How far is Leonardtown, MD from Gwynn Oak, MD?
The driving distance from Leonardtown, MD to Gwynn Oak, MD is about 96 miles (154.5 km), with a travel time of about 01h 56m by car.
- The straight-line flight distance is about 72 miles (115.9 km).
- For a round trip, plan for roughly 03h 53m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
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 01h 56m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
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.
Town in Maryland, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Showers And Thunderstorms
Rain Showers
Driving Route Map
The map below follows the saved road route between Leonardtown and Gwynn Oak.
Turn-by-Turn Driving Directions
Step-by-step road directions between Leonardtown and Gwynn Oak.
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1
Start on Fenwick Street
14 m · 7 sec · Fenwick Street
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2
Turn left onto Washington Street
2131 ft · 50 sec · Washington Street
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3
Turn left onto Point Lookout Road
11.7 mi · 19 min · Point Lookout Road
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4
Take the ramp straight
126 m · 11 sec
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5
Merge slight right onto Three Notch Road
6.9 mi · 10 min · Three Notch Road
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6
Continue on Leonardtown Road
10.6 mi · 15 min · Leonardtown Road
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7
Turn right onto Mattawoman Beantown Road
3.3 mi · 5 min · Mattawoman Beantown Road
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8
Merge slight left onto Crain Highway
2.5 mi · 4 min · Crain Highway
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9
Keep slight right to continue on Crain Highway
13 mi · 18 min · Crain Highway
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10
Continue on South East Crain Highway
10.8 mi · 16 min · South East Crain Highway
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11
Continue on Robert Crain Highway
7.1 mi · 11 min · Robert Crain Highway
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12
Merge slight left
8.9 mi · 10 min
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13
Take the exit slight right toward I 695 West: Baltimore, Towson
1.1 mi · 1 min
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14
Merge slight right onto Baltimore Beltway
7.7 mi · 10 min · Baltimore Beltway
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15
Take the exit slight right toward US 40 East: Baltimore
1820 ft · 44 sec
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16
Turn straight onto Baltimore National Pike
957 ft · 22 sec · Baltimore National Pike
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17
Turn left onto Ingleside Avenue
1.6 mi · 3 min · Ingleside Avenue
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18
Continue on North Forest Park Avenue
1.4 mi · 4 min · North Forest Park Avenue
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19
Turn slight left onto Hillsdale Road
1.5 km · 3 min · Hillsdale Road
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20
Turn right onto Haddon Avenue
54 m · 11 sec · Haddon Avenue
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21
Turn left
18 m · 4 sec
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22
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Leonardtown and Gwynn Oak.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
Crain Highway
Keep slight right to continue on Crain Highway
13 mi · 00h 18m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Showers And Thunderstorms leaving Leonardtown and Rain Showers near Gwynn Oak.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Leonardtown to Gwynn Oak?
The road trip is about 96 miles (154.5 km) and usually takes 01h 56m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Upper Marlboro is a useful midpoint, sitting about 44.3 miles from Leonardtown and 51.7 miles from Gwynn Oak.
How much longer is the road route than the straight-line distance?
The direct path is about 72 miles (115.9 km), while the road route adds roughly 24 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 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 2:36 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $13.85 one way or $27.70 round trip. Estimated CO2 is about 30.1 kg one way.
What should you check before leaving?
Before you leave, expect Showers And Thunderstorms around Leonardtown and Rain Showers near Gwynn Oak.
Stop Ideas Near Upper Marlboro
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
United States Capitol
D C Government
THEARC: Town Hall Education Arts Recreation Campus
Kenhill Center
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Upper Marlboro.
New Carrollton station
Washington Union Station
Union Station
BWI Rail Station
Flight Path Map
This map shows the direct air route between Leonardtown and Gwynn Oak. Straight-line distance: 72.02 mi (115.9 km).
#1 Leonardtown
Town in Maryland, United States
| Population | 3,912 |
| Coordinates | 38.2912400, -76.6357900 |
| Altitude | 26 |
| Country | United States |
#2 Gwynn Oak
A census-designated place in Baltimore County, Maryland.
| Population | 47,092 |
| Coordinates | 39.3326100, -76.6927500 |
| Altitude | 130 |
| Country | United States |
End: (-76.692724, 39.332601)
Estimated Travel Time
Distance: 155 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 11m |
| 40 mph (64.37 km/h) | 02h 24m |
| 50 mph (80.47 km/h) | 01h 55m |
| 60 mph (96.56 km/h) | 01h 36m |
| 70 mph (112.65 km/h) | 01h 22m |
| 80 mph (129 km/h) | 01h 11m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.09 | $13.85 | $27.70 |
| Mid-grade | $4.60 | $15.59 | $31.18 |
| Premium | $4.95 | $16.79 | $33.59 |
| Diesel | $5.98 | $20.27 | $40.54 |
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 Maryland · Apr 19, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.