How far is Medford, OR from Milton-Freewater, OR?
The driving distance from Medford, OR to Milton-Freewater, OR is about 444 miles (714.6 km), with a travel time of about 09h 38m by car.
- The straight-line flight distance is about 334 miles (537.5 km).
- For a round trip, plan for roughly 19h 16m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 7:30 AM PDT.
Reverse, save, or send this route
This drive is better planned with a longer stop or an overnight stay. Copy the route link, send it to another device, or print a clean version before you head out.
This drive is better planned with a longer stop or an overnight stay.
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 09h 38m.
Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
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.
Partly Sunny then Chance Light Rain
Partly Sunny
Driving Route Map
The map below follows the saved road route between Medford and Milton-Freewater.
Turn-by-Turn Driving Directions
Step-by-step road directions between Medford and Milton-Freewater.
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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
2226 ft · 54 sec · West 4th Street
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3
Continue on Biddle Road
1.3 mi · 2 min · Biddle Road
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4
Take the ramp right
1221 ft · 36 sec
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5
Merge slight left onto Crater Lake Highway
2251 ft · 52 sec · Crater Lake Highway
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6
Turn straight onto Rogue Valley Expressway
4.5 mi · 6 min · Rogue Valley Expressway
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7
At the end of the road, turn left onto Crater Lake Highway
49.6 mi · 1 hr 12 min · Crater Lake Highway
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8
Turn straight onto Diamond Lake Highway
23.8 mi · 35 min · Diamond Lake Highway
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9
At the end of the road, turn right onto North Umpqua Highway
2.9 mi · 4 min · North Umpqua Highway
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10
Keep slight left to continue on North Umpqua Highway
66 m · 4 sec · North Umpqua Highway
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11
Continue on East Diamond Lake Highway
8.4 mi · 12 min · East Diamond Lake Highway
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12
Continue on State Highway 138
6.3 mi · 9 min · State Highway 138
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13
Turn left onto The Dalles-California Highway
71.2 mi · 1 hr 29 min · The Dalles-California Highway
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14
Continue on Bend Parkway
7.3 mi · 12 min · Bend Parkway
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15
Continue on The Dalles-California Highway
38.2 mi · 53 min · The Dalles-California Highway
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16
Continue on 5th Street
1.4 km · 3 min · 5th Street
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17
Turn right onto Northeast 6th Street
1259 ft · 31 sec · Northeast 6th Street
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18
Continue on The Dalles-California Highway
24.6 mi · 29 min · The Dalles-California Highway
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19
Turn straight onto Sherman Highway
12.3 mi · 17 min · Sherman Highway
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20
Continue on E Street
2151 ft · 53 sec · E Street
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21
Continue on Sherman Highway
55.4 mi · 1 hr 13 min · Sherman Highway
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22
Take the exit right
1357 ft · 33 sec
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23
Merge slight left onto Columbia River Highway
62.7 mi · 1 hr 7 min · Columbia River Highway
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24
Continue on Old Oregon Trail Highway
43.1 mi · 47 min · Old Oregon Trail Highway
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25
Take the exit slight right toward OR 11: Pendleton, Milton-Freewater
1496 ft · 43 sec
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26
Turn left onto Oregon-Washington Highway
1.4 km · 1 min · Oregon-Washington Highway
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27
Turn right onto Southeast Court Avenue
1.2 km · 2 min · Southeast Court Avenue
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28
Turn slight left onto New Oregon-Washington Highway
12.3 mi · 17 min · New Oregon-Washington Highway
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29
Continue on Oregon-Washington Highway
14.5 mi · 20 min · Oregon-Washington Highway
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30
Continue on South Main Street
1.2 km · 2 min · South Main Street
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31
Arrive at your destination
0 m · 1 sec · South Main Street
Car Route Details
A richer read on the saved driving route between Medford and Milton-Freewater.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
The Dalles-California Highway
Turn left onto The Dalles-California Highway
71.2 mi · 01h 29m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
Better with a longer stop
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
Partly Sunny then Chance Light Rain leaving Medford and Partly Sunny near Milton-Freewater.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Medford to Milton-Freewater?
The road trip is about 444 miles (714.6 km) and usually takes 09h 38m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
What is the halfway point on this route?
Madras is a useful midpoint, sitting about 221.8 miles from Medford and 222.2 miles from Milton-Freewater.
How much longer is the road route than the straight-line distance?
The direct path is about 334 miles (537.5 km), while the road route adds roughly 110 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 6:00 AM to 7:30 AM PDT. Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $77.58 one way or $155.16 round trip. Estimated CO2 is about 139.3 kg one way.
What should you check before leaving?
Before you leave, expect Partly Sunny then Chance Light Rain around Medford and Partly Sunny near Milton-Freewater.
Stop Ideas Near Madras
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 Madras.
Redmond Airport, Oregon
Redmond, Oregon
Sisters, OR
Bend, OR
Flight Path Map
This map shows the direct air route between Medford and Milton-Freewater. Straight-line distance: 333.97 mi (537.48 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 Milton-Freewater
City in Oregon, USA
| Population | 7,052 |
| Coordinates | 45.9326300, -118.3877400 |
| Altitude | 318 |
| Country | United States |
End: Milton-Freewater (-118.38774, 45.93263)
Estimated Travel Time
Distance: 715 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 14h 47m |
| 40 mph (64.37 km/h) | 11h 06m |
| 50 mph (80.47 km/h) | 08h 52m |
| 60 mph (96.56 km/h) | 07h 24m |
| 70 mph (112.65 km/h) | 06h 20m |
| 80 mph (129 km/h) | 05h 32m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.95 | $77.58 | $155.16 |
| Mid-grade | $5.34 | $83.65 | $167.29 |
| Premium | $5.57 | $87.22 | $174.44 |
| Diesel | $6.37 | $99.76 | $199.51 |
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 · Apr 18, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.