How far is Jackson, MS from Winona, MS?
The driving distance from Jackson, MS to Winona, MS is about 92.2 miles (148.4 km), with a travel time of about 01h 45m by car.
- The straight-line flight distance is about 85.9 miles (138.3 km).
- For a round trip, plan for roughly 03h 30m 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 45m.
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.
Town of the United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Jackson and Winona.
Turn-by-Turn Driving Directions
Step-by-step road directions between Jackson and Winona.
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1
Start on East Pearl Street
138 m · 15 sec · East Pearl Street
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2
Turn right onto South Lamar Street
115 m · 10 sec · South Lamar Street
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3
Enter the roundabout and take exit 1 toward East Capitol Street
2 m · 1 sec · East Capitol Street
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4
Exit the roundabout onto East Capitol Street
554 ft · 11 sec · East Capitol Street
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5
Enter the roundabout and take exit 2 toward East Capitol Street
16 m · 1 sec · East Capitol Street
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6
Exit the roundabout onto East Capitol Street
1139 ft · 33 sec · East Capitol Street
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7
At the end of the road, turn left onto North State Street
2.3 mi · 4 min · North State Street
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8
Turn slight right onto Old Canton Road
813 ft · 17 sec · Old Canton Road
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9
Turn right onto Lakeland Drive
1.3 km · 1 min · Lakeland Drive
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10
Turn left
2056 ft · 52 sec
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11
Merge slight left
85.4 mi · 1 hr 33 min
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12
Take the exit slight right toward US 82: Greenwood, Winona
1341 ft · 33 sec
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13
Keep slight right
151 m · 12 sec
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14
Merge slight left onto Dr Martin Luther King Jr Boulevard
2753 ft · 53 sec · Dr Martin Luther King Jr Boulevard
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15
Turn right onto Middleton Road
1.6 km · 2 min · Middleton Road
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16
At the end of the road, turn right onto North Applegate Street
1872 ft · 38 sec · North Applegate Street
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17
Turn left onto Summit Street
2287 ft · 1 min · Summit Street
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18
Turn right onto South Vine Street
24 m · 3 sec · South Vine Street
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19
Arrive at your destination
0 m · 1 sec · South Vine Street
Car Route Details
A richer read on the saved driving route between Jackson and Winona.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
Lakeland Drive
Merge slight left
85.4 mi · 01h 33m
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 Jackson and Mostly Sunny near Winona.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Jackson to Winona?
The road trip is about 92.2 miles (148.4 km) and usually takes 01h 45m 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?
Pickens is a useful midpoint, sitting about 46.2 miles from Jackson and 46 miles from Winona.
How much longer is the road route than the straight-line distance?
The direct path is about 85.9 miles (138.3 km), while the road route adds roughly 6.3 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 CDT. If you want a more comfortable same-day return, try to leave by 3:00 PM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $12.31 one way or $24.62 round trip. Estimated CO2 is about 28.9 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Jackson and Mostly Sunny near Winona.
Stop Ideas Near Pickens
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 Pickens.
Yazoo City
Union Station
Greenwood
Vicksburg, MS
Flight Path Map
This map shows the direct air route between Jackson and Winona. Straight-line distance: 85.94 mi (138.31 km).
#1 Jackson
The capital and most populous city of Mississippi.
| Population | 157,821 |
| Coordinates | 32.2987600, -90.1848100 |
| Altitude | 85 |
| 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: 148 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 04m |
| 40 mph (64.37 km/h) | 02h 18m |
| 50 mph (80.47 km/h) | 01h 50m |
| 60 mph (96.56 km/h) | 01h 32m |
| 70 mph (112.65 km/h) | 01h 19m |
| 80 mph (129 km/h) | 01h 09m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.79 | $12.31 | $24.62 |
| Mid-grade | $4.26 | $13.84 | $27.68 |
| Premium | $4.63 | $15.03 | $30.06 |
| Diesel | $5.42 | $17.60 | $35.20 |
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 · Apr 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.