How far is Tupelo, MS from Winona, MS?
The driving distance from Tupelo, MS to Winona, MS is about 98.4 miles (158.4 km), with a travel time of about 02h 21m by car.
- The straight-line flight distance is about 79.5 miles (128 km).
- For a round trip, plan for roughly 04h 43m 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 21m.
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.
Village in the United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Tupelo and Winona.
Turn-by-Turn Driving Directions
Step-by-step road directions between Tupelo and Winona.
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1
Start on North Spring Street
21 m · 8 sec · North Spring Street
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2
Turn left onto Court Street
85 m · 18 sec · Court Street
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3
Turn left onto North Broadway Street
91 m · 17 sec · North Broadway Street
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4
Turn right onto West Main Street
2.9 mi · 7 min · West Main Street
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5
Turn left
1533 ft · 1 min
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6
At the end of the road, turn left onto Natchez Trace Parkway
45.4 mi · 1 hr 8 min · Natchez Trace Parkway
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7
Turn right onto County Road 285
691 ft · 31 sec · County Road 285
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8
At the end of the road, turn left
9.5 mi · 14 min
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9
Take the ramp slight right
2 mi · 4 min
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10
Continue straight
36.8 mi · 43 min
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11
Turn left onto Greensboro Street
1.1 mi · 3 min · Greensboro Street
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12
At the end of the road, turn left onto North Union Avenue
76 m · 9 sec · North Union Avenue
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13
Turn right onto Liberty Street
814 ft · 22 sec · Liberty Street
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14
Turn left onto North Front Street
141 m · 17 sec · North Front Street
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15
Turn right onto Summit Street
53 m · 10 sec · Summit Street
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16
Turn left onto South Vine Street
24 m · 3 sec · South Vine Street
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17
Arrive at your destination
0 m · 1 sec · South Vine Street
Car Route Details
A richer read on the saved driving route between Tupelo and Winona.
Straightforward drive
The saved road route has a manageable number of maneuvers and should be easy to follow with normal attention to signs.
Natchez Trace Parkway
At the end of the road, turn left onto Natchez Trace Parkway
45.4 mi · 01h 08m
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 Tupelo 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 Tupelo to Winona?
The road trip is about 98.4 miles (158.4 km) and usually takes 02h 21m 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?
Mantee is a useful midpoint, sitting about 49.2 miles from Tupelo and 49.2 miles from Winona.
How much longer is the road route than the straight-line distance?
The direct path is about 79.5 miles (128 km), while the road route adds roughly 18.9 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 1:46 PM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $13.14 one way or $26.28 round trip. Estimated CO2 is about 30.8 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Tupelo and Mostly Sunny near Winona.
Stop Ideas Near Mantee
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 Mantee.
Greenwood
Flight Path Map
This map shows the direct air route between Tupelo and Winona. Straight-line distance: 79.51 mi (127.96 km).
#1 Tupelo
City in and county seat of Lee County, Mississippi, United States
| Population | 38,303 |
| Coordinates | 34.2580700, -88.7046400 |
| 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: 158 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 16m |
| 40 mph (64.37 km/h) | 02h 27m |
| 50 mph (80.47 km/h) | 01h 58m |
| 60 mph (96.56 km/h) | 01h 38m |
| 70 mph (112.65 km/h) | 01h 24m |
| 80 mph (129 km/h) | 01h 13m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.79 | $13.14 | $26.28 |
| Mid-grade | $4.26 | $14.78 | $29.56 |
| Premium | $4.63 | $16.05 | $32.10 |
| Diesel | $5.42 | $18.79 | $37.58 |
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.