How far is Gwynn Oak, MD from Chestertown, MD?
The driving distance from Gwynn Oak, MD to Chestertown, MD is about 73.5 miles (118.3 km), with a travel time of about 01h 50m by car.
- The straight-line flight distance is about 34.5 miles (55.6 km).
- For a round trip, plan for roughly 03h 41m 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 50m.
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 Montana, USA
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 Gwynn Oak and Chestertown.
Turn-by-Turn Driving Directions
Step-by-step road directions between Gwynn Oak and Chestertown.
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1
Start on the route
18 m · 6 sec
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2
Turn right onto Haddon Avenue
54 m · 12 sec · Haddon Avenue
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3
Turn left onto Hillsdale Road
1.5 km · 3 min · Hillsdale Road
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4
Turn slight right onto West Forest Park Avenue
1.4 mi · 4 min · West Forest Park Avenue
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5
Continue on Ingleside Avenue
1.6 mi · 3 min · Ingleside Avenue
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6
Turn right onto Baltimore National Pike
2671 ft · 56 sec · Baltimore National Pike
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7
Take the ramp left toward I 695 South: Glen Burnie
2015 ft · 51 sec
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8
Merge slight left onto Baltimore Beltway
9.5 mi · 13 min · Baltimore Beltway
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9
Take the exit slight right toward MD 10 South: Severna Park
3143 ft · 1 min
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10
Continue on Arundel Expressway
5.9 mi · 8 min · Arundel Expressway
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11
Keep slight right to continue on Arundel Expressway
1.2 km · 1 min · Arundel Expressway
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12
Turn left onto Ritchie Highway
2.4 mi · 3 min · Ritchie Highway
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13
Continue on Governor Ritchie Highway
6.1 mi · 9 min · Governor Ritchie Highway
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14
Take the exit slight left toward US 50 East, US 301 North: Bay Bridge
919 ft · 23 sec
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15
Merge slight left onto Blue Star Memorial Highway
19.1 mi · 27 min · Blue Star Memorial Highway
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16
Keep slight left to continue on Blue Star Memorial Highway
5.7 mi · 8 min · Blue Star Memorial Highway
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17
Take the exit slight right toward MD 213 North
1814 ft · 50 sec
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18
Turn straight onto Centreville Road
2 mi · 3 min · Centreville Road
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19
Continue on South Commerce Street
1 km · 1 min · South Commerce Street
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20
Continue on Church Hill Road
14.9 mi · 22 min · Church Hill Road
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21
Continue on Chestertown Church Hill Road
773 ft · 13 sec · Chestertown Church Hill Road
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22
Continue on Maple Avenue
1196 ft · 28 sec · Maple Avenue
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23
Turn left onto North Cross Street
770 ft · 23 sec · North Cross Street
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24
Arrive at your destination
0 m · 1 sec · South Cross Street
Car Route Details
A richer read on the saved driving route between Gwynn Oak and Chestertown.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Blue Star Memorial Highway
Merge slight left onto Blue Star Memorial Highway
19.1 mi · 00h 27m
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.
Sunny leaving Gwynn Oak and Sunny near Chestertown.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Gwynn Oak to Chestertown?
The road trip is about 73.5 miles (118.3 km) and usually takes 01h 50m 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?
Stevensville is a useful midpoint, sitting about 36.7 miles from Gwynn Oak and 36.8 miles from Chestertown.
How much longer is the road route than the straight-line distance?
The direct path is about 34.5 miles (55.6 km), while the road route adds roughly 39 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 2:48 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $10.58 one way or $21.17 round trip. Estimated CO2 is about 23 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Gwynn Oak and Sunny near Chestertown.
Stop Ideas Near Stevensville
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Stevensville.
Kent Island, MD
Easton Airport, Maryland
BWI Rail Station
Pennsylvania Station
Flight Path Map
This map shows the direct air route between Gwynn Oak and Chestertown. Straight-line distance: 34.56 mi (55.62 km).
#1 Gwynn Oak
A census-designated place in Baltimore County, Maryland.
| Population | 47,092 |
| Coordinates | 39.3326100, -76.6927500 |
| Altitude | 130 |
| Country | United States |
#2 Chestertown
Town in Maryland, United States
| Population | 5,001 |
| Coordinates | 39.2090000, -76.0666100 |
| Altitude | 4 |
| Country | United States |
End: Chestertown (-76.06661, 39.209)
Estimated Travel Time
Distance: 118 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 26m |
| 40 mph (64.37 km/h) | 01h 50m |
| 50 mph (80.47 km/h) | 01h 28m |
| 60 mph (96.56 km/h) | 01h 13m |
| 70 mph (112.65 km/h) | 01h 02m |
| 80 mph (129 km/h) | 00h 55m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.09 | $10.58 | $21.17 |
| Mid-grade | $4.60 | $11.91 | $23.82 |
| Premium | $4.95 | $12.83 | $25.66 |
| Diesel | $5.98 | $15.49 | $30.98 |
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 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.