Gulfport to Winona is 247.8 miles and takes about 4 hours 57 minutes via US 49 and I-55, with a fuel budget near $36 and enough daylight to finish in a day. This drive primarily stays within Mississippi, moving from the Southeast region up into the state's interior. Expect a straightforward trip with a significant portion on highways, making it a practical option for a single-day excursion. It's a good choice if you're looking for an efficient way to cover ground within the state without extensive planning.
Trip Pace
Same-day drive is realistic
A same-day return is possible, but it will make for a full day on the road.
Break Rhythm
1 planned break
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
123.9 miles from Gulfport, MS
A natural place for your longest stop of the day
, about 2h 35m into the drive
.
Main Roads
Road
Distance
Duration
US 49
95.2 mi
2h
I 55
89.8 mi
1h 38m
25th Avenue
60.1 mi
1h 14m
Middleton Road
1 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
South Vine Street
<0.1 mi
<1m
Longest stretch:
US 49
— 95.2 mi, about 2h
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 Gulfport, MS and Winona, MS.
1
Start on US 49
60 mi·1 hr 14 min·25th Avenue
Use the straight lane.
2
Continue on US 49
2.4 mi·2 min·US 49
Use the straight / slight right lanes.
3
Turn straight onto US 49
10 mi·16 min·US 49
Use the straight lane.
4
Continue on US 49; MS 42
5.4 mi·6 min·US 49; MS 42
Use the straight lane.
5
Continue on US 49
5.3 mi·6 min·US 49
Use the straight lane.
6
Continue on US 49
0.2 mi·14 sec·US 49
Use the straight lane.
7
Continue on US 49
4.2 mi·4 min·US 49
Use the straight lane.
8
Continue on US 49
66 mi·1 hr 20 min·US 49
Use the straight lane.
9
Take the exit onto US 49
0.2 mi·21 sec·US 49
10
Keep slight left at fork onto US 49
0.7 mi·1 min·US 49
Toward Jackson
11
Keep slight right at fork onto US 49
0.9 mi·1 min·US 49
12
Merge onto I 55
90 mi·1 hr 38 min·I 55
13
Take the exit
0.3 mi·32 sec
Toward US 82: Greenwood, Winona
14
Keep slight right at fork
497 ft·12 sec
15
Merge onto US 82
0.5 mi·52 sec·Dr Martin Luther King Jr Boulevard
16
Turn right onto MS 182
1.0 mi·1 min·Middleton Road
17
At end of road, turn right onto US 51
0.4 mi·38 sec·North Applegate Street
18
Turn left onto Summit Street
0.4 mi·1 min·Summit Street
19
Turn right onto South Vine Street
78 ft·3 sec·South Vine Street
20
Arrive at destination
South Vine Street
Trip Plan
Given the 4 hour 57 minute drive time, leaving in the morning should allow you to reach Winona comfortably before evening. With only one recommended stop, you have flexibility in pacing your journey. Keep an eye on your fuel gauge, especially during the 95.2-mile stretch on US 49, as services might be less frequent in certain sections. The $36 fuel estimate is helpful for budgeting, but it's always wise to have a little extra. Since this is a manageable one-day drive, you can adjust your departure time based on your preference for an earlier or later arrival.
Morning Departure
An early start around 7-8 AM gets you there with plenty of daylight left.
Evening Departure
A late afternoon start means arriving after dark. Morning is better.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 123.9 miles from Gulfport, MS, or about 2h 35m into the drive.
The longest continuous stretch on this route runs about 95.2 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 55 miles or 1h 7m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 123.9 miles or 2h 35m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 4h 6m
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 Gulfport, MS so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Gulfport, MS
This is one driving day of about 247.8 miles and 4h 57m.
Your first comfortable stop window is around 55 miles from Gulfport, MS.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 1 real break rather than only quick fuel stops.
The longest stretch is on US 49 for about 95.2 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 12
5 decision points cluster between mile 153.7 and 247 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
153.7 mi into trip|~3h 11m in|US 49
Keep slight left at fork onto US 49 toward Jackson
Highway fork - watch signs carefully
Toward Jackson
4
154.4 mi into trip|~3h 13m in|US 49
Keep slight right at fork onto US 49
Highway fork - watch signs carefully
5
245.1 mi into trip|~4h 52m 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
5
245.4 mi into trip|~4h 53m in
Keep slight right at fork
Highway fork - watch signs carefully
5
247 mi into trip|~4h 55m in|US 51 / North Applegate Street
At end of road, turn right onto US 51 / North Applegate Street
Navigation decision point
Fuel & Cost
Regular Gas
$37.93 one way
$75.86 round trip
$3.89/gal25.4 MPG avg87 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.31
$42.01
$84.02
premium
$4.65
$45.36
$90.71
diesel
$6.28
$61.23
$122.46
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$38
Meals
$25–$50
Total
$63–$88
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 86.7 kg one way.
Prices: EIA weekly data, 2026-10-19.
Driving Electric?
About $26 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
74.3
0
$26.02
$11.89
Efficient EV
62
0
$21.68
$9.91
EV Truck/SUV
99.1
1
$34.69
$15.86
Gas CO2
87 kg
EV CO2
29 kg (67% less)
Plan for 0 charging stops, roughly every 270 miles. Allow 25-40 minutes per stop at a DC fast charger.
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 Oct 19, 2026
Origin
Gulfport, MS
Morning
in Gulfport on Thursday
Local time
6:11 AM
CDT
Current temp
75°F
Sunny
NE 10 mph0% chanceLive forecast
Destination
Winona, MS
Morning
in Winona on Thursday
Local time
6:11 AM
CDT
Current temp
75°F
Sunny
E 5 mph0% chanceLive forecast
45°F
Sumrall, MS
124 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
Very similar conditions
Both ends of the route are sitting at about the same temperature right now.
Road read
4h 57m on the road
An early start around 7-8 AM gets you there with plenty of daylight left.
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...
4 mi from route
~11 min detour
Free
near mile 162.3
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This route is mostly highway, with 75% of the drive on major roads. You'll experience a long stretch of 95.2 miles on US 49 before transitioning. Expect a shift from highway cruising to surface streets as you approach your destination. The prevalence of highway driving means you'll encounter frequent exits and merges.
75% highway — fuel and pacing are the main things to plan.
20 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 95.2 mi on US 49.
How Hard Is This Drive?
8/10
This is a straightforward highway drive that stays mostly on US 49 and I 55. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 153.7 miles in near US 49.
Driving Effort8/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This is a demanding drive. With 12 significant decision points across 247.8 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 153.7 miles (US 49): Highway fork - watch signs carefully; at 154.4 miles (US 49): Highway fork - watch signs carefully; at 245.1 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Elevation Profile
Mostly flat terrain
395 ft20 ft
Total Climb
523 ft
Total Descent
149 ft
Highest Point
395 ft
~247.8 mi in
Elevation Range
374 ft
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
On the drive from Gulfport, MS to Winona, MS, road signs begin pointing toward Jackson along the way.
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 4h 57m. Total distance: 247.8 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
4h 57m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (75%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 95.2 miles on US 49. The full list of main roads is in the Roads section above.
Yes — we found about 1 rest area or service plaza within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Winona, MS before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 1 meaningful breaks. There are 1 rest area along the route for bathroom stops.
The main spots that need attention: at 153.7 miles (US 49): Highway fork - watch signs carefully; at 154.4 miles (US 49): Highway fork - watch signs carefully; at 245.1 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Yes — Medgar and Myrlie Evers Home National Monument. See the National Parks section for detour distances and tips on detours.
Possible but tiring. At 5.0 hours each way, an in-and-out day trip would put you behind the wheel for 9.9 hours — manageable with a long break at Winona, MS, but most travelers stay overnight.
