How far is Winona, MS from Olive Branch, MS?
The driving distance from Winona, MS to Olive Branch, MS is about 115.1 miles (185.3 km), with a travel time of about 01h 49m by car.
- The straight-line flight distance is about 102.4 miles (164.8 km).
- For a round trip, plan for roughly 03h 39m 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 01h 49m.
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.
Driving Route Map
The map below follows the saved road route between Winona and Olive Branch.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winona and Olive Branch.
-
1
Start on South Vine Street
24 m · 9 sec · South Vine Street
-
2
Turn left onto Summit Street
2287 ft · 1 min · Summit Street
-
3
Turn right onto North Applegate Street
1872 ft · 39 sec · North Applegate Street
-
4
Turn left onto Middleton Road
1.6 km · 2 min · Middleton Road
-
5
Turn left onto Dr Martin Luther King Jr Boulevard
2915 ft · 55 sec · Dr Martin Luther King Jr Boulevard
-
6
Take the exit slight right
1868 ft · 46 sec
-
7
Merge slight left
96 mi · 1 hr 43 min
-
8
Take the exit slight right toward I 69 South: Tunica
1599 ft · 39 sec
-
9
Keep slight right to continue on I 269 East: Nashville
2730 ft · 1 min
-
10
Merge slight left onto I 269 East: Nashville
8.7 mi · 9 min
-
11
Take the exit slight right toward MS 305: Independence, Olive Branch, Lewisburg
1865 ft · 53 sec
-
12
Turn left onto MS 305
6.4 mi · 11 min · MS 305
-
13
Turn right onto Goodman Road
79 m · 5 sec · Goodman Road
-
14
Arrive at your destination
0 m · 1 sec · Goodman Road
Car Route Details
A richer read on the saved driving route between Winona and Olive Branch.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
Dr Martin Luther King Jr Boulevard
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.
Sunny leaving Winona and Clear near Olive Branch.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winona to Olive Branch?
The road trip is about 115.1 miles (185.3 km) and usually takes 01h 49m 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 57.6 miles from Winona and 57.5 miles from Olive Branch.
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 12.7 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 2:50 PM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $15.38 one way or $30.75 round trip. Estimated CO2 is about 36.1 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Winona and Clear near Olive Branch.
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 Winona and Olive Branch. Straight-line distance: 102.4 mi (164.8 km).
#1 Winona
City in Mississippi, United States
| Population | 3,830 |
| Coordinates | 33.4820700, -89.7281400 |
| Altitude | 116 |
| Country | United States |
#2 Olive Branch
A city in DeSoto County, Mississippi.
| Population | 39,646 |
| Coordinates | 34.9617600, -89.8295300 |
| Altitude | 118 |
| Country | United States |
End: Goodman Road (-89.829531, 34.961856)
Estimated Travel Time
Distance: 185 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 50m |
| 40 mph (64.37 km/h) | 02h 52m |
| 50 mph (80.47 km/h) | 02h 18m |
| 60 mph (96.56 km/h) | 01h 55m |
| 70 mph (112.65 km/h) | 01h 38m |
| 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 | $15.38 | $30.75 |
| Mid-grade | $4.26 | $17.29 | $34.58 |
| Premium | $4.63 | $18.78 | $37.56 |
| Diesel | $5.42 | $21.98 | $43.97 |
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.