How far is Medford, OR from Winston, OR?
The driving distance from Medford, OR to Winston, OR is about 91.7 miles (147.6 km), with a travel time of about 01h 53m by car.
- The straight-line flight distance is about 61.4 miles (98.8 km).
- For a round trip, plan for roughly 03h 46m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM PDT.
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 53m.
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.
City in Oregon, USA
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 Medford and Winston.
Turn-by-Turn Driving Directions
Step-by-step road directions between Medford and Winston.
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1
Start on North Fir Street
580 ft · 18 sec · North Fir Street
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2
Turn right onto West 4th Street
1449 ft · 39 sec · West 4th Street
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3
Turn left onto North Riverside Avenue
1.1 mi · 3 min · North Riverside Avenue
-
4
Turn slight right onto Riverside Avenute Connection #1
582 ft · 23 sec · Riverside Avenute Connection #1
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5
Turn straight onto Crater Lake Highway
2240 ft · 1 min · Crater Lake Highway
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6
Take the exit left
957 ft · 23 sec
-
7
Merge slight left
82.7 mi · 1 hr 37 min
-
8
Take the exit slight right toward Round Prairie
910 ft · 20 sec
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9
Turn left onto Clarks Branch Road
591 ft · 13 sec · Clarks Branch Road
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10
At the end of the road, turn right onto Northeast Dole Road
1.2 km · 1 min · Northeast Dole Road
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11
At the end of the road, turn right onto Dillard Highway
5.2 mi · 8 min · Dillard Highway
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12
Continue on South Main Street
3200 ft · 56 sec · South Main Street
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13
Arrive at your destination
0 m · 1 sec · North Main Street
Car Route Details
A richer read on the saved driving route between Medford and Winston.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Crater Lake Highway
Merge slight left
82.7 mi · 01h 37m
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 Medford and Mostly Sunny near Winston.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Medford to Winston?
The road trip is about 91.7 miles (147.6 km) and usually takes 01h 53m 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?
Glendale is a useful midpoint, sitting about 45.9 miles from Medford and 45.9 miles from Winston.
How much longer is the road route than the straight-line distance?
The direct path is about 61.4 miles (98.8 km), while the road route adds roughly 30.3 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 PDT. If you want a more comfortable same-day return, try to leave by 2:44 PM PDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $16.04 one way or $32.08 round trip. Estimated CO2 is about 28.8 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Medford and Mostly Sunny near Winston.
Stop Ideas Near Glendale
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 Glendale.
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Medford, Oregon
Flight Path Map
This map shows the direct air route between Medford and Winston. Straight-line distance: 61.37 mi (98.77 km).
#1 Medford
The most populous city in Jackson County, Oregon.
| Population | 83,412 |
| Coordinates | 42.3265200, -122.8755900 |
| Altitude | 421 |
| Country | United States |
#2 Winston
City in Oregon, USA
| Population | 5,541 |
| Coordinates | 43.1223400, -123.4125700 |
| Altitude | 169 |
| Country | United States |
End: Winston (-123.41257, 43.12234)
Estimated Travel Time
Distance: 148 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 03m |
| 40 mph (64.37 km/h) | 02h 17m |
| 50 mph (80.47 km/h) | 01h 50m |
| 60 mph (96.56 km/h) | 01h 31m |
| 70 mph (112.65 km/h) | 01h 18m |
| 80 mph (129 km/h) | 01h 08m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.95 | $16.04 | $32.08 |
| Mid-grade | $5.34 | $17.30 | $34.59 |
| Premium | $5.57 | $18.03 | $36.07 |
| Diesel | $6.37 | $20.63 | $41.25 |
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 Oregon · May 05, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.