How far is Winchester, TN from Jackson, TN?
The driving distance from Winchester, TN to Jackson, TN is about 221 miles (355.6 km), with a travel time of about 03h 19m by car.
- The straight-line flight distance is about 155 miles (249.5 km).
- For a round trip, plan for roughly 06h 39m 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 19m.
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.
Driving Route Map
The map below follows the saved road route between Winchester and Jackson.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winchester and Jackson.
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1
Start on South Jefferson Street
23 m · 8 sec · South Jefferson Street
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2
Turn left onto 1st Avenue Southeast
51 m · 3 sec · 1st Avenue Southeast
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3
Take the exit left toward South College Street
63 m · 7 sec · South College Street
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4
Turn left onto 1st Avenue Northeast
2206 ft · 33 sec · 1st Avenue Northeast
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5
Continue on David Crockett Highway
1.1 mi · 1 min · David Crockett Highway
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6
Enter the roundabout and take exit 3 toward Rowe Gap Road
74 m · 3 sec · Rowe Gap Road
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7
Exit the roundabout onto Rowe Gap Road
1200 ft · 22 sec · Rowe Gap Road
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8
Turn right onto Veterans Memorial Drive
2594 ft · 34 sec · Veterans Memorial Drive
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9
Continue on David Crockett Highway
13.2 mi · 15 min · David Crockett Highway
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10
Continue on Winchester Highway
16.8 mi · 19 min · Winchester Highway
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11
Continue on Mulberry Avenue
2596 ft · 48 sec · Mulberry Avenue
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12
Continue on College Street East
1.2 km · 1 min · College Street East
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13
Turn slight right onto Morgan Avenue North
871 ft · 15 sec · Morgan Avenue North
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14
Continue on Washington Street West
1.3 km · 1 min · Washington Street West
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15
Continue on Pulaski Highway
31 mi · 35 min · Pulaski Highway
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16
Turn left onto West College Street
1.2 km · 50 sec · West College Street
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17
Continue on Lawrenceburg Highway
44.4 mi · 51 min · Lawrenceburg Highway
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18
Continue on Dexter L Woods Memorial Boulevard
1.2 km · 57 sec · Dexter L Woods Memorial Boulevard
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19
Turn right
12.4 mi · 14 min
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20
Turn right
30.6 mi · 35 min
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21
Turn left onto West Main Street
17.4 mi · 20 min · West Main Street
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22
Continue on West Church Sttreet
2.2 mi · 2 min · West Church Sttreet
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23
Continue straight
10.5 mi · 12 min
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24
Turn right onto Law Road
1.3 km · 1 min · Law Road
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25
Take the exit left
1042 ft · 25 sec
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26
Merge slight left
6.3 mi · 7 min
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27
Take the exit slight right toward US 70, US 412 East
684 ft · 17 sec
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28
Turn left
4.2 mi · 6 min
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29
Turn left
1.8 mi · 2 min
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30
Turn right onto East Main Street
1.1 km · 1 min · East Main Street
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31
Arrive at your destination
0 m · 1 sec · East Main Street
Car Route Details
A richer read on the saved driving route between Winchester and Jackson.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
Lawrenceburg Highway
Continue on Lawrenceburg Highway
44.4 mi · 00h 51m
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 Winchester and Sunny near Jackson.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winchester to Jackson?
The road trip is about 221 miles (355.6 km) and usually takes 03h 19m 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 Winchester and 121.8 miles from Jackson.
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 66 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 10:20 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $29.41 one way or $58.83 round trip. Estimated CO2 is about 69.3 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Winchester and Sunny near Jackson.
Flight Path Map
This map shows the direct air route between Winchester and Jackson. Straight-line distance: 155.01 mi (249.47 km).
#1 Winchester
City in Tennessee, USA
| Population | 9,097 |
| Coordinates | 35.1859200, -86.1122100 |
| Altitude | 298 |
| Country | United States |
#2 Jackson
The most populous city in Madison County, Tennessee.
| Population | 67,402 |
| Coordinates | 35.6145200, -88.8139500 |
| Altitude | 125 |
| Country | United States |
End: East Main Street (-88.813966, 35.614178)
Estimated Travel Time
Distance: 356 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 07h 21m |
| 40 mph (64.37 km/h) | 05h 31m |
| 50 mph (80.47 km/h) | 04h 25m |
| 60 mph (96.56 km/h) | 03h 40m |
| 70 mph (112.65 km/h) | 03h 09m |
| 80 mph (129 km/h) | 02h 45m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $29.41 | $58.83 |
| Mid-grade | $4.25 | $33.17 | $66.35 |
| Premium | $4.65 | $36.30 | $72.60 |
| Diesel | $5.30 | $41.37 | $82.74 |
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 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.