This 264.5-mile drive from Williamsburg to Henderson, Kentucky, is a straightforward, highway-focused journey that can comfortably be completed in about 5 hours. With 93% of the route on main roads, it's an efficient way to travel across the state. The estimated fuel cost is around $41, making it an economical option for a day trip, though you'll want to plan for one stop along the way. This drive stays within the Southeast region of Kentucky, offering a consistent feel throughout. It's a practical choice if you're looking for a direct route with minimal fuss.
Trip Pace
Same-day drive is realistic
A same-day return is possible, but it will make for a full day on the road.
Break Rhythm
1 planned break
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
132.3 miles from Williamsburg, KY
A natural place for your longest stop of the day
, about 2h 29m into the drive
.
Main Roads
Road
Distance
Duration
Cumberland Parkway
86.2 mi
1h 32m
I 165
62.3 mi
1h 6m
US Route 27
26.2 mi
29m
Audubon Parkway
23.2 mi
24m
KY 92
17.4 mi
20m
I 65
16.5 mi
17m
Wendell Ford Expressway
6.3 mi
7m
KY 914
6 mi
7m
Longest stretch:
Cumberland Parkway
— 86.2 mi, about 1h 32m
Turn-by-Turn Driving Directions
Step-by-step road directions between Williamsburg, KY and Henderson, KY.
1
Start on North 2nd Street
137 ft·10 sec·North 2nd Street
2
Turn right onto KY 296
1.9 mi·3 min·Main Street
3
Turn right onto KY 92
17 mi·20 min·KY 92
4
At end of road, turn right onto US 27; KY 92
26 mi·29 min·US Route 27
5
Continue on US 27; KY 90
3.9 mi·4 min·Main Street
6
Turn left onto KY 914
6.0 mi·7 min·KY 914
7
Keep slight left at fork
0.6 mi·1 min
Toward Bowling Green
8
Merge onto Cumberland Parkway
86 mi·1 hr 32 min·Cumberland Parkway
9
Continue on Cumberland Parkway
0.3 mi·19 sec·Cumberland Parkway
Exit 1BToward I 65 South: Bowling Green
10
Continue on Cumberland Expressway
0.7 mi·1 min·Cumberland Expressway
11
Merge onto I 65
17 mi·17 min·I 65
12
Take the exit
0.2 mi·35 sec
Toward KY 234: Bowling Green
13
Turn right onto KY 234
1.0 mi·1 min·Cemetery Road
14
Continue on KY 234
1.6 mi·2 min·Fairview Avenue
15
Continue on KY 234
0.8 mi·1 min·East 6th Avenue
16
Continue on US 68; KY 80
3.7 mi·5 min·Veterans Memorial Lane
17
Turn right onto US 231
1.0 mi·1 min·Morgantown Road
18
Take the ramp
0.3 mi·33 sec
19
Merge onto I 165
62 mi·1 hr 6 min·I 165
20
Keep slight left at fork
0.7 mi·1 min
Exit 70BToward US 60 West, US 231 South: Henderson
21
Merge onto US 60; US 231
6.3 mi·7 min·Wendell Ford Expressway
22
Take the exit
0.4 mi·57 sec
Exit 10Toward Audubon Parkway West: Henderson
23
Continue on Audubon Parkway
23 mi·24 min·Audubon Parkway
24
Take the exit
0.4 mi·1 min
Exit 1AToward US 41 North: Henderson
25
Merge onto I 69; US41
1.0 mi·1 min·I 69; US41
26
Take the exit
0.2 mi·48 sec
Exit 14Toward KY 351: Zion, Henderson
27
Turn slight right onto KY 351
1.4 mi·2 min·2nd Street
28
Turn left onto US 60; US 41 Alt
0.3 mi·42 sec·North Green Street
29
Turn left onto Washington Street
213 ft·10 sec·Washington Street
30
Turn left
98 ft·7 sec
31
Arrive at destination
Trip Plan
For this 5-hour, 264.5-mile trip, starting early in the morning will give you ample daylight and allow you to reach Henderson without feeling rushed. With only one recommended stop, you can easily manage your breaks, perhaps planning it around the 86.2-mile stretch on the Cumberland Parkway. Keep an eye on your fuel gauge, especially before heading out, as the estimated cost is $41 and you want to avoid unnecessary detours for gas. Since this is a manageable one-day drive, you have the flexibility to depart when it suits you best.
Morning Departure
An early start around 7-8 AM gets you there with plenty of daylight left.
Evening Departure
A late afternoon start means arriving after dark. Morning is better.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 132.3 miles from Williamsburg, KY, or about 2h 29m into the drive.
The longest continuous stretch on this route runs about 86.2 miles.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 58 miles or 1h 9m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 132.3 miles or 2h 29m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 4h 4m
Traffic, exits, and arrival timing usually matter more near Henderson, KY than in the middle of the route.
Before You Leave
+
Open the route before leaving Williamsburg, KY so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Williamsburg, KY
This is one driving day of about 264.5 miles and 5h.
Your first comfortable stop window is around 58 miles from Williamsburg, KY.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 1 real break rather than only quick fuel stops.
The longest stretch is on Cumberland Parkway for about 86.2 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 20
5 decision points cluster between mile 55.5 and 262.6 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
55.5 mi into trip|~1h 5m in
Keep slight left at fork toward Bowling Green
Highway fork - watch signs carefully
Toward Bowling Green
7
230.5 mi into trip|~4h 19m in
Keep slight left at fork toward US 60 West, US 231 South: Henderson
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Exit 70B
Toward US 60 West, US 231 South: Henderson
5
237.4 mi into trip|~4h 28m in
Take the exit toward Audubon Parkway West: Henderson
Exit ramp - move to the correct lane early
Exit 10
Toward Audubon Parkway West: Henderson
5
261.1 mi into trip|~4h 54m in
Take the exit toward US 41 North: Henderson
Exit ramp - move to the correct lane early
Exit 1A
Toward US 41 North: Henderson
6
262.6 mi into trip|~4h 56m in
Take the exit toward KY 351: Zion, Henderson
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Exit 14
Toward KY 351: Zion, Henderson
Fuel & Cost
Regular Gas
$41.35 one way
$82.70 round trip
$3.97/gal25.4 MPG avg93 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.36
$45.40
$90.80
premium
$4.89
$50.90
$101.80
diesel
$5.61
$58.40
$116.80
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$41
Meals
$25–$50
Total
$66–$91
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 92.5 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $28 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
79.4
0
$27.77
$12.70
Efficient EV
66.1
0
$23.14
$10.58
EV Truck/SUV
105.8
1
$37.03
$16.93
Gas CO2
93 kg
EV CO2
31 kg (67% less)
Plan for 0 charging stops, roughly every 270 miles. Allow 25-40 minutes per stop at a DC fast charger.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive.
Forecast as of Apr 18, 2026
Origin
Williamsburg, KY
Late night
in Williamsburg on Sunday
Local time
2:03 AM
EDT
Current temp
56°F
Partly Cloudy
SSE 1 mph1% chanceLive forecast
Destination
Henderson, KY
Late night
in Henderson on Sunday
Local time
1:03 AM
CDT
Current temp
56°F
Chance Showers And Thunderstorms
SW 10 mph64% chanceLive forecast
75°F
Glasgow, KY
132 mi in
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
1 hour earlier
The destination clock does not match departure time, so double-check hotel check-in windows and late arrival plans.
Temperature spread
Very similar conditions
Both ends of the route are sitting at about the same temperature right now.
Road read
5h on the road
An early start around 7-8 AM gets you there with plenty of daylight left.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
National Parks Near This Route
Worth a detour if your schedule allows.
Mill Springs Battlefield National Monument
National Monument
The US won a significant victory early in the Civil War at the Battle of Mill Springs. Explore the rolling fields of Kentucky where the battle took place and learn about that state's strategic importa...
Rolling hills, deep river valleys, and the world's longest known cave system. Mammoth Cave National Park is home to thousands of years of human history and a rich diversity of plant and animal life, e...
11 mi from route
~27 min detour
Free
near mile 145.9
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a predominantly highway experience on this 5-hour drive, with 93% of the miles covered on main roads. You'll spend a significant portion of your time on the Cumberland Parkway, including the longest uninterrupted stretch of 86.2 miles. The route transitions to I-165 and US Route 27, maintaining a focus on efficient travel. While primarily highway, the shift between these main arteries offers a slight change in scenery and road feel without deviating from the direct path. It’s a drive built for covering distance.
93% highway — fuel and pacing are the main things to plan.
31 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 86.2 mi on Cumberland Parkway.
How Hard Is This Drive?
7/10
This is a straightforward highway drive that stays mostly on Cumberland Parkway and I 165. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 55.5 miles in.
Driving Effort7/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This is a demanding drive. With 20 significant decision points across 264.5 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 55.5 miles: Highway fork - watch signs carefully; at 230.5 miles: Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 237.4 miles: Exit ramp - move to the correct lane early.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Williamsburg, KY and Henderson, KY, road signs point toward Bowling Green and Audubon Parkway West: Henderson.
Doable as a same-day drive at 5h. Total distance: 264.5 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (93%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 86.2 miles on Cumberland Parkway. The full list of main roads is in the Roads section above.
We did not find dedicated rest areas on this route. For a drive this long, plan bathroom and stretch breaks around gas stations, fast-food stops, or small-town downtowns — check the Nearby Places section for options.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Henderson, KY before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 1 meaningful breaks. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 55.5 miles: Highway fork - watch signs carefully; at 230.5 miles: Highway fork - watch signs carefully. Multiple destination signs - pick the right one; at 237.4 miles: Exit ramp - move to the correct lane early.
Yes — Mill Springs Battlefield National Monument and Mammoth Cave National Park. See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 5.0 hours each way, a round trip means 10.0 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Henderson, KY before the return drive.
