How far is Rockville, MD from Chestertown, MD?
The driving distance from Rockville, MD to Chestertown, MD is about 88.5 miles (142.4 km), with a travel time of about 02h 02m by car.
- The straight-line flight distance is about 58.8 miles (94.7 km).
- For a round trip, plan for roughly 04h 05m 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 02h 02m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
This departure sits inside the recommended comfort window for the route.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
City in and county seat of Anne Arundel County, Maryland, United States, and Maryland federated state capital city
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 Rockville and Chestertown.
Turn-by-Turn Driving Directions
Step-by-step road directions between Rockville and Chestertown.
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1
Start on South Washington Street
19 m · 9 sec · South Washington Street
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2
Turn left onto West Montgomery Avenue
1144 ft · 34 sec · West Montgomery Avenue
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3
Continue on Great Falls Road
1 km · 2 min · Great Falls Road
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4
Turn right onto Falls Road
132 m · 17 sec · Falls Road
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5
Continue on Falls Road
144 m · 18 sec · Falls Road
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6
Take the ramp slight left toward I 270 South
1769 ft · 51 sec
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7
Merge slight left
2.6 mi · 3 min
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8
Keep slight left to continue on I 270 South: Silver Spring, College Park
2.8 mi · 4 min
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9
Merge slight right onto Capital Beltway
16.3 mi · 21 min · Capital Beltway
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10
Take the exit slight right toward US 50 East: Annapolis
1 mi · 2 min
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11
Merge slight left onto John Hanson Highway
18.7 mi · 22 min · John Hanson Highway
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12
Continue on Blue Star Memorial Highway
21.6 mi · 30 min · Blue Star Memorial Highway
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13
Keep slight left to continue on Blue Star Memorial Highway
5.7 mi · 8 min · Blue Star Memorial Highway
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14
Take the exit slight right toward MD 213 North
1814 ft · 50 sec
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15
Turn straight onto Centreville Road
2 mi · 3 min · Centreville Road
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16
Continue on South Commerce Street
1 km · 1 min · South Commerce Street
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17
Continue on Church Hill Road
14.9 mi · 22 min · Church Hill Road
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18
Continue on Chestertown Church Hill Road
773 ft · 13 sec · Chestertown Church Hill Road
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19
Continue on Maple Avenue
1196 ft · 28 sec · Maple Avenue
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20
Turn left onto North Cross Street
770 ft · 23 sec · North Cross Street
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21
Arrive at your destination
0 m · 1 sec · South Cross Street
Car Route Details
A richer read on the saved driving route between Rockville 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
Continue on Blue Star Memorial Highway
21.6 mi · 00h 30m
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 Rockville and Sunny near Chestertown.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Rockville to Chestertown?
The road trip is about 88.5 miles (142.4 km) and usually takes 02h 02m 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?
Annapolis is a useful midpoint, sitting about 44.2 miles from Rockville and 44.3 miles from Chestertown.
How much longer is the road route than the straight-line distance?
The direct path is about 58.8 miles (94.7 km), while the road route adds roughly 29.7 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 2:24 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $12.75 one way or $25.50 round trip. Estimated CO2 is about 27.7 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Rockville and Sunny near Chestertown.
Stop Ideas Near Annapolis
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
City of Bowie
Annapolis City Hall
Kenhill Center
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Annapolis.
Kent Island, MD
BWI Rail Station
New Carrollton station
Pennsylvania Station
Flight Path Map
This map shows the direct air route between Rockville and Chestertown. Straight-line distance: 58.84 mi (94.69 km).
#1 Rockville
The most populous city in Montgomery County, Maryland.
| Population | 69,512 |
| Coordinates | 39.0840000, -77.1527600 |
| Altitude | 137 |
| 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: 142 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 56m |
| 40 mph (64.37 km/h) | 02h 12m |
| 50 mph (80.47 km/h) | 01h 46m |
| 60 mph (96.56 km/h) | 01h 28m |
| 70 mph (112.65 km/h) | 01h 15m |
| 80 mph (129 km/h) | 01h 06m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.09 | $12.75 | $25.50 |
| Mid-grade | $4.60 | $14.35 | $28.70 |
| Premium | $4.95 | $15.46 | $30.91 |
| Diesel | $5.98 | $18.66 | $37.32 |
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 · May 05, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.