Small Town Breakdown No. 32: Orleans, Indiana
In 2025 we are highlighting 52 small towns across the state of Indiana in 52 weeks. For our 32nd small town breakdown of the year, we’re going from Brookville in Franklin County to Orleans in Orange County. Orleans is 1 hour and 40 minutes south of Indianapolis, 55 minutes south of Bloomington, and 1 hour and 10 minutes northwest of Louisville.
What’s it like in Orleans?
Orleans is tucked away as a small town in southern Indiana, but it’ll grab your attention with a newly painted mural adorned on a trio of grain bins or when its many dogwoods are in bloom. The historic 1926 bandstand at Congress Square, and bites from Speakeasy Pizza or Dille’s Smoked Meats & Dillescious Treats are a few more reasons to stop the car when passing through.
The History of Orange County and Orleans, Indiana
Orange County was organized in 1816 from portions of Knox, Gibson and Washington counties. It was named after Orange County, North Carolina, from which early settlers came. Paoli is the county seat.
Prior to Orange County’s founding, Orleans was laid out in March 1815. It is the oldest platted town in the county and was named just two months after Andrew Jackson’s victory over the British at the Battle of New Orleans.
The New Albany-Salem Railroad came through town in the early 1850s, helping spark the local economy.
Orleans eventually became known as the “Dogwood Capital of Indiana” in 1970 when a mid-1960s initiative called “Operation Dogwood” helped beautify the town. Hundreds of dogwood trees were planted in the town square and along State Road 37 as drivers entered town.
As of the 2024 census Orleans’ population was 2,077, making it the second-largest of six incorporated towns/cities in Orange County behind Paoli (3,617). Orleans is tied with Edgewood for being the 223rd-largest city in Indiana.
Things to Do In or Near Orleans, Indiana
Every spring in late April, the annual Dogwood Festival is held. It first began in 1970 and includes carnival rides, arts, crafts, food vendors, live music, a car show, pageants, a parade, a best in show pet competition, and other festival happenings.
Check out Congress Square, the name of the town’s public square. It’s also referred to as “Seminary Square” in recognition of the Orleans Academy that stood in its place from 1864-1963. No matter how you refer to it, it’s home to a playground, restored 1926 brick bandstand or gazebo, shelter houses, and a fountain and sculpture in the center of the square.
While not yet entirely finished, the Monon South Trail is a newer attraction that opened its first 1 ¼-mile segment last December, navigating through downtown Orleans. It’s all part of a much larger 20-mile regional project that will draw locals and visitors who enjoy walking, running and biking, connecting Orleans to Mitchell.
If you like unique natural wonders, head to Lost River. Estimated to be 87 miles in length (nobody really knows because the caverns haven’t been fully explored), 23 miles of the Lost River actually flows underground and resurfaces at deep springs.
Places to Eat or Grab a Drink in Orleans, Indiana
Orleans may be small but hits above its weight on the culinary scene.
We’ll start at Dille’s Smoked Meats and Dillescious Treats. You’ll be hooked at first bite with the porky fries that are loaded with pulled pork, cheese, BBQ and green onions. They’ve also got a breaded tenderloin, sandwiches, subs, ribs, pies, and pizza locals love. We promise, you won’t leave with an empty stomach. Guests give ‘em 4.9 stars among over 40 Google reviews.
Next on the menu is Speakeasy Pizza, home to wood-fired pies and huge breadsticks deemed to be some of Indiana’s best. Pro tip: get the beer cheese sauce to go with them. You can thank us later. Speakeasy is located on the historic Congress Square in downtown and has racked up a 4.8-star Google rating with over 300 reviews.
If you’re looking to add a little spice to your taste buds, hop in to El Compadre for quesadillas, fajitas, pollo loco, guacamole and affordable prices. They’ve got 125 Google reviews and a 4.6-star rating. The Orleans location is one of six El Compadre restaurants in southern Indiana.
Orleans Jr/Sr High School State Championship
The Orleans Bulldogs and every other school in Orange County had never won an IHSAA team state championship… until March 29, 2025, when Orleans made school and county history by defeating Clinton Prairie 64-55 in the boys basketball 1A state championship game at Gainbridge Fieldhouse. The Bulldogs set 1A title game records by shooting 63.9 percent (23-of-36) from the field and 60 percent (6-of-10) behind the arc.
It had been over a century since Orleans had even reached the state tournament in boys basketball, doing so in three consecutive years from 1912-14. Its deepest run was a semifinal appearance in 1912, one year after the inaugural Running of the Indianapolis 500.
That’s it for small town breakdown No. 32 of 2025. Where should we head next?
