How far is Olive Branch, MS from Winona, MS?
The driving distance from Olive Branch, MS to Winona, MS is about 115.8 miles (186.3 km), with a travel time of about 02h 12m by car.
- The straight-line flight distance is about 102.4 miles (164.8 km).
- For a round trip, plan for roughly 04h 25m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM CDT.
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 12m.
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.
Human settlement in Panola County, Mississippi, United States of America
Route Weather Snapshot
Check the forecast at both ends before you head out.
Sunny
Driving Route Map
The map below follows the saved road route between Olive Branch and Winona.
Turn-by-Turn Driving Directions
Step-by-step road directions between Olive Branch and Winona.
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1
Start on Goodman Road
79 m · 13 sec · Goodman Road
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2
Turn left onto Cockrum Road
6.2 mi · 11 min · Cockrum Road
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3
Take the ramp right toward Tunica
1702 ft · 42 sec
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4
Merge slight left
9.2 mi · 10 min
-
5
Take the exit slight right toward I 55 South: Jackson
1833 ft · 45 sec
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6
Keep slight left to continue on I 55 South: Jackson
1.2 km · 2 min
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7
Merge slight left
96 mi · 1 hr 43 min
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8
Take the exit slight right
1228 ft · 30 sec
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9
Keep slight left
98 m · 8 sec
-
10
Merge left
1.3 km · 1 min
-
11
Turn right onto Middleton Road
1.6 km · 2 min · Middleton Road
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12
At the end of the road, turn right onto North Applegate Street
1872 ft · 38 sec · North Applegate Street
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13
Turn left onto Summit Street
2287 ft · 1 min · Summit Street
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14
Turn right onto South Vine Street
24 m · 3 sec · South Vine Street
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15
Arrive at your destination
0 m · 1 sec · South Vine Street
Car Route Details
A richer read on the saved driving route between Olive Branch and Winona.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
I 55 South
Merge slight left
96 mi · 01h 43m
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.
Clear leaving Olive Branch and Sunny near Winona.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Olive Branch to Winona?
The road trip is about 115.8 miles (186.3 km) and usually takes 02h 12m 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?
Courtland is a useful midpoint, sitting about 58 miles from Olive Branch and 57.8 miles from Winona.
How much longer is the road route than the straight-line distance?
The direct path is about 102.4 miles (164.8 km), while the road route adds roughly 13.4 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 CDT. If you want a more comfortable same-day return, try to leave by 2:04 PM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $15.45 one way or $30.90 round trip. Estimated CO2 is about 36.3 kg one way.
What should you check before leaving?
Before you leave, expect Clear around Olive Branch and Sunny near Winona.
Stop Ideas Near Courtland
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 Courtland.
Greenwood
Central Station
Flight Path Map
This map shows the direct air route between Olive Branch and Winona. Straight-line distance: 102.4 mi (164.8 km).
#1 Olive Branch
A city in DeSoto County, Mississippi.
| Population | 39,646 |
| Coordinates | 34.9617600, -89.8295300 |
| Altitude | 118 |
| Country | United States |
#2 Winona
City in Mississippi, United States
| Population | 3,830 |
| Coordinates | 33.4820700, -89.7281400 |
| Altitude | 116 |
| Country | United States |
End: Winona (-89.72814, 33.48207)
Estimated Travel Time
Distance: 186 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 51m |
| 40 mph (64.37 km/h) | 02h 53m |
| 50 mph (80.47 km/h) | 02h 18m |
| 60 mph (96.56 km/h) | 01h 55m |
| 70 mph (112.65 km/h) | 01h 39m |
| 80 mph (129 km/h) | 01h 26m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.79 | $15.45 | $30.90 |
| Mid-grade | $4.26 | $17.38 | $34.75 |
| Premium | $4.63 | $18.87 | $37.74 |
| Diesel | $5.42 | $22.09 | $44.19 |
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 Mississippi · May 14, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.