chicago, IL: Start at the official Route 66 sign downtown and grab breakfast at Lou Mitchell’s.

• Pontiac, IL: Home to the Route 66 Hall of Fame and vibrant wall murals.

• Springfield, IL: Visit the Lincoln Home National Historic Site and try a “horseshoe” sandwich.

• Litchfield, IL: Retro diner vibes and a charming town square.

• Cuba, MO: Known as “Mural City,” it’s a great artsy stop before reaching…

• St. Louis, MO: End your route at the Gateway Arch and indulge in some St. Louis-style BBQ or gooey butter cake.

Gateway Arch

3. Missouri Wine Country (Hermann to Augusta)

Length: ~150 miles

Duration: 2–3 days

This underrated wine region offers rolling hills, charming German towns, and dozens of scenic vineyards along the Missouri River. Perfect for couples, girlfriends’ getaways, or a relaxing long weekend.

Itinerary Highlights:

• Hermann, MO: A German-style village with historic buildings, live music, and local wines. Don’t miss Hermannhof or Stone Hill Winery.

• Missouri River Valley Scenic Drive: Take Highway 94 (nicknamed the “Missouri Weinstrasse”) and enjoy winding drives through vineyards and farmland.

• Augusta, MO: A quaint wine town with top wineries like Montelle and Mount Pleasant, plus a lovely state park nearby for a post-wine hike.

• Defiance & St. Charles, MO: More wineries, historic streets, and local dining options. Bonus: St. Charles has a walkable riverfront downtown.

Missouri River Valley Scenic Drive

Road Trip Tips for Midwest Adventures:

• Best Time to Go: Late spring to early fall offers the best weather, especially for lake views, winery visits, and small-town festivals.

• Pack Layers: Midwest weather can be unpredictable—even in summer.

• Support Local: Visit local diners, boutiques, and family-run wineries to get the most authentic experience.

• Stay Flexible: Some of the best moments happen when you take a detour or stumble into a festival you didn’t know was happening.

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The Midwest is full of road trip-worthy treasures if you know where to look. From coastal-feeling lake loops to wine-filled weekends and classic highways that whisper stories of the past, there’s something here for every kind of traveler. So gas up, cue the playlist, and let the road lead you to the heart of America.