How far is Windsor, WI from Rutland, WI?
The driving distance from Windsor, WI to Rutland, WI is about 30.9 miles (49.8 km), with a travel time of about 00h 39m by car.
- The straight-line flight distance is about 23.5 miles (37.8 km).
- For a round trip, plan for roughly 01h 19m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 7:00 AM to 7:00 PM CDT.
Reverse, save, or send this route
This is an easy same-day return drive. Copy the route link, send it to another device, or print a clean version before you head out.
This is an easy same-day return drive.
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 00h 39m.
This is a short drive, so your comfort window is wide. Traffic and current weather matter more than the clock.
This departure sits inside the recommended comfort window for the route.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
City in Dane County, Wisconsin, United States of America
Route Weather Snapshot
Check the forecast at both ends before you head out.
Rain Showers
Rain Showers
Driving Route Map
The map below follows the saved road route between Windsor and Rutland.
Turn-by-Turn Driving Directions
Step-by-step road directions between Windsor and Rutland.
-
1
Start on 2nd Street
149 m · 27 sec · 2nd Street
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2
Turn left onto Lake Road
1.6 mi · 3 min · Lake Road
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3
Turn straight
63 m · 10 sec
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4
Turn slight right onto State Highway 19
840 ft · 24 sec · State Highway 19
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5
Turn left onto I 39 South, I 90 East, I 94 East: Madison
2565 ft · 1 min
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6
Merge slight left
6.3 mi · 7 min
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7
Keep slight right to continue on I 39, I 90: Chicago
3.8 mi · 4 min
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8
Take the exit slight right toward US 12 West, US 18 West: Madison
1.4 km · 1 min
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9
Merge slight left onto South Beltline Highway
5.3 mi · 7 min · South Beltline Highway
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10
Take the exit slight right toward US 151 North, US 14 East: Park Street, Oregon
1278 ft · 31 sec
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11
Keep slight left to continue on US 18 Alternate West, US 151 Alternate South, US 14 East: Fitchburg, Oregon
43 m · 5 sec
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12
Turn left onto South Park Street
11.9 mi · 14 min · South Park Street
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13
Turn left onto Old Stage Road
134 m · 11 sec · Old Stage Road
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14
Turn right
54 m · 13 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 Windsor and Rutland.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
South Park Street
Turn left onto South Park Street
11.9 mi · 00h 14m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A short regional drive
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
Rain Showers leaving Windsor and Rain Showers near Rutland.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Windsor to Rutland?
The road trip is about 30.9 miles (49.8 km) and usually takes 00h 39m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
What is the halfway point on this route?
Monona is a useful midpoint, sitting about 15.5 miles from Windsor and 15.5 miles from Rutland.
How much longer is the road route than the straight-line distance?
The direct path is about 23.5 miles (37.8 km), while the road route adds roughly 7.4 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 7:00 AM to 7:00 PM CDT. If you want a more comfortable same-day return, try to leave by 7:10 PM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $4.49 one way or $8.97 round trip. Estimated CO2 is about 9.7 kg one way.
What should you check before leaving?
Before you leave, expect Rain Showers around Windsor and Rain Showers near Rutland.
Stop Ideas Near Monona
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 Monona.
Madison (South), Wisconsin
Madison, Wisconsin
Columbus
Janesville, Wisconsin
Flight Path Map
This map shows the direct air route between Windsor and Rutland. Straight-line distance: 23.46 mi (37.75 km).
#1 Windsor
Village in Dane County, Wisconsin , United States
| Population | 7,810 |
| Coordinates | 43.2183300, -89.3415100 |
| Altitude | 274 |
| Country | United States |
#2 Rutland
Town in Dane County, Wisconsin, United States
| Population | 2,090 |
| Coordinates | 42.8788900, -89.3501200 |
| Altitude | 288 |
| Country | United States |
End: Rutland (-89.35012, 42.87889)
Estimated Travel Time
Distance: 50 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 01m |
| 40 mph (64.37 km/h) | 00h 46m |
| 50 mph (80.47 km/h) | 00h 37m |
| 60 mph (96.56 km/h) | 00h 30m |
| 70 mph (112.65 km/h) | 00h 26m |
| 80 mph (129 km/h) | 00h 23m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.12 | $4.49 | $8.97 |
| Mid-grade | $4.72 | $5.14 | $10.28 |
| Premium | $5.30 | $5.77 | $11.55 |
| Diesel | $6.19 | $6.75 | $13.50 |
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 Wisconsin · Oct 15, 2026