How far is Simpsonville, KY from Jacksonville, KY?
The driving distance from Simpsonville, KY to Jacksonville, KY is about 22.1 miles (35.5 km), with a travel time of about 00h 36m by car.
- The straight-line flight distance is about 18.9 miles (30.4 km).
- For a round trip, plan for roughly 01h 13m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 7:00 AM to 7:00 PM EDT.
Reverse, save, or send this route
This is an easy same-day return drive. Copy the route link, send it to another device, or print a clean version before you head out.
This is an easy same-day return drive.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 00h 36m.
This is a short drive, so your comfort window is wide. Traffic and current weather matter more than the clock.
You are leaving earlier than the recommended window, which gives you extra margin for breaks and traffic.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Township in Shelby County, Illinois
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Clear
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Simpsonville and Jacksonville.
Turn-by-Turn Driving Directions
Step-by-step road directions between Simpsonville and Jacksonville.
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1
Start on 3rd Street
20 m · 9 sec · 3rd Street
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2
Turn left onto Shelbyville Road
5.3 mi · 8 min · Shelbyville Road
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3
Continue on Midland Trail
1.4 mi · 2 min · Midland Trail
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4
Continue on Main Street
1.6 mi · 2 min · Main Street
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5
Continue on Frankfort Road
580 ft · 18 sec · Frankfort Road
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6
Turn left onto Boone Station Road
1.2 mi · 2 min · Boone Station Road
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7
Turn right onto Cropper Road
4.4 mi · 8 min · Cropper Road
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8
Continue on Bagdad Road
4.8 mi · 9 min · Bagdad Road
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9
At the end of the road, turn left onto Elmburg Road
610 ft · 12 sec · Elmburg Road
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10
Turn straight onto Bagdad Road
1.4 km · 2 min · Bagdad Road
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11
Continue on Bagdad Road
2.3 mi · 4 min · Bagdad Road
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12
Arrive at your destination
0 m · 1 sec · Bagdad Road
Car Route Details
A richer read on the saved driving route between Simpsonville and Jacksonville.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
Shelbyville Road
Turn left onto Shelbyville Road
5.27 mi · 00h 08m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A short regional drive
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
Mostly Clear leaving Simpsonville and Mostly Sunny near Jacksonville.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Simpsonville to Jacksonville?
The road trip is about 22.1 miles (35.5 km) and usually takes 00h 36m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
What is the halfway point on this route?
Shelbyville is a useful midpoint, sitting about 11 miles from Simpsonville and 11.1 miles from Jacksonville.
How much longer is the road route than the straight-line distance?
The direct path is about 18.9 miles (30.4 km), while the road route adds roughly 3.2 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 7:00 AM to 7:00 PM EDT. If you want a more comfortable same-day return, try to leave by 7:16 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $2.94 one way or $5.88 round trip. Estimated CO2 is about 6.9 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Clear around Simpsonville and Mostly Sunny near Jacksonville.
Stop Ideas Near Shelbyville
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Shelbyville.
Louisville, Kentucky
Cincinnati Museum Center at Union Terminal
Cincinnati, OH
Flight Path Map
This map shows the direct air route between Simpsonville and Jacksonville. Straight-line distance: 18.91 mi (30.43 km).
#1 Simpsonville
Human settlement in Shelby County, Kentucky, United States of America
| Population | 2,963 |
| Coordinates | 38.2225700, -85.3552300 |
| Altitude | 243 |
| Country | United States |
#2 Jacksonville
Jacksonville is a place in Kentucky, United States.
| Population | 0 |
| Coordinates | 38.2742400, -85.0130100 |
| Altitude | 275 |
| Country | United States |
End: Jacksonville (-85.01301, 38.27424)
Estimated Travel Time
Distance: 35 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 00h 44m |
| 40 mph (64.37 km/h) | 00h 33m |
| 50 mph (80.47 km/h) | 00h 26m |
| 60 mph (96.56 km/h) | 00h 22m |
| 70 mph (112.65 km/h) | 00h 18m |
| 80 mph (129 km/h) | 00h 16m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $2.94 | $5.88 |
| Mid-grade | $4.25 | $3.32 | $6.63 |
| Premium | $4.65 | $3.63 | $7.26 |
| Diesel | $5.30 | $4.14 | $8.27 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in Kentucky · Apr 18, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.