How far is Enterprise, OR from Medford, OR?
The driving distance from Enterprise, OR to Medford, OR is about 509.3 miles (819.6 km), with a travel time of about 10h 00m by car.
- The straight-line flight distance is about 351.4 miles (565.5 km).
- For a round trip, plan for roughly 20h 00m 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 10h 00m.
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.
Light Rain Likely
Driving Route Map
The map below follows the saved road route between Enterprise and Medford.
Turn-by-Turn Driving Directions
Step-by-step road directions between Enterprise and Medford.
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1
Start on Northwest 1st Street
20 m · 8 sec · Northwest 1st Street
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2
Turn left onto West North Street
2064 ft · 35 sec · West North Street
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3
Continue on Wallowa Lake Highway
4.8 mi · 7 min · Wallowa Lake Highway
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4
Continue on State Highway 82
4.3 mi · 6 min · State Highway 82
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5
Continue on State Street
1.4 km · 2 min · State Street
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6
Continue on East Highway 82
7.2 mi · 11 min · East Highway 82
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7
Continue on East 1st Street
2337 ft · 40 sec · East 1st Street
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8
Turn slight right onto State Highway 82
137 m · 8 sec · State Highway 82
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9
Continue on North Madison Street
614 ft · 10 sec · North Madison Street
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10
Continue on Wallowa Lake Highway
10.9 mi · 16 min · Wallowa Lake Highway
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11
Continue on State Highway 82
1.6 mi · 2 min · State Highway 82
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12
Continue on Wallowa Lake Highway
13.2 mi · 20 min · Wallowa Lake Highway
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13
Continue on Albany Street
1608 ft · 32 sec · Albany Street
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14
At the end of the road, turn left onto North 8th Avenue
2947 ft · 50 sec · North 8th Avenue
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15
Continue on State Highway 82
1873 ft · 32 sec · State Highway 82
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16
Continue on Wallowa Lake Highway
6.7 mi · 10 min · Wallowa Lake Highway
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17
Continue on Ruckman Avenue
2463 ft · 42 sec · Ruckman Avenue
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18
Continue on Wallowa Lake Highway
9.3 mi · 14 min · Wallowa Lake Highway
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19
Continue on North McAlister Road
1489 ft · 29 sec · North McAlister Road
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20
Turn right onto West 1st Street
1821 ft · 31 sec · West 1st Street
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21
Continue on Island Avenue
1.1 mi · 2 min · Island Avenue
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22
Take the ramp left
1474 ft · 36 sec
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23
Merge slight left onto Old Oregon Trail Highway
93.6 mi · 1 hr 42 min · Old Oregon Trail Highway
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24
Continue on Columbia River Highway
62.9 mi · 1 hr 7 min · Columbia River Highway
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25
Take the exit slight right toward US 97: Yakima, Bend
1274 ft · 37 sec
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26
Turn left onto Sherman Highway
55.5 mi · 1 hr 13 min · Sherman Highway
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27
Continue on E Street
2151 ft · 53 sec · E Street
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28
Turn straight onto Sherman Highway
12.3 mi · 17 min · Sherman Highway
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29
Continue on The Dalles-California Highway
24.6 mi · 29 min · The Dalles-California Highway
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30
Continue on Northeast 6th Street
1259 ft · 33 sec · Northeast 6th Street
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31
Turn left onto 4th Street
81 m · 12 sec · 4th Street
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32
Continue on Southwest 4th Street
1 mi · 3 min · Southwest 4th Street
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33
Continue on The Dalles-California Highway
26.1 mi · 38 min · The Dalles-California Highway
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34
Turn right onto Southwest Veterans Way
153 m · 14 sec · Southwest Veterans Way
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35
Turn left onto Southwest Canal Boulevard
1591 ft · 47 sec · Southwest Canal Boulevard
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36
Enter the roundabout and take exit 2 toward Southwest Canal Boulevard
18 m · 1 sec · Southwest Canal Boulevard
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37
Exit the roundabout onto Southwest Canal Boulevard
1.4 mi · 3 min · Southwest Canal Boulevard
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38
Enter the roundabout and take exit 2 toward Southwest Canal Boulevard
34 m · 2 sec · Southwest Canal Boulevard
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39
Exit the roundabout onto Southwest Canal Boulevard
1.3 km · 2 min · Southwest Canal Boulevard
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40
Enter the roundabout and take exit 2 toward Southwest Canal Boulevard
38 m · 3 sec · Southwest Canal Boulevard
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41
Exit the roundabout onto Southwest Canal Boulevard
3.8 mi · 7 min · Southwest Canal Boulevard
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42
Continue on Old Bend Redmond Highway
3.5 mi · 6 min · Old Bend Redmond Highway
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43
Enter the roundabout and take exit 2 toward Old Bend Redmond Highway
37 m · 3 sec · Old Bend Redmond Highway
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44
Exit the roundabout onto Old Bend Redmond Highway
3.1 mi · 5 min · Old Bend Redmond Highway
-
45
Enter the roundabout and take exit 3 toward McKenzie-Bend Highway
84 m · 4 sec · McKenzie-Bend Highway
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46
Exit the roundabout onto McKenzie-Bend Highway
1.2 km · 1 min · McKenzie-Bend Highway
-
47
Enter the roundabout and take exit 2 toward McKenzie-Bend Highway
40 m · 2 sec · McKenzie-Bend Highway
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48
Exit the roundabout onto McKenzie-Bend Highway
2131 ft · 36 sec · McKenzie-Bend Highway
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49
Enter the roundabout and take exit 1 toward McKenzie-Bend Highway
36 m · 2 sec · McKenzie-Bend Highway
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50
Exit the roundabout onto McKenzie-Bend Highway
1.3 km · 58 sec · McKenzie-Bend Highway
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51
Turn straight onto Northeast 3rd Street
134 m · 13 sec · Northeast 3rd Street
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52
Turn left onto Empire Avenue
821 ft · 21 sec · Empire Avenue
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53
Take the exit right
1333 ft · 33 sec
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54
Merge slight left onto Bend Parkway
5.5 mi · 9 min · Bend Parkway
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55
Continue on The Dalles-California Highway
71.1 mi · 1 hr 28 min · The Dalles-California Highway
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56
Turn right onto State Highway 138
6.3 mi · 9 min · State Highway 138
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57
Continue on East Diamond Lake Highway
8.4 mi · 12 min · East Diamond Lake Highway
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58
Continue on North Umpqua Highway
3 mi · 5 min · North Umpqua Highway
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59
Turn left onto Diamond Lake Highway
23.8 mi · 35 min · Diamond Lake Highway
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60
Continue on Crater Lake Highway
49.5 mi · 1 hr 12 min · Crater Lake Highway
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61
Turn right onto Rogue Valley Expressway
4.4 mi · 6 min · Rogue Valley Expressway
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62
Continue on Crater Lake Highway
1990 ft · 40 sec · Crater Lake Highway
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63
Turn left onto Poplar Drive
1.5 km · 2 min · Poplar Drive
-
64
Turn right onto East McAndrews Road
916 ft · 20 sec · East McAndrews Road
-
65
Turn left onto Biddle Road
156 m · 18 sec · Biddle Road
-
66
Keep slight right to continue on Biddle Road
726 ft · 14 sec · Biddle Road
-
67
Keep slight right to continue on Biddle Road
1147 ft · 22 sec · Biddle Road
-
68
Keep slight right to continue on Biddle Road
1432 ft · 29 sec · Biddle Road
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69
Continue on East 4th Street
2182 ft · 56 sec · East 4th Street
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70
Turn left onto North Fir Street
580 ft · 16 sec · North Fir Street
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71
Arrive at your destination
0 m · 1 sec · North Fir Street
Car Route Details
A richer read on the saved driving route between Enterprise and Medford.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
Old Oregon Trail Highway
Merge slight left onto Old Oregon Trail Highway
93.6 mi · 01h 42m
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.
Rain leaving Enterprise and Light Rain Likely near Medford.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Enterprise to Medford?
The road trip is about 509.3 miles (819.6 km) and usually takes 10h 00m 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?
Shaniko is a useful midpoint, sitting about 265.1 miles from Enterprise and 244.1 miles from Medford.
How much longer is the road route than the straight-line distance?
The direct path is about 351.4 miles (565.5 km), while the road route adds roughly 157.9 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 $88.97 one way or $177.94 round trip. Estimated CO2 is about 159.7 kg one way.
What should you check before leaving?
Before you leave, expect Rain around Enterprise and Light Rain Likely near Medford.
Stop Ideas Near Shaniko
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 Shaniko.
The Dalles, Oregon
Wishram
Redmond Airport, Oregon
Redmond, Oregon
Flight Path Map
This map shows the direct air route between Enterprise and Medford. Straight-line distance: 351.38 mi (565.49 km).
#1 Enterprise
City in Oregon, USA
| Population | 1,994 |
| Coordinates | 45.4262600, -117.2787800 |
| Altitude | 1144 |
| 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: 820 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 16h 58m |
| 40 mph (64.37 km/h) | 12h 43m |
| 50 mph (80.47 km/h) | 10h 11m |
| 60 mph (96.56 km/h) | 08h 29m |
| 70 mph (112.65 km/h) | 07h 16m |
| 80 mph (129 km/h) | 06h 21m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.95 | $88.97 | $177.94 |
| Mid-grade | $5.34 | $95.92 | $191.85 |
| Premium | $5.57 | $100.02 | $200.04 |
| Diesel | $6.37 | $114.40 | $228.79 |
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 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.