Oklahoma, KY to Williamsburg, KY is 229 miles and takes about 4h 33m via Cumberland Parkway and I-165, with a fuel budget near $35 and enough daylight to finish in a day. This drive stays within Kentucky, moving from the Southeast region to the Southeast region. With 92% of the route on highways, you'll experience a mostly straightforward travel day. It's a practical option if you're looking for a direct connection between these two points, with minimal fuss and a predictable duration.
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
114.5 miles from Oklahoma, KY
A natural place for your longest stop of the day
, about 2h 23m into the drive
.
Main Roads
Road
Distance
Duration
Cumberland Parkway
85.6 mi
1h 31m
I 165
39.8 mi
42m
US Route 27
26.2 mi
29m
KY 92
17.4 mi
20m
I 65
14.5 mi
15m
US Highway 231 N
10.2 mi
15m
KY 764
10.2 mi
17m
KY 914
6 mi
7m
Longest stretch:
Cumberland Parkway
— 85.6 mi, about 1h 31m
Traffic on I-65
Hour-of-day weekday pattern from 6 FHWA count stations on your route.
Peak
2 PM
~2,100 veh/hr typical
· worst 2,634
Quietest
2 AM
~357 veh/hr
Peak-to-quiet ratio
5.9×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 26 weeks of 2023 FHWA Travel Monitoring Analysis System data. Weekday hours only (Mon–Fri).
Turn-by-Turn Driving Directions
Step-by-step road directions between Oklahoma, KY and Williamsburg, KY.
1
Start on KY 764
10 mi·17 min·KY 764
2
Turn left onto KY 2115
1.1 mi·2 min·Pleasant Ridge Road
3
Turn straight onto US 231
10 mi·15 min·US Highway 231 N
4
Continue on US 231
0.2 mi·42 sec·North Main Street
5
Turn left onto KY 1543
0.2 mi·20 sec·East Union Street
Use the left lane.
6
Turn right onto KY 1543
1.1 mi·1 min·Clay Street
7
Turn left onto KY 69
0.5 mi·42 sec·KY 69
8
Take the ramp
0.4 mi·1 min
Exit 47Toward I-165 South
9
Merge onto I 165
40 mi·42 min·I 165
10
Take the exit
0.2 mi·20 sec
11
Turn left onto US 231
1.8 mi·2 min·Morgantown Road
12
Turn left onto Old Morgantown Road
1.0 mi·2 min·Old Morgantown Road
13
Turn left onto US 68 Business
361 ft·8 sec·University Boulevard
14
Continue on US 68 Business
1.6 mi·2 min·Kentucky Street
15
Continue on US 31W; US 68; KY 80
2.8 mi·4 min·Louisville Road
16
Turn right onto KY 446
0.7 mi·1 min·KY 446
17
Keep slight left at fork
0.7 mi·1 min
18
Merge onto I 65
14 mi·15 min·I 65
19
Take the exit
0.5 mi·1 min
Toward Somerset, Glasgow
20
Merge onto Cumberland Parkway
86 mi·1 hr 31 min·Cumberland Parkway
21
Take the exit
0.3 mi·32 sec
Exit 86Toward KY 914: Somerset, Burnside
22
Continue on KY 914
6.0 mi·7 min·KY 914
Use the left lane.
23
Turn right onto US 27
3.9 mi·4 min·Burnside Road
24
Continue on US 27; KY 90
26 mi·29 min·US Route 27
25
Turn left onto KY 92
17 mi·20 min·KY 92
26
Turn left onto KY 296
1.7 mi·3 min·Main Street
27
Turn right onto KY 296
256 ft·6 sec·South 5th Street
28
Turn left onto KY 296
0.2 mi·23 sec·Cumberland Avenue
29
Turn left onto South 2nd Street
427 ft·20 sec·South 2nd Street
30
Arrive at destination
North 2nd Street
Trip Plan
Given the 4h 33m estimated drive time, leaving Oklahoma, KY in the morning will get you to Williamsburg, KY well before dinner. The route has only one recommended stop, so plan to take that break strategically to stretch your legs. With the majority of the drive on highways and a fuel cost estimated at $35, you should have plenty of flexibility. Keep an eye on your fuel gauge, especially as you approach the final stretch, as highway services can sometimes be spaced out.
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 114.5 miles from Oklahoma, KY, or about 2h 23m into the drive.
The longest continuous stretch on this route runs about 85.6 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 50 miles or 1h 7m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 114.5 miles or 2h 23m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 3h 44m
Traffic, exits, and arrival timing usually matter more near Williamsburg, KY than in the middle of the route.
Before You Leave
+
Open the route before leaving Oklahoma, 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 Oklahoma, KY
This is one driving day of about 229 miles and 4h 33m.
Your first comfortable stop window is around 50 miles from Oklahoma, 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 85.6 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 21
5 decision points cluster between mile 10.2 and 228.9 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
4
10.2 mi into trip|~17m in|KY 2115 / Pleasant Ridge Road
Turn left onto KY 2115 / Pleasant Ridge Road
Navigation decision point
7
21.7 mi into trip|~35m in|KY 1543 / East Union Street
Turn left onto KY 1543 / East Union Street
Lane positioning matters here
Use the left lane.
5
87.1 mi into trip|~1h 53m in
Take the exit toward Somerset, Glasgow
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Toward Somerset, Glasgow
6
173.2 mi into trip|~3h 26m in
Take the exit toward KY 914: Somerset, Burnside
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Exit 86
Toward KY 914: Somerset, Burnside
5
228.9 mi into trip|~4h 32m in|South 2nd Street
Turn left onto South 2nd Street
Navigation decision point
Fuel & Cost
Regular Gas
$33.82 one way
$67.64 round trip
$3.75/gal25.4 MPG avg80 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.14
$37.33
$74.67
premium
$4.72
$42.52
$85.04
diesel
$4.80
$43.24
$86.48
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$34
Meals
$25–$50
Total
$59–$84
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 80.1 kg one way.
Prices: EIA weekly data, 2026-07-13.
Driving Electric?
About $24 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
68.7
0
$24.05
$10.99
Efficient EV
57.3
0
$20.04
$9.16
EV Truck/SUV
91.6
1
$32.06
$14.66
Gas CO2
80 kg
EV CO2
27 kg (66% 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 Jul 18, 2026
Origin
Oklahoma, KY
Late night
in Oklahoma on Sunday
Local time
5:41 AM
CDT
Current temp
91°F
Chance Showers And Thunderstorms
W 5 to 8 mph41% chanceLive forecast
Special Weather Statement
Special Weather Statement issued July 18 at 1:00PM CDT by NWS Louisville KY
Special Weather Statement
Special Weather Statement issued July 18 at 1:58PM EDT by NWS Louisville KY
Destination
Williamsburg, KY
Morning
in Williamsburg on Sunday
Local time
6:41 AM
EDT
Current temp
86°F
Chance Showers And Thunderstorms
W 6 mph46% chanceLive forecast
Special Weather Statement
Special Weather Statement issued July 18 at 1:00PM CDT by NWS Louisville KY
Special Weather Statement
Special Weather Statement issued July 18 at 1:58PM EDT by NWS Louisville KY
67°F
Greensburg, KY
115 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 later
The destination clock does not match departure time, so double-check hotel check-in windows and late arrival plans.
Temperature spread
5 degrees cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
4h 33m 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...
4 mi from route
~9 min detour
Free
near mile 165.8
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...
10 mi from route
~24 min detour
Free
near mile 86.9
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This drive is almost entirely on highways, with 92% of the 229 miles on high-speed roads like the Cumberland Parkway and I-165. You'll encounter your longest stretch of continuous highway driving for 85.6 miles on the Cumberland Parkway. Expect a steady pace with relatively few turns until you transition off the main highways closer to Williamsburg. The abundance of highway means frequent exits and a generally consistent driving environment.
92% highway — fuel and pacing are the main things to plan.
30 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 85.6 mi on Cumberland Parkway.
How Hard Is This Drive?
5/10
This is a straightforward highway drive that stays mostly on Cumberland Parkway and I 165. You will hit about 21 points where you need to pay attention to lane position or signs. The trickiest moment comes around 10.2 miles in near KY 2115 / Pleasant Ridge Road.
Driving Effort5/10
Moderate - straightforward overall, but long enough or busy enough to require pacing
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 229 miles you will encounter 21 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
Where does it get tricky?
The main spots that need attention: at 10.2 miles (KY 2115 / Pleasant Ridge Road): Navigation decision point; at 21.7 miles (KY 1543 / East Union Street): Lane positioning matters here; at 87.1 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Elevation Profile
Gently rolling terrain
1,297 ft435 ft
Total Climb
1,123 ft
Total Descent
632 ft
Highest Point
1,297 ft
~212.6 mi in
Elevation Range
862 ft
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Oklahoma, KY and Williamsburg, KY, road signs point toward Somerset, Glasgow and Burnside.
Oklahoma is a state in the Great Plains region of the United States of America. Oklahoma has a rich Native American past. There are all kinds of activities available from hunting, fishing, hiking, to gambling in one of the hundred or so casinos and bingo parlors, and metro activities in Tulsa and Oklahoma City
Top landmarks
•Museum of Osteology — museum in Oklahoma
•Fort Gibson — fort in Oklahoma
•Antelope Hills, Oklahoma — mountain in United States of America
Doable as a same-day drive at 4h 33m. Total distance: 229 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
4h 33m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (92%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 85.6 miles on Cumberland Parkway. The full list of main roads is in the Roads section above.
Yes — we found about 7 rest areas or service plazas within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
Yes, with realistic expectations. Build in a stop roughly every 2 hours, have snacks and activities ready, and check the Nearby Places tabs for kid-friendly stops along the way.
The main spots that need attention: at 10.2 miles (KY 2115 / Pleasant Ridge Road): Navigation decision point; at 21.7 miles (KY 1543 / East Union Street): Lane positioning matters here; at 87.1 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Yes — Mill Springs Battlefield National Monument and Mammoth Cave National Park. See the National Parks section for detour distances and tips on detours.
Possible but tiring. At 4.6 hours each way, an in-and-out day trip would put you behind the wheel for 9.1 hours — manageable with a long break at Williamsburg, KY, but most travelers stay overnight.
