Area Transportation
- Lifestream has "The New Interurban" Van Service for local and regional public transportation.
Airports
- The Randolph County Airport is available for general aviation traffic.
- Dayton International Airport is about 70 minutes SE of Winchester.
- Indianapolis International Airport is about 90 minutes Southwest of the county.
Railroad
- Amtrack has a passenger terminal located in Connersville, Indiana with service to Indianapolis, Chicago, and to Cincinnati
- A CSX Freight line runs east and west through Randolph County
Highways & Roadways
- US 27, US 35, and US 36
- IN32, IN28, IN1, IN227
- 860 Miles of County roads
- 218 Bridges