How far is Milton-Freewater, OR from Medford, OR?
The driving distance from Milton-Freewater, OR to Medford, OR is about 444.9 miles (716 km), with a travel time of about 08h 07m by car.
- The straight-line flight distance is about 334 miles (537.5 km).
- For a round trip, plan for roughly 16h 14m 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 08h 07m.
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.
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Milton-Freewater and Medford.
Turn-by-Turn Driving Directions
Step-by-step road directions between Milton-Freewater and Medford.
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1
Start on South Main Street
1.2 km · 2 min · South Main Street
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2
Turn straight onto Oregon-Washington Highway
14.5 mi · 20 min · Oregon-Washington Highway
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3
Continue on New Oregon-Washington Highway
12.3 mi · 17 min · New Oregon-Washington Highway
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4
Keep slight left to continue on New Oregon-Washington Highway
69 m · 4 sec · New Oregon-Washington Highway
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5
Continue on Southeast Court Avenue
1.2 km · 2 min · Southeast Court Avenue
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6
Turn left onto Oregon-Washington Highway
1.2 km · 1 min · Oregon-Washington Highway
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7
Take the ramp right
1726 ft · 42 sec
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8
Merge slight left onto Old Oregon Trail Highway
43 mi · 47 min · Old Oregon Trail Highway
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9
Continue on Columbia River Highway
62.9 mi · 1 hr 7 min · Columbia River Highway
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10
Take the exit slight right toward US 97: Yakima, Bend
1274 ft · 37 sec
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11
Turn left onto Sherman Highway
55.5 mi · 1 hr 13 min · Sherman Highway
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12
Continue on E Street
2151 ft · 53 sec · E Street
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13
Turn straight onto Sherman Highway
12.3 mi · 17 min · Sherman Highway
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14
Continue on The Dalles-California Highway
24.6 mi · 29 min · The Dalles-California Highway
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15
Continue on Northeast 6th Street
1259 ft · 33 sec · Northeast 6th Street
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16
Turn left onto 4th Street
81 m · 12 sec · 4th Street
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17
Continue on Southwest 4th Street
1 mi · 3 min · Southwest 4th Street
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18
Continue on The Dalles-California Highway
26.1 mi · 38 min · The Dalles-California Highway
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19
Turn right onto Southwest Veterans Way
153 m · 14 sec · Southwest Veterans Way
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20
Turn left onto Southwest Canal Boulevard
1591 ft · 47 sec · Southwest Canal Boulevard
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21
Enter the roundabout and take exit 2 toward Southwest Canal Boulevard
18 m · 1 sec · Southwest Canal Boulevard
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22
Exit the roundabout onto Southwest Canal Boulevard
1.4 mi · 3 min · Southwest Canal Boulevard
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23
Enter the roundabout and take exit 2 toward Southwest Canal Boulevard
34 m · 2 sec · Southwest Canal Boulevard
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24
Exit the roundabout onto Southwest Canal Boulevard
1.3 km · 2 min · Southwest Canal Boulevard
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25
Enter the roundabout and take exit 2 toward Southwest Canal Boulevard
38 m · 3 sec · Southwest Canal Boulevard
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26
Exit the roundabout onto Southwest Canal Boulevard
3.8 mi · 7 min · Southwest Canal Boulevard
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27
Continue on Old Bend Redmond Highway
3.5 mi · 6 min · Old Bend Redmond Highway
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28
Enter the roundabout and take exit 2 toward Old Bend Redmond Highway
37 m · 3 sec · Old Bend Redmond Highway
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29
Exit the roundabout onto Old Bend Redmond Highway
3.1 mi · 5 min · Old Bend Redmond Highway
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30
Enter the roundabout and take exit 3 toward McKenzie-Bend Highway
84 m · 4 sec · McKenzie-Bend Highway
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31
Exit the roundabout onto McKenzie-Bend Highway
1.2 km · 1 min · McKenzie-Bend Highway
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32
Enter the roundabout and take exit 2 toward McKenzie-Bend Highway
40 m · 2 sec · McKenzie-Bend Highway
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33
Exit the roundabout onto McKenzie-Bend Highway
2131 ft · 36 sec · McKenzie-Bend Highway
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34
Enter the roundabout and take exit 1 toward McKenzie-Bend Highway
36 m · 2 sec · McKenzie-Bend Highway
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35
Exit the roundabout onto McKenzie-Bend Highway
1.3 km · 58 sec · McKenzie-Bend Highway
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36
Turn straight onto Northeast 3rd Street
134 m · 13 sec · Northeast 3rd Street
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37
Turn left onto Empire Avenue
821 ft · 21 sec · Empire Avenue
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38
Take the exit right
1333 ft · 33 sec
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39
Merge slight left onto Bend Parkway
5.5 mi · 9 min · Bend Parkway
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40
Continue on The Dalles-California Highway
71.1 mi · 1 hr 28 min · The Dalles-California Highway
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41
Turn right onto State Highway 138
6.3 mi · 9 min · State Highway 138
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42
Continue on East Diamond Lake Highway
8.4 mi · 12 min · East Diamond Lake Highway
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43
Continue on North Umpqua Highway
3 mi · 5 min · North Umpqua Highway
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44
Turn left onto Diamond Lake Highway
23.8 mi · 35 min · Diamond Lake Highway
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45
Continue on Crater Lake Highway
49.5 mi · 1 hr 12 min · Crater Lake Highway
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46
Turn right onto Rogue Valley Expressway
4.4 mi · 6 min · Rogue Valley Expressway
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47
Continue on Crater Lake Highway
1990 ft · 40 sec · Crater Lake Highway
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48
Turn left onto Poplar Drive
1.5 km · 2 min · Poplar Drive
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49
Turn right onto East McAndrews Road
916 ft · 20 sec · East McAndrews Road
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50
Turn left onto Biddle Road
156 m · 18 sec · Biddle Road
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51
Keep slight right to continue on Biddle Road
726 ft · 14 sec · Biddle Road
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52
Keep slight right to continue on Biddle Road
1147 ft · 22 sec · Biddle Road
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53
Keep slight right to continue on Biddle Road
1432 ft · 29 sec · Biddle Road
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54
Continue on East 4th Street
2182 ft · 56 sec · East 4th Street
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55
Turn left onto North Fir Street
580 ft · 16 sec · North Fir Street
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56
Arrive at your destination
0 m · 1 sec · North Fir Street
Car Route Details
A richer read on the saved driving route between Milton-Freewater and Medford.
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
Continue on The Dalles-California Highway
71.1 mi · 01h 28m
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.
Mostly Sunny leaving Milton-Freewater and Sunny near Medford.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Milton-Freewater to Medford?
The road trip is about 444.9 miles (716 km) and usually takes 08h 07m 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 222.8 miles from Milton-Freewater and 222.1 miles from Medford.
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 110.9 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 $77.73 one way or $155.46 round trip. Estimated CO2 is about 139.5 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Milton-Freewater and Sunny near Medford.
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 Milton-Freewater and Medford. Straight-line distance: 333.97 mi (537.48 km).
#1 Milton-Freewater
City in Oregon, USA
| Population | 7,052 |
| Coordinates | 45.9326300, -118.3877400 |
| Altitude | 318 |
| 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: 716 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 14h 49m |
| 40 mph (64.37 km/h) | 11h 07m |
| 50 mph (80.47 km/h) | 08h 53m |
| 60 mph (96.56 km/h) | 07h 24m |
| 70 mph (112.65 km/h) | 06h 21m |
| 80 mph (129 km/h) | 05h 33m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.95 | $77.73 | $155.46 |
| Mid-grade | $5.34 | $83.81 | $167.61 |
| Premium | $5.57 | $87.39 | $174.77 |
| Diesel | $6.37 | $99.95 | $199.89 |
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.