How far is Winchester, IN from Bloomington, IN?
The driving distance from Winchester, IN to Bloomington, IN is about 139 miles (223.7 km), with a travel time of about 02h 38m by car.
- The straight-line flight distance is about 107.7 miles (173.3 km).
- For a round trip, plan for roughly 05h 17m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
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 02h 38m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
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.
City in Indiana, United States; county seat of Hancock County
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Sunny
Driving Route Map
The map below follows the saved road route between Winchester and Bloomington.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winchester and Bloomington.
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1
Start on South Main Street
62 m · 6 sec · South Main Street
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2
Turn right onto East Washington Street
1469 ft · 42 sec · East Washington Street
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3
Turn right onto Southeast Greenville Avenue
1105 ft · 19 sec · Southeast Greenville Avenue
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4
Continue on East Greenville Avenue
2426 ft · 43 sec · East Greenville Avenue
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5
Turn right
21.1 mi · 24 min
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6
Take the exit slight right
1526 ft · 37 sec
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7
Merge slight left
60.8 mi · 1 hr 10 min
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8
Take the exit slight right toward I 465 South, I 465 North
1463 ft · 26 sec
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9
Keep slight left to continue on I 465 South
1 mi · 2 min
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10
Merge slight left
4.4 mi · 5 min
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11
Continue straight
8.7 mi · 10 min
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12
Keep slight right to continue on I 69 South: Evansville
39.3 mi · 44 min
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13
Take the exit slight right toward College Avenue, Walnut Street
2423 ft · 59 sec
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14
Turn straight onto North Walnut Street
3.2 mi · 5 min · North Walnut Street
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15
Continue on North College Avenue
2714 ft · 53 sec · North College Avenue
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16
Turn left onto West 17th Street
2175 ft · 49 sec · West 17th Street
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17
Turn right onto North Indiana Avenue
2676 ft · 1 min · North Indiana Avenue
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18
Turn right onto East 10th Street
114 m · 16 sec · East 10th Street
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19
Turn left onto North Dunn Street
2227 ft · 1 min · North Dunn Street
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20
Turn left onto East 4th Street
115 m · 13 sec · East 4th Street
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21
Turn straight
30 m · 7 sec
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22
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Winchester and Bloomington.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
East Greenville Avenue
Merge slight left
60.8 mi · 01h 10m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Mostly Sunny leaving Winchester and Sunny near Bloomington.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winchester to Bloomington?
The road trip is about 139 miles (223.7 km) and usually takes 02h 38m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Greenfield is a useful midpoint, sitting about 71.3 miles from Winchester and 67.7 miles from Bloomington.
How much longer is the road route than the straight-line distance?
The direct path is about 107.7 miles (173.3 km), while the road route adds roughly 31.3 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 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 1:12 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $18.52 one way or $37.03 round trip. Estimated CO2 is about 43.6 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Winchester and Sunny near Bloomington.
Stop Ideas Near Greenfield
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 Greenfield.
Indianapolis Union Station
Connersville station
Crawfordsville
Crawfordsville (Bus), Indiana
Flight Path Map
This map shows the direct air route between Winchester and Bloomington. Straight-line distance: 107.65 mi (173.25 km).
#1 Winchester
City in White River Township, Randolph County, Indiana, United States
| Population | 4,566 |
| Coordinates | 40.1719900, -84.9813500 |
| Altitude | 333 |
| Country | United States |
#2 Bloomington
The most populous city in Monroe County, Indiana.
| Population | 85,603 |
| Coordinates | 39.1653300, -86.5263900 |
| Altitude | 235 |
| Country | United States |
End: South Indiana Avenue (-86.52691, 39.165322)
Estimated Travel Time
Distance: 224 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 04h 37m |
| 40 mph (64.37 km/h) | 03h 28m |
| 50 mph (80.47 km/h) | 02h 46m |
| 60 mph (96.56 km/h) | 02h 18m |
| 70 mph (112.65 km/h) | 01h 59m |
| 80 mph (129 km/h) | 01h 44m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $18.52 | $37.03 |
| Mid-grade | $4.25 | $20.88 | $41.76 |
| Premium | $4.65 | $22.85 | $45.70 |
| Diesel | $5.30 | $26.04 | $52.09 |
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 Indiana · May 13, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.