How far is Jackson, TN from Winchester, TN?
The driving distance from Jackson, TN to Winchester, TN is about 198.5 miles (319.4 km), with a travel time of about 03h 50m by car.
- The straight-line flight distance is about 155 miles (249.5 km).
- For a round trip, plan for roughly 07h 40m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 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 03h 50m.
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 Tennessee
Route Weather Snapshot
Check the forecast at both ends before you head out.
Sunny
Driving Route Map
The map below follows the saved road route between Jackson and Winchester.
Turn-by-Turn Driving Directions
Step-by-step road directions between Jackson and Winchester.
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1
Start on East Main Street
1.1 km · 1 min · East Main Street
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2
At the end of the road, turn left
1.8 mi · 2 min
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3
Turn right onto Whitehall Street
4 mi · 6 min · Whitehall Street
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4
Take the ramp slight right
1308 ft · 32 sec
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5
Merge slight left
6.3 mi · 7 min
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6
Take the exit slight right toward 152: Lexington
919 ft · 23 sec
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7
Turn right onto Law Road
1.2 km · 50 sec · Law Road
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8
Turn left
10.4 mi · 12 min
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9
Turn left
7.5 mi · 9 min
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10
Continue on US 412;SR 114
3.5 mi · 4 min · US 412;SR 114
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11
Merge slight left
8.8 mi · 10 min
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12
Turn right onto South Tennessee Avenue
25.1 mi · 29 min · South Tennessee Avenue
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13
Continue on Billy Nance Highway West
1.1 mi · 1 min · Billy Nance Highway West
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14
Continue on Billy Nance Road
4.4 mi · 5 min · Billy Nance Road
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15
At the end of the road, turn left onto Savannah Highway
12.4 mi · 15 min · Savannah Highway
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16
Continue on Dexter L Woods Memorial Boulevard
1.2 km · 53 sec · Dexter L Woods Memorial Boulevard
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17
Continue on United States Route 64
44.4 mi · 51 min · United States Route 64
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18
Continue on West College Street
1.2 km · 49 sec · West College Street
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19
Continue straight
63.7 mi · 1 hr 14 min
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20
Turn left onto Rowe Gap Road
1264 ft · 21 sec · Rowe Gap Road
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21
Enter the roundabout and take exit 1 toward David Crockett Highway
11 m · 1 sec · David Crockett Highway
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22
Exit the roundabout onto David Crockett Highway
1.1 mi · 1 min · David Crockett Highway
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23
Turn slight right onto 1st Avenue Southwest
2071 ft · 29 sec · 1st Avenue Southwest
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24
Take the exit left toward South College Street
63 m · 7 sec · South College Street
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25
Turn left onto 1st Avenue Northeast
56 m · 6 sec · 1st Avenue Northeast
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26
Turn left onto South Jefferson Street
58 m · 5 sec · South Jefferson Street
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27
Arrive at your destination
0 m · 1 sec · South Jefferson Street
Car Route Details
A richer read on the saved driving route between Jackson and Winchester.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
West College Street
Continue straight
63.7 mi · 01h 14m
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.
Sunny leaving Jackson and Sunny near Winchester.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Jackson to Winchester?
The road trip is about 198.5 miles (319.4 km) and usually takes 03h 50m 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?
Waynesboro is a useful midpoint, sitting about 99.2 miles from Jackson and 99.3 miles from Winchester.
How much longer is the road route than the straight-line distance?
The direct path is about 155 miles (249.5 km), while the road route adds roughly 43.5 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 CDT. If you want a more comfortable same-day return, try to leave by 9:20 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $26.40 one way or $52.79 round trip. Estimated CO2 is about 62.2 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Jackson and Sunny near Winchester.
Flight Path Map
This map shows the direct air route between Jackson and Winchester. Straight-line distance: 155.01 mi (249.47 km).
#1 Jackson
The most populous city in Madison County, Tennessee.
| Population | 67,402 |
| Coordinates | 35.6145200, -88.8139500 |
| Altitude | 125 |
| Country | United States |
#2 Winchester
City in Tennessee, USA
| Population | 9,097 |
| Coordinates | 35.1859200, -86.1122100 |
| Altitude | 298 |
| Country | United States |
End: Winchester (-86.11221, 35.18592)
Estimated Travel Time
Distance: 319 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 06h 36m |
| 40 mph (64.37 km/h) | 04h 57m |
| 50 mph (80.47 km/h) | 03h 58m |
| 60 mph (96.56 km/h) | 03h 18m |
| 70 mph (112.65 km/h) | 02h 50m |
| 80 mph (129 km/h) | 02h 28m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $26.40 | $52.79 |
| Mid-grade | $4.25 | $29.77 | $59.54 |
| Premium | $4.65 | $32.58 | $65.16 |
| Diesel | $5.30 | $37.13 | $74.26 |
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 Tennessee · May 04, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.