How far is New York, MO from Winona, MO?
The driving distance from New York, MO to Winona, MO is about 313.9 miles (505.2 km), with a travel time of about 06h 32m by car.
- The straight-line flight distance is about 232.5 miles (374.2 km).
- For a round trip, plan for roughly 13h 05m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 7:30 AM CDT.
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 06h 32m.
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 Boone County, Missouri, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Driving Route Map
The map below follows the saved road route between New York and Winona.
Turn-by-Turn Driving Directions
Step-by-step road directions between New York and Winona.
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1
Start on the route
3.5 mi · 8 min
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2
Turn right onto Chicago-Kansas City Expressway
79.5 mi · 1 hr 32 min · Chicago-Kansas City Expressway
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3
Take the exit slight right toward US 63: Kirksville, Macon
924 ft · 25 sec
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4
Turn right onto North Missouri Street
86.2 mi · 1 hr 36 min · North Missouri Street
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5
Take the exit slight right toward US 54 West, US 63 South: Jefferson City
1.5 mi · 2 min
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6
Take the exit slight right toward US 63 South, US 50
66 m · 5 sec
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7
Keep slight left to continue on US 63 South, US 50
724 ft · 16 sec
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8
Keep slight left to continue on US 63 South, US 50 East
547 ft · 15 sec
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9
Keep slight left
12 mi · 15 min
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10
Keep slight right to continue on US 63 South: Rolla
49.4 mi · 1 hr 4 min
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11
Turn left onto North Walnut Street
747 ft · 26 sec · North Walnut Street
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12
Continue on East 18th Street
1072 ft · 39 sec · East 18th Street
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13
Turn right onto Holloway Street
1.4 km · 3 min · Holloway Street
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14
At the end of the road, turn left onto Salem Avenue
1.2 km · 2 min · Salem Avenue
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15
Turn left
2.3 mi · 4 min
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16
Continue straight
22 mi · 28 min
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17
At the end of the road, turn left
1.5 mi · 3 min
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18
Turn right onto South Main Street
53.7 mi · 1 hr 15 min · South Main Street
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19
Turn left
23 m · 2 sec
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20
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between New York and Winona.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
North Missouri Street
Turn right onto North Missouri Street
86.2 mi · 01h 36m
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.
Sunny leaving New York and Sunny near Winona.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from New York to Winona?
The road trip is about 313.9 miles (505.2 km) and usually takes 06h 32m 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?
Ashland is a useful midpoint, sitting about 157 miles from New York and 157 miles from Winona.
How much longer is the road route than the straight-line distance?
The direct path is about 232.5 miles (374.2 km), while the road route adds roughly 81.4 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 6:00 AM to 7:30 AM CDT. 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 $41.78 one way or $83.57 round trip. Estimated CO2 is about 98.5 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around New York and Sunny near Winona.
Stop Ideas Near Ashland
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 Ashland.
Jefferson City
Hermann
Sedalia
Washington
Flight Path Map
This map shows the direct air route between New York and Winona. Straight-line distance: 232.52 mi (374.2 km).
#1 New York
Human settlement in Missouri, United States of America
| Population | 264 |
| Coordinates | 39.6852900, -93.9268800 |
| Altitude | 244 |
| Country | United States |
#2 Winona
City in Missouri, United States
| Population | 1,296 |
| Coordinates | 37.0097700, -91.3234700 |
| Altitude | 284 |
| Country | United States |
End: Winona (-91.32347, 37.00977)
Estimated Travel Time
Distance: 505 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 10h 27m |
| 40 mph (64.37 km/h) | 07h 50m |
| 50 mph (80.47 km/h) | 06h 16m |
| 60 mph (96.56 km/h) | 05h 13m |
| 70 mph (112.65 km/h) | 04h 29m |
| 80 mph (129 km/h) | 03h 54m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $41.78 | $83.57 |
| Mid-grade | $4.25 | $47.12 | $94.25 |
| Premium | $4.65 | $51.57 | $103.13 |
| Diesel | $5.30 | $58.77 | $117.54 |
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 Missouri · Jun 29, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.