Southern Indiana is a vast region with rolling hills and countless stories. We’re getting ready to go on a road trip along US 150 and are putting together a list of the best eats, sleeps, and stops. Join us on our journey as we start along the famous Wabash River on the Indiana-Illinois border in Vincennes, Indiana.
On the southwest side of Indiana between Evansville and Terre Haute, you’ll find Indiana’s oldest settlements. Vincennes used to be the capital of the Indiana Territory. It was settled by French fur traders in the 1700s, and quickly became a bustling trading post and fort. Farms started popping up all over the countryside. Although Vincennes has transformed throughout the centuries, the French influence and farming culture is something locals are still proud of.
Driving through the Knox County countryside, farms, U-picks, and farmers markets are unavoidable. While strawberries, peaches, and corn are staples, the area is known for its amazing watermelon. It’s truly the best watermelon we’ve ever eaten.
As you walk around Vincennes, you’ll notice the French flair. Fleur de lis decorates buildings and walkways. Some street names nod to the city’s French roots. Enjoy the laid-back historic town in all its quaint glory.

What to Eat
Breakfast:
Dot’s Custom Cakes & Catering is a homestyle café in a historic downtown area, making it easy to grab a bite and go explore. You can expect all the favorites, but we’d recommend the French toast.
Lunch:
Pea-Fections has been serving up soups, sandwiches, and salads for over 20 years. Everything on the menu is amazing, but the cheesecakes and tortes are heavenly!
Dinner:
The basil pasta and Greek salad from Procopio’s Pizza & Pasta is to die for! The fresh, authentic flavors, and relaxed, Italian atmosphere makes it Vincennes’ go-to date night spot.
Where to Go
Best of the Best:
Indiana Military Museum features the Midwest’s most extensive collection and displays of vintage vehicles, weaponry, uniforms, and artifacts. You’ll get to explore the life and times of the brave U.S. military men and women from the Civil War to present day.
Uniquely Southern Indiana:
The hilarious entertainer, Red Skelton, was born and raised in Vincennes, Indiana. He brought beloved characters on the small screens to life during the Golden Age of Television. Red Skelton Museum of American Comedy celebrates his life and legacy with good ol’ fashion laughs and interactive exhibits.
Local Gem:
Locals flock to George Rogers Clark National Historical Park for more than its gorgeous monument. The massive granite memorial and stunning flowering trees are the perfect backdrop for a weekend festival or picnic.
Where to Sleep
Affordable Accommodations:
Be one with nature in rustic and charming in the cabins at Ouabache Trails Park. Each cabin is furnished with a TV, full kitchen, air conditioning, heating, and plumbing. You’ll need to bring your own linens and toiletries.
Better Boarding:
The cute and cozy Reily Home Bed & Breakfast is a restored historic home with private bathrooms and comfy bedrooms. The quiet residential area is close to many of Vincennes attractions and dining.
Luxury Lodging:
Vincennes’ newest hotel, Hampton Inn, offers sleek and upscale rooms in the heart of the city. Hot breakfast is served every morning with fresh waffles and oatmeal. Guests on the go will also enjoy a complimentary breakfast bag.
There are many great times of year to visit and the best is festival time. Downtown becomes lively during First Friday art walks with food, wine, beer, entertainment, and, of course, art. Living history events, such as Muster on the Wabash and Spirit of Vincennes Rendezvous, give you a chance to see history in the making. No matter what you do or where you go in Vincennes, you’ll enjoy laid-back Hoosier Hospitality.
On our next stop along US 50, we will find ourselves enjoying the Amish way of life in Daviess County.