North America Travel Tips

Midwestern Road Trips – Best Midwest Cities to Visit

midwestern road trips image hanging out the car window

Welcome to the heartland of the USA, the Midwest! – Explore the best cities on our guide to Midwestern road trips. Journey with us through the expansive landscapes, historic towns, and thriving cities that define the essence of the Midwest. From the picturesque shores of the Great Lakes to the rolling plains of the prairie, explore the top Midwest destination by each state within the iconic Midwest!

Our complete guide to the best Midwest cities to visit invites you to explore the diverse and captivating destinations that make the Midwest a road-tripper’s dream. Get ready to hit the open road and uncover the hidden gems, cultural treasures, and natural wonders that await along your Midwestern adventure!

Midwestern Road Trips – Michigan

Traverse City, Michigan:

A Midwest destination that captivates visitors with its charming downtown streets with abundant shopping options, outdoor recreation options, cultural richness, and culinary delights. Top activities in Traverse City, Michigan:

  1. Charming Waterfront: Nestled along the shores of Lake Michigan’s Grand Traverse Bay, Traverse City offers stunning waterfront views. The bay’s crystal-clear waters provide a picturesque backdrop for outdoor activities and relaxation.
  2. Wine Country & Craft Beer: Traverse City is at the heart of Michigan’s wine country, particularly known for its vineyards and wineries along the Old Mission and Leelanau Peninsulas. Wine and craft beer enthusiasts can indulge in tastings of locally-produced wines and freshly brewed craft beers, featuring both traditional and unique varietals. Book a tour of 4 local wineries (tasting included!) here!
  3. Explore our guide on Traverse City, “Things to do in Traverse City”, for a complete list of top stops and must-see’s in this stunning city
A craft beer flight in the Midwest city traverse city, Michigan.

Grand Haven, Michigan:

Grand Haven is a charming waterfront town on the eastern shore of Lake Michigan that offers a delightful mix of natural beauty, outdoor activities, and a welcoming community. The vast beaches and iconic pier and boardwalk offer a view of Lake Michigan that is second to none! Top activities in Grand Haven:

  • Outdoor Recreation: The town is a haven for outdoor enthusiasts. In addition to the beaches, Grand Haven offers opportunities for hiking, biking, fishing, and water sports. The nearby dunes and parks provide scenic landscapes for exploration.
  • Downtown Shopping and Dining: The downtown area of Grand Haven is charming, with boutique shops, art galleries, and a variety of restaurants. Visitors can explore the streets, enjoy local cuisine, and appreciate the friendly atmosphere.
  • Boardwalk and Waterfront Stadium: The Grand Haven Boardwalk provides a scenic route along the Grand River, offering views of boats and marinas. The Waterfront Stadium hosts events and concerts, providing a lively atmosphere along the waterfront.
  • Bonus Tip: Grand Haven is just a short drive from Holland, Michigan: Be sure to add this charming town on your Midwestern road trips itinerary for its wide variety of shopping, food options, and outdoor recreation! Be sure to read up on Holland, Michigan and everything it has to offer on our complete guide, “Best Budget-Friendly Travel Tips Holland, MI”
A picture of the Grand Haven pier.

Midwestern Road Trips – Ohio

Cleveland, Ohio

Cleveland, Ohio, is a vibrant city with a rich cultural heritage, diverse attractions, and a thriving arts scene. For Midwestern road trips, explore Cleveland’s extremely vibrant nightlife scene, try your luck at a casino, or explore the Rock N Roll Hall of Fame in this iconic city! Top Activities in Cleveland, Ohio:

  • Rock and Roll Hall of Fame: Cleveland is home to the iconic Rock and Roll Hall of Fame, a must-visit for music enthusiasts. The museum showcases the history of rock and roll through exhibits, artifacts, and interactive displays dedicated to legendary artists.
  • West Side Market: One of the oldest public markets in the country, the West Side Market offers a diverse array of fresh produce, meats, and international foods. It’s a great place to explore and sample local flavors.
  • Nightlife Scene & Cleveland Arcade: Be sure to read up on the highlights of Cleveland’s iconic nightlife scene and the Cleveland Arcade on our complete guide, “24 Hours in Cleveland Ohio: Things to Do This Weekend in Cleveland“!
cleveland arcade this weekend
explore 4th street in cleveland this weekend

Midwestern Road Trips – Wisconsin

Milwaukee, Wisconsin

Milwaukee is a top destination for Midwestern road trips for its rich brewing heritage! With brewery tours and craft beer experiences galore, Milwaukee is a beer lovers dream. Explore cultural institutions like the Milwaukee Art Museum and Harley-Davidson Museum. Enjoy the scenic Lake Michigan waterfront, Riverwalk, and parks. Experience the diverse neighborhoods, from the historic Third Ward to trendy Brady Street! Top Activities in Milwaukee, Wisconsin:

  • Brew City Heritage: Milwaukee has a strong brewing tradition, earning it the nickname “Brew City.” Visitors can explore the historic Pabst Mansion, tour the Miller Brewing Company, and sample craft beers at the numerous breweries and beer gardens throughout the city. Book a tour of the various breweries here!
  • Harley-Davidson Museum: Motorcycle enthusiasts should not miss the Harley-Davidson Museum, which showcases the iconic brand’s history and culture. The museum features a vast collection of motorcycles, memorabilia, and interactive exhibits.
  • Lake Michigan and Riverwalk: Milwaukee’s waterfront is defined by the shores of Lake Michigan and the Milwaukee River. The Riverwalk offers scenic strolls, waterfront dining, and access to attractions like the Milwaukee Art Museum and Discovery World.
  • Diverse Neighborhoods: Milwaukee’s neighborhoods each have their own character and charm. From the historic Third Ward with its art galleries and boutiques to the trendy Brady Street and the laid-back atmosphere of Bay View, there’s something for every taste.

Midwestern Road Trips: Illinois

Chicago, Illinois

Add the Windy City on your Midwest road trips itinerary for its iconic skyline, world-class architecture, and Millennium Park’s attractions. Experience vibrant cultural scenes with renowned museums, theaters, and music venues. The bustling city offers diverse culinary delights, from deep-dish pizza to international cuisine. Chicago has a stunning view of Lake Michigan’s waterfront, offers arcade games and rides on Navy Pier, and scenic riverwalks. Be sure to explore unique neighborhoods like the Loop, Magnificent Mile, and Wicker Park! Top Activities in Chicago, Illinois:

  • Millennium Park: Explore Millennium Park, home to the famous Cloud Gate sculpture (affectionately known as “The Bean”), Crown Fountain, and Jay Pritzker Pavilion. It’s a central hub for art, music, and outdoor enjoyment.
  • Navy Pier: Enjoy panoramic views of Lake Michigan, ride the Ferris wheel, and explore entertainment options at Navy Pier. The pier offers dining, shopping, and various attractions for visitors of all ages.
  • Magnificent Mile: Shop along the Magnificent Mile, a renowned shopping district on Michigan Avenue featuring luxury boutiques, department stores, and a variety of dining options.
  • Chicago Riverwalk: Stroll along the Chicago Riverwalk, a scenic pathway lined with cafes, parks, and public art. It offers a relaxing way to experience the city’s architecture and urban ambiance.
a view of midwest chicago streets
a picture of the bean in chicago illinois!

Midwestern Road Trips: Indiana

Indianapolis, Indiana

Indianapolis, the capital city of Indiana, offers a diverse range of attractions for your midwestern road trip! Known for its rich sports culture, visitors can explore the iconic Indianapolis Motor Speedway, home of the famous Indianapolis 500. The city also boasts a vibrant arts scene, with the Indianapolis Museum of Art and the Kurt Vonnegut Museum. Additionally, downtown Indianapolis offers a lively culinary scene, a variety of shops, and cultural events. Top Activities in Indianapolis, Indiana:

  • Indianapolis Motor Speedway: Visit the iconic Indianapolis Motor Speedway, home to the Indianapolis 500. Take a tour of the track, explore the museum, and immerse yourself in the history of auto racing.
  • Downtown Indianapolis: Wander through downtown to experience the city’s vibrant atmosphere. Explore Monument Circle, surrounded by shops, restaurants, and cultural institutions. Don’t miss the Soldiers and Sailors Monument.
  • Indianapolis City Market: Explore the historic Indianapolis City Market, offering a variety of local vendors, restaurants, and unique shops.
An image of the bustling streets in downtown Indianapolis indiana.

Turkey Run State Park, Indiana

Looking for something less urban for your Midwest road trip destination? Turkey Run State Park, located in Parke County, Indiana, is a scenic and popular destination known for its rugged beauty and outdoor recreation opportunities. The park features deep sandstone gorges formed by Sugar Creek, offering stunning landscapes and challenging hiking trails. Visitors can explore the iconic Suspension Bridge, traverse ladders and rugged trails at the Punch Bowl, and enjoy picturesque views from locations like Lover’s Leap.

An image of the natural gorge in Turkey Run state park in the midwest.
A natural waterfall in turkey run state park.

Midwestern Road Trips: Kentucky

Louisville, Kentucky

As a destination on our Midwest road trip destinations, Louisville is an absolute must-stop with its unique blend of Southern charm, rich cultural heritage, and diverse attractions. From the world-famous Kentucky Derby and Bourbon Trail to the Muhammad Ali Center, charming neighborhoods like Old Louisville, and a thriving culinary scene, the city offers a vibrant tapestry of experiences that cater to history enthusiasts, sports fans, bourbon aficionados, and those seeking a taste of genuine Southern hospitality. Top Activities in Louisville, Kentucky:

  • Bourbon Distilleries: Louisville is part of the Kentucky Bourbon Trail, and there are several distilleries in the area, including the Evan Williams Bourbon Experience and the Bulleit Frontier Whiskey Experience, where visitors can learn about the bourbon-making process.
  • Waterfront Park: The city boasts a beautiful Waterfront Park along the Ohio River, providing green spaces, walking paths, and recreational activities. The Big Four Bridge, connecting Louisville to Jeffersonville, Indiana, is a popular spot for walking and biking.
  • Culinary Scene: Louisville has a thriving culinary scene, with a focus on Southern comfort food, bourbon-infused dishes, and innovative dining experiences. Try the Hot Brown, a local culinary specialty.
  • Louisville Mega Cavern: Adventure seekers can experience an underground zip line and aerial ropes challenge course in the Louisville Mega Cavern, an enormous man-made cavern.
A bar in Louisville Kentucky showcasing the bourbon they sell.

Midwestern Road Trips: Minnesota

Duluth, Minnesota

Duluth, nestled on the western tip of Lake Superior in Minnesota, is a captivating Midwest destination known for its natural beauty and outdoor adventures. Explore Duluth’s waterfront views on the Aerial Bridge. Visitors can explore pristine forests, hike along the Superior Hiking Trail, and witness breathtaking waterfalls. Top Activities in Duluth, Minnesota:

  • Scenic Beauty: Duluth, located on the shores of Lake Superior, offers stunning scenic beauty with its lakeside landscapes, parks, and the iconic Aerial Lift Bridge.
  • Outdoor Activities: The city is a gateway to outdoor adventures, including hiking, biking, and water activities. The nearby North Shore is known for its picturesque waterfalls and hiking trails.
  • Lake Superior Maritime Visitor Center: Learn about the maritime history of the region and watch ships navigate the harbor at this informative visitor center.

Midwestern Road Trips: North Dakota

Valley City, North Dakota

Valley City, situated along the scenic Sheyenne River in North Dakota, invites visitors to experience its blend of natural beauty and small-town charm. Known for the Sheyenne River Valley Scenic Byway, the city offers breathtaking drives through rolling hills and opportunities for outdoor activities at places like Baldhill Dam and Recreation Area. Explore the charming downtown filled with shopping and restaurant options! Top Activities in Valley City, North Dakota:

  • Sheyenne River Valley Scenic Byway: Valley City is a gateway to the picturesque Sheyenne River Valley Scenic Byway, providing scenic drives through rolling hills, charming towns, and the serene beauty of the Sheyenne River.
  • Charming Downtown: The downtown area boasts historic architecture, local shops, and dining options. The city’s Main Street is recognized for its friendly atmosphere and community spirit.
  • North Country National Scenic Trail: Outdoor enthusiasts can explore sections of the North Country National Scenic Trail, which passes through Valley City, offering hiking opportunities amidst the region’s natural landscapes.
a view from Sheyenne River Valley Scenic Byway in north dakota.

Midwestern Road Trips: South Dakota

Black Hills, South Dakota

Home to the iconic Mount Rushmore, Black Hills is an iconic Midwest road trip destination! Mount Rushmore, where the faces of four U.S. presidents are carved into granite cliffs, is just one of the aspects of Black Hills that offers a rich blend of history and natural wonders. Custer State Park provides an opportunity for wildlife viewing, and the scenic Needles Highway winds through unique rock formations. Top Activities in Black Hills, South Dakota:

  • Mount Rushmore National Memorial: Witness the iconic Mount Rushmore, where the faces of Presidents Washington, Jefferson, Roosevelt, and Lincoln are carved into the granite cliffs. The nightly lighting ceremony is a must-see. Book a bus tour of Mount Rushmore here!
  • Deadwood: Immerse yourself in the Wild West history of Deadwood, known for its historic Main Street, casinos, and events. Visit Mount Moriah Cemetery, where Wild Bill Hickok and Calamity Jane are buried.
  • Spearfish Canyon: Drive through Spearfish Canyon, known for its lush scenery, waterfalls, and hiking trails. Bridal Veil Falls and Roughlock Falls are popular stops.
a picture of the iconic mount rushmore in black hills south dakota.

In conclusion, embarking on a road trip through the Midwestern United States promises a journey filled with diverse landscapes, rich cultural experiences, and a tapestry of unique destinations. From the vibrant cityscape of Chicago to the serene beauty of the Great Lakes, the historical charm of towns like Indianapolis, Indiana, and the iconic landmarks of the Black Hills in South Dakota, the Midwest offers a dynamic blend of urban excitement and natural wonders. Whether exploring the shores of Lake Michigan, traversing scenic highways, or immersing oneself in the heartland’s cultural heritage, a Midwestern road trip unveils the region’s hidden gems and invites travelers to discover the often overlooked but captivating beauty of America’s heartland! Happy Traveling!

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