Traveling from Winona to Oxford, Mississippi, covers 190.3 miles and takes approximately 3 hours and 53 minutes. Because this journey is manageable in a single day, it works well as a straightforward day trip without the need for an overnight stay. You will spend the vast majority of your time on highways, primarily utilizing I-55, US-84, and Gloster Road. Budgeting around $29 for fuel should comfortably cover your gas needs for the duration of the trip. Both locations reside within the Southeast region, offering a consistent feel as you transition between these Mississippi hubs. Use this route if you prefer a direct, highway-focused drive that gets you to your destination efficiently.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Break Rhythm
1 planned break
A short stop every 2 to 3 hours is enough for this drive.
Midpoint
95.1 miles from Winona, MS
A natural place for your longest stop of the day
, about 1h 46m into the drive
.
Main Roads
Road
Distance
Duration
I 55
145.6 mi
2h 38m
US 84
22.7 mi
26m
Gloster Road
6.5 mi
15m
Oxford-Meadville Road
6.3 mi
15m
Yap 3 Road
2.6 mi
6m
US 98
1.9 mi
2m
MS 184
1.4 mi
2m
Middleton Road
1 mi
1m
Longest stretch:
I 55
— 145.6 mi, about 2h 38m
Turn-by-Turn Driving Directions
Step-by-step road directions between Winona, MS and Oxford, MS.
1
Start on South Vine Street
78 ft·8 sec·South Vine Street
2
Turn left onto Summit Street
0.4 mi·1 min·Summit Street
3
Turn right onto US 51
0.4 mi·39 sec·North Applegate Street
4
Turn left onto MS 182
1.0 mi·1 min·Middleton Road
5
Turn left onto US 82
0.7 mi·1 min·Dr Martin Luther King Jr Boulevard
6
Take the exit
0.3 mi·46 sec
7
Merge onto I 55
92 mi·1 hr 40 min·I 55
8
Keep slight left at fork onto I 55
54 mi·57 min·I 55
Toward I 55 South: McComb, New Orleans
9
Take the exit
0.3 mi·35 sec
Toward US 84: South Brookhaven, Natchez
10
Keep slight right at fork
409 ft·9 sec
Toward US 84: South Brookhaven, Natchez
11
Merge onto US 84
23 mi·26 min·US 84
12
Turn left onto MS 184
1.4 mi·2 min·MS 184
13
Turn left onto US 98
1.9 mi·2 min·US 98
14
Turn right onto Yap 3 Road
2.6 mi·6 min·Yap 3 Road
15
Continue on Gloster Road
3.8 mi·9 min·Gloster Road
16
At end of road, turn right onto Gloster Road
2.8 mi·6 min·Gloster Road
17
Continue on Oxford-Meadville Road
6.3 mi·15 min·Oxford-Meadville Road
18
Arrive at destination
Oxford-Meadville Road
Trip Plan
Since this route is a relatively short drive, you have plenty of flexibility in your departure time to avoid heavy traffic. Plan for at least one stop during the 3-hour and 53-minute journey to keep your energy levels up and stretch your legs. Because the longest segment spans 145.6 miles on I-55, ensure your fuel tank is topped off before hitting that stretch to avoid unnecessary stops. Keep a close watch on your navigation as you transition from the interstate onto local roads like Gloster Road, as the turn-off timing is key. Taking advantage of the route's simplicity allows you to focus on an easy, stress-free arrival in Oxford.
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 95.1 miles from Winona, MS, or about 1h 46m into the drive.
The longest continuous stretch on this route runs about 145.6 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 42 miles or 48m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 95.1 miles or 1h 46m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 2h 53m
Traffic, exits, and arrival timing usually matter more near Oxford, MS than in the middle of the route.
Before You Leave
+
Open the route before leaving Winona, 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 Winona, MS
This is one driving day of about 190.3 miles and 3h 53m.
Your first comfortable stop window is around 42 miles from Winona, 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 I 55 for about 145.6 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 14
5 decision points cluster between mile 0.8 and 171.6 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
4
0.8 mi into trip|~1m in|MS 182 / Middleton Road
Turn left onto MS 182 / Middleton Road
Navigation decision point
6
94.7 mi into trip|~1h 46m in|I 55
Keep slight left at fork onto I 55 toward I 55 South: McComb, New Orleans
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Toward I 55 South: McComb, New Orleans
5
148.5 mi into trip|~2h 44m in
Take the exit toward US 84: South Brookhaven, Natchez
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Toward US 84: South Brookhaven, Natchez
7
148.8 mi into trip|~2h 44m in
Keep slight right at fork toward US 84: South Brookhaven, Natchez
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Toward US 84: South Brookhaven, Natchez
4
171.6 mi into trip|~3h 11m in|MS 184
Turn left onto MS 184
Navigation decision point
Fuel & Cost
Regular Gas
$28.74 one way
$57.48 round trip
$3.84/gal25.4 MPG avg67 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.21
$31.55
$63.10
premium
$4.56
$34.16
$68.31
diesel
$5.61
$42.02
$84.03
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$29
Meals
$25–$50
Total
$54–$79
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 66.6 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $20 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
57.1
0
$19.98
$9.13
Efficient EV
47.6
0
$16.65
$7.61
EV Truck/SUV
76.1
0
$26.64
$12.18
Gas CO2
67 kg
EV CO2
22 kg (67% 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 Apr 20, 2026
Origin
Winona, MS
Late night
in Winona on Tuesday
Local time
5:42 AM
CDT
Current temp
83°F
Unavailable
Live forecast
Destination
Oxford, MS
Late night
in Oxford on Tuesday
Local time
5:42 AM
CDT
Current temp
83°F
Unavailable
Live forecast
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
3h 53m on the road
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
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 91.8
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a highly efficient commute, as 90% of this route is comprised of highway travel. The drive is defined by a significant, uninterrupted 145.6-mile stretch along I-55, which allows for steady, consistent progress behind the wheel. While the interstate dominates the majority of the journey, the transition onto US-84 and Gloster Road provides a shift in pace as you approach your destination. This is essentially a highway-focused drive, prioritizing speed and connectivity over winding backroads. You will find that the road maintains a predictable rhythm, making it an ideal choice for those who want to cover ground quickly.
90% highway — fuel and pacing are the main things to plan.
18 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 145.6 mi on I 55.
How Hard Is This Drive?
5/10
This is a straightforward highway drive that stays mostly on I 55 and US 84. You will hit about 14 points where you need to pay attention to lane position or signs. The trickiest moment comes around 0.8 miles in near MS 182 / Middleton Road.
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 190.3 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 0.8 miles (MS 182 / Middleton Road): Navigation decision point; at 94.7 miles (I 55): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 148.5 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Winona, MS and Oxford, MS, road signs point toward New Orleans and Natchez.
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.
Oxford is a historic, picturesque town in North Central Mississippi. With its scenic town square, acclaimed restaurants, unique boutiques, oak-shaded neighborhoods, and friendly people, Oxford is the model Southern town. Named after Oxford, England, in hopes of attracting a university, the town was selected as the home of the University of Mississippi in 1848, which dominates life here today.
Doable as a same-day drive at 3h 53m. Total distance: 190.3 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
3h 53m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (90%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 145.6 miles on I 55. The full list of main roads is in the Roads section above.
We did not find dedicated rest areas on this route. For a drive this long, plan bathroom and stretch breaks around gas stations, fast-food stops, or small-town downtowns — check the Nearby Places section for options.
Yes, with realistic expectations. Build in a stop roughly every 2 hours, have snacks and activities ready, and check the Nearby Places tabs for kid-friendly stops along the way.
The main spots that need attention: at 0.8 miles (MS 182 / Middleton Road): Navigation decision point; at 94.7 miles (I 55): Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 148.5 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 3.9 hours each way, an in-and-out day trip would put you behind the wheel for 7.8 hours — manageable with a long break at Oxford, MS, but most travelers stay overnight.
