How far is Bloomington, IN from Winchester, IN?
The driving distance from Bloomington, IN to Winchester, IN is about 142.3 miles (229 km), with a travel time of about 02h 46m by car.
- The straight-line flight distance is about 107.7 miles (173.3 km).
- For a round trip, plan for roughly 05h 33m 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 46m.
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.
Sunny
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Bloomington and Winchester.
Turn-by-Turn Driving Directions
Step-by-step road directions between Bloomington and Winchester.
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1
Start on the route
30 m · 11 sec
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2
Turn right onto South Indiana Avenue
1083 ft · 39 sec · South Indiana Avenue
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3
Turn left onto East 7th Street
1881 ft · 1 min · East 7th Street
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4
Turn right onto North Walnut Street
4.4 mi · 7 min · North Walnut Street
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5
Take the ramp straight
1834 ft · 45 sec
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6
Merge slight left
47.8 mi · 54 min
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7
Continue straight
4.9 mi · 6 min
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8
Take the exit slight right toward I 70 East: Dayton
1.3 km · 2 min
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9
Merge slight left onto Dwight D Eisenhower Highway
60.8 mi · 1 hr 10 min · Dwight D Eisenhower Highway
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10
Take the exit slight right toward US 27: Chester Boulevard
1825 ft · 31 sec
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11
Keep slight left to continue on US 27: Chester Boulevard
124 m · 11 sec
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12
Merge slight right onto Chester Boulevard
5.4 mi · 6 min · Chester Boulevard
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13
Continue on Chester Blvd
1.2 km · 53 sec · Chester Blvd
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14
Continue on Cross Street
6 mi · 7 min · Cross Street
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15
Continue on South Main Street
9.1 mi · 10 min · South Main Street
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16
Turn left onto East Greenville Avenue
2426 ft · 41 sec · East Greenville Avenue
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17
Continue on Southeast Greenville Avenue
1105 ft · 20 sec · Southeast Greenville Avenue
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18
Turn left onto East Washington Street
1469 ft · 47 sec · East Washington Street
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19
Turn left onto South Main Street
62 m · 4 sec · South Main Street
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20
Arrive at your destination
0 m · 1 sec · South Main Street
Car Route Details
A richer read on the saved driving route between Bloomington and Winchester.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
Dwight D Eisenhower Highway
Merge slight left onto Dwight D Eisenhower Highway
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.
Sunny leaving Bloomington and Mostly Sunny near Winchester.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Bloomington to Winchester?
The road trip is about 142.3 miles (229 km) and usually takes 02h 46m 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 71.1 miles from Bloomington and 71.2 miles from Winchester.
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 34.6 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 12:56 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $18.93 one way or $37.86 round trip. Estimated CO2 is about 44.6 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Bloomington and Mostly Sunny near Winchester.
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 Bloomington and Winchester. Straight-line distance: 107.65 mi (173.25 km).
#1 Bloomington
The most populous city in Monroe County, Indiana.
| Population | 85,603 |
| Coordinates | 39.1653300, -86.5263900 |
| Altitude | 235 |
| Country | United States |
#2 Winchester
City in White River Township, Randolph County, Indiana, United States
| Population | 4,566 |
| Coordinates | 40.1719900, -84.9813500 |
| Altitude | 333 |
| Country | United States |
End: Winchester (-84.98135, 40.17199)
Estimated Travel Time
Distance: 229 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 04h 44m |
| 40 mph (64.37 km/h) | 03h 33m |
| 50 mph (80.47 km/h) | 02h 50m |
| 60 mph (96.56 km/h) | 02h 22m |
| 70 mph (112.65 km/h) | 02h 01m |
| 80 mph (129 km/h) | 01h 46m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $18.93 | $37.86 |
| Mid-grade | $4.25 | $21.35 | $42.70 |
| Premium | $4.65 | $23.36 | $46.73 |
| Diesel | $5.30 | $26.63 | $53.25 |
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.