How far is Winston, OR from Gresham, OR?
The driving distance from Winston, OR to Gresham, OR is about 197.4 miles (317.7 km), with a travel time of about 03h 20m by car.
- The straight-line flight distance is about 171.2 miles (275.5 km).
- For a round trip, plan for roughly 06h 40m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 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 03h 20m.
An early departure helps you fit a real stop into the day without turning the return into a late-night drive.
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
Light Rain
Driving Route Map
The map below follows the saved road route between Winston and Gresham.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winston and Gresham.
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1
Start on North Main Street
2582 ft · 44 sec · North Main Street
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2
Continue on Coos Bay-Roseburg Highway
2.7 mi · 4 min · Coos Bay-Roseburg Highway
-
3
Take the ramp straight
3179 ft · 1 min
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4
Merge slight left
168.2 mi · 3 hr 16 min
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5
Take the exit slight right toward I 205 North: Oregon City
1.2 km · 53 sec
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6
Continue straight
16.4 mi · 21 min
-
7
Take the exit slight right toward Foster Road
1473 ft · 42 sec
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8
Turn right onto Southeast Woodstock Boulevard
873 ft · 25 sec · Southeast Woodstock Boulevard
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9
Turn slight right onto Southeast Foster Road
3.3 mi · 7 min · Southeast Foster Road
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10
Turn left onto Southeast Jenne Road
1.5 km · 2 min · Southeast Jenne Road
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11
Continue on Southeast 174th Avenue
2520 ft · 1 min · Southeast 174th Avenue
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12
Turn right onto Southeast Powell Boulevard
732 ft · 21 sec · Southeast Powell Boulevard
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13
Continue on West Powell Boulevard
2.7 mi · 6 min · West Powell Boulevard
-
14
Turn left
36 m · 9 sec
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15
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Winston and Gresham.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Coos Bay-Roseburg Highway
Merge slight left
168 mi · 03h 16m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A longer out-and-back drive
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
Light Rain leaving Winston and Light Rain near Gresham.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winston to Gresham?
The road trip is about 197.4 miles (317.7 km) and usually takes 03h 20m in normal driving conditions.
Is this a same-day trip or an overnight route?
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
What is the halfway point on this route?
Halsey is a useful midpoint, sitting about 98.5 miles from Winston and 98.9 miles from Gresham.
How much longer is the road route than the straight-line distance?
The direct path is about 171.2 miles (275.5 km), while the road route adds roughly 26.2 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 8:00 AM PDT. If you want a more comfortable same-day return, try to leave by 10:20 AM PDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $34.51 one way or $69.02 round trip. Estimated CO2 is about 61.9 kg one way.
What should you check before leaving?
Before you leave, expect Light Rain around Winston and Light Rain near Gresham.
Stop Ideas Near Halsey
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 Halsey.
Corvallis, Oregon
Albany station
Eugene–Springfield
Eugene, OR
Flight Path Map
This map shows the direct air route between Winston and Gresham. Straight-line distance: 171.17 mi (275.47 km).
#1 Winston
City in Oregon, USA
| Population | 5,541 |
| Coordinates | 43.1223400, -123.4125700 |
| Altitude | 169 |
| Country | United States |
#2 Gresham
The second most populous city in Multnomah County, Oregon.
| Population | 110,031 |
| Coordinates | 45.4981800, -122.4314800 |
| Altitude | 97 |
| Country | United States |
End: (-122.431495, 45.498179)
Estimated Travel Time
Distance: 318 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 06h 34m |
| 40 mph (64.37 km/h) | 04h 56m |
| 50 mph (80.47 km/h) | 03h 56m |
| 60 mph (96.56 km/h) | 03h 17m |
| 70 mph (112.65 km/h) | 02h 49m |
| 80 mph (129 km/h) | 02h 27m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.95 | $34.51 | $69.02 |
| Mid-grade | $5.34 | $37.21 | $74.41 |
| Premium | $5.57 | $38.80 | $77.59 |
| Diesel | $6.37 | $44.37 | $88.74 |
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.