The drive from Jackson, MS to Winona, MS covers 92.2 miles and takes about 1h 45m behind the wheel.
This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on I 55, North State Street, Middleton Road for much of the mileage,
and the overall profile is mostly highway.
The longest uninterrupted segment is about 85.4 miles on I 55.
At current regular gas prices, budget about $13.51 one way before food or hotel costs.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
46.1 miles from Jackson, MS
A natural place for your longest stop of the day
, about 53m into the drive
.
Main Roads
Road
Distance
Duration
I 55
85.4 mi
1h 32m
North State Street
2.3 mi
3m
Middleton Road
1 mi
1m
Lakeland Drive
0.8 mi
1m
Dr Martin Luther King Jr Boulevard
0.5 mi
<1m
Summit Street
0.4 mi
1m
North Applegate Street
0.4 mi
<1m
East Capitol Street
0.3 mi
<1m
Longest stretch:
I 55
— 85.4 mi, about 1h 32m
Traffic on I-55
Hour-of-day weekday pattern from 90 FHWA count stations on your route.
Peak
4 PM
~3,260 veh/hr typical
Quietest
2 AM
~182 veh/hr
Peak-to-quiet ratio
17.9×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 100 weeks of 2023 FHWA Travel Monitoring Analysis System data. Weekday hours only (Mon–Fri).
Turn-by-Turn Driving Directions
Step-by-step road directions between Jackson, MS and Winona, MS.
1
Start on East Pearl Street
452 ft·15 sec·East Pearl Street
2
Turn right onto South Lamar Street
378 ft·10 sec·South Lamar Street
3
Enter roundabout onto East Capitol Street
7 ft·0 sec·East Capitol Street
4
Continue on East Capitol Street
0.1 mi·11 sec·East Capitol Street
5
Enter roundabout onto East Capitol Street
51 ft·1 sec·East Capitol Street
6
Continue on East Capitol Street
0.2 mi·32 sec·East Capitol Street
7
At end of road, turn left onto US 51
2.3 mi·3 min·North State Street
8
Turn slight right onto Old Canton Road
0.2 mi·16 sec·Old Canton Road
9
Turn right onto Lakeland Drive
0.8 mi·1 min·Lakeland Drive
10
Turn left
0.4 mi·52 sec
11
Merge onto I 55
85 mi·1 hr 32 min·I 55
12
Take the exit
0.3 mi·32 sec
Toward US 82: Greenwood, Winona
13
Keep slight right at fork
497 ft·12 sec
14
Merge onto US 82
0.5 mi·52 sec·Dr Martin Luther King Jr Boulevard
15
Turn right onto MS 182
1.0 mi·1 min·Middleton Road
16
At end of road, turn right onto US 51
0.4 mi·38 sec·North Applegate Street
17
Turn left onto Summit Street
0.4 mi·1 min·Summit Street
18
Turn right onto South Vine Street
78 ft·3 sec·South Vine Street
19
Arrive at destination
South Vine Street
Trip Plan
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 46.1 miles from Jackson, MS, or about 53m into the drive.
The longest continuous stretch on this route runs about 85.4 miles.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 20 miles or 24m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 46.1 miles or 53m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 25m
Traffic, exits, and arrival timing usually matter more near Winona, MS than in the middle of the route.
Before You Leave
+
Open the route before leaving Jackson, MS so your first major turns are already loaded.
Day 1
Settle into the route from Jackson, MS
This is one driving day of about 92.2 miles and 1h 45m.
Your first comfortable stop window is around 20 miles from Jackson, MS.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on I 55 for about 85.4 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
The midpoint is around 46.1 miles from Jackson, MS, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel check
Top up before I 55 if your tank is already low. That segment runs about 85.4 miles.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Heads-up: tricky spots
5 of 14
5 decision points cluster between mile 0.1 and 89.5 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
0.1 mi into trip|~0m in|South Lamar Street
Turn right onto South Lamar Street
Navigation decision point
5
0.2 mi into trip|~0m in|East Capitol Street
Enter roundabout onto East Capitol Street
Roundabout - know your exit number before entering
5
0.3 mi into trip|~0m in|East Capitol Street
Enter roundabout onto East Capitol Street
Roundabout - know your exit number before entering
5
0.5 mi into trip|~1m in|US 51 / North State Street
At end of road, turn left onto US 51 / North State Street
Navigation decision point
5
89.5 mi into trip|~1h 40m in
Take the exit toward US 82: Greenwood, Winona
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Toward US 82: Greenwood, Winona
Fuel & Cost
Regular Gas
$13.51 one way
$27.01 round trip
$3.72/gal25.4 MPG avg32 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.13
$15.00
$29.99
premium
$4.49
$16.28
$32.57
diesel
$5.60
$20.32
$40.65
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$14
Meals
$25–$50
Total
$39–$64
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 32.3 kg one way.
Prices: EIA weekly data, 2026-08-31.
Driving Electric?
About $10 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
27.7
0
$9.68
$4.43
Efficient EV
23.1
0
$8.07
$3.69
EV Truck/SUV
36.9
0
$12.91
$5.90
Gas CO2
32 kg
EV CO2
11 kg (66% less)
This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive.
Forecast as of Sep 2, 2026
Origin
Jackson, MS
Morning
in Jackson on Friday
Local time
11:18 AM
CDT
Current temp
76°F
Mostly Clear
S 0 to 5 mph0% chanceLive forecast
Heat Advisory
Heat Advisory issued September 1 at 8:27PM CDT until September 2 at 7:00PM CDT by NWS Jackson MS
Heat Advisory
Heat Advisory issued September 1 at 7:45PM CDT until September 5 at 8:00PM CDT by NWS Memphis TN
Destination
Winona, MS
Morning
in Winona on Friday
Local time
11:18 AM
CDT
Current temp
73°F
Mostly Clear
0 mph1% chanceLive forecast
Heat Advisory
Heat Advisory issued September 1 at 8:27PM CDT until September 2 at 7:00PM CDT by NWS Jackson MS
Heat Advisory
Heat Advisory issued September 1 at 7:45PM CDT until September 5 at 8:00PM CDT by NWS Memphis TN
72°F
Richton, MS
46 mi in
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
3 degrees cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
1h 45m on the road
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
National Parks Near This Route
Worth a detour if your schedule allows.
Medgar and Myrlie Evers Home National Monument
National Monument
Medgar and Myrlie Evers were partners in the civil rights struggle. The assassination of Medgar Evers in the carport of their home on June 12, 1963, was the first murder of a nationally significant le...
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
92.2 mi in 1h 45m, mostly highway — 85.4 mi of that is on I 55.
93% highway — fuel and pacing are the main things to plan.
19 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 85.4 mi on I 55.
How Hard Is This Drive?
5/10
This is a straightforward highway drive that stays mostly on I 55 and North State Street. You will hit about 14 points where you need to pay attention to lane position or signs. The trickiest moment comes around 0.1 miles in near South Lamar Street.
Driving Effort5/10
Moderate - straightforward overall, but long enough or busy enough to require pacing
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 92.2 miles you will encounter 14 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
Where does it get tricky?
The main spots that need attention: at 0.1 miles (South Lamar Street): Navigation decision point; at 0.2 miles (East Capitol Street): Roundabout - know your exit number before entering; at 0.3 miles (East Capitol Street): Roundabout - know your exit number before entering.
Jackson is the capital of the state of Mississippi. While it may not offer much in terms of tourism today, Jackson can be used as a stopover for getting to other parts of the state or further.
Top landmarks
•Mississippi State Capitol — state capitol building of the U.S. state of Mississippi
•Union Station — train station in Jackson, Mississippi
•Medgar and Myrlie Evers Home National Monument — national monument in Jackson, Mississippi, United States
Winona, known as the Island City, is a historic river and college town in Southeastern Minnesota, located on a large sandbar among the bluffs along the Mississippi River. It is about 110 miles southeast of the Twin Cities.
Doable as a same-day drive at 1h 45m. Total distance: 92.2 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 45m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (93%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 85.4 miles on I 55. The full list of main roads is in the Roads section above.
Yes. At under 2 hours behind the wheel, this works well for families — plan one quick stop if you have younger kids.
The main spots that need attention: at 0.1 miles (South Lamar Street): Navigation decision point; at 0.2 miles (East Capitol Street): Roundabout - know your exit number before entering; at 0.3 miles (East Capitol Street): Roundabout - know your exit number before entering.
Yes — Medgar and Myrlie Evers Home National Monument. See the National Parks section for detour distances and tips on detours.
Yes. A round trip is manageable in a single day if you plan a break at Winona, MS before heading back.
