How far is Winston, OR from Medford, OR?
The driving distance from Winston, OR to Medford, OR is about 92.4 miles (148.7 km), with a travel time of about 01h 37m by car.
- The straight-line flight distance is about 61.4 miles (98.8 km).
- For a round trip, plan for roughly 03h 14m 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 37m.
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
Driving Route Map
The map below follows the saved road route between Winston and Medford.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winston and Medford.
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1
Start on North Main Street
3200 ft · 56 sec · North Main Street
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2
Continue on Dillard Highway
5.2 mi · 8 min · Dillard Highway
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3
Turn left onto Northeast Dole Road
1.2 km · 1 min · Northeast Dole Road
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4
Turn left onto Clarks Branch Road
56 m · 4 sec · Clarks Branch Road
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5
Take the ramp right
1372 ft · 34 sec
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6
Merge slight left
82.6 mi · 1 hr 37 min
-
7
Take the exit slight right toward OR 62: Crater Lake Highway, Medford, Klamath Falls
1743 ft · 46 sec
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8
Turn right onto Crater Lake Highway
1973 ft · 52 sec · Crater Lake Highway
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9
Turn left onto Court Street
1.2 km · 2 min · Court Street
-
10
Continue on North Central Avenue
2827 ft · 1 min · North Central Avenue
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11
Turn right onto East 4th Street
673 ft · 24 sec · East 4th Street
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12
Turn left onto North Fir Street
580 ft · 16 sec · North Fir Street
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13
Arrive at your destination
0 m · 1 sec · North Fir Street
Car Route Details
A richer read on the saved driving route between Winston and Medford.
Straightforward drive
The saved road route has a manageable number of maneuvers and should be easy to follow with normal attention to signs.
Clarks Branch Road
Merge slight left
82.6 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 Winston and Mostly Sunny near Medford.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winston to Medford?
The road trip is about 92.4 miles (148.7 km) and usually takes 01h 37m 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 45.8 miles from Winston and 46.5 miles from Medford.
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 31 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 3:16 PM PDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $16.14 one way or $32.28 round trip. Estimated CO2 is about 29 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Winston and Mostly Sunny near Medford.
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 Winston and Medford. Straight-line distance: 61.37 mi (98.77 km).
#1 Winston
City in Oregon, USA
| Population | 5,541 |
| Coordinates | 43.1223400, -123.4125700 |
| Altitude | 169 |
| Country | United States |
#2 Medford
The most populous city in Jackson County, Oregon.
| Population | 83,412 |
| Coordinates | 42.3265200, -122.8755900 |
| Altitude | 421 |
| Country | United States |
End: North Fir Street (-122.875345, 42.326645)
Estimated Travel Time
Distance: 149 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 04m |
| 40 mph (64.37 km/h) | 02h 18m |
| 50 mph (80.47 km/h) | 01h 50m |
| 60 mph (96.56 km/h) | 01h 32m |
| 70 mph (112.65 km/h) | 01h 19m |
| 80 mph (129 km/h) | 01h 09m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.95 | $16.14 | $32.28 |
| Mid-grade | $5.34 | $17.40 | $34.80 |
| Premium | $5.57 | $18.15 | $36.29 |
| Diesel | $6.37 | $20.75 | $41.51 |
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.