How far is Chestertown, MD from Annapolis, MD?
The driving distance from Chestertown, MD to Annapolis, MD is about 47.2 miles (75.9 km), with a travel time of about 00h 56m by car.
- The straight-line flight distance is about 27.8 miles (44.8 km).
- For a round trip, plan for roughly 01h 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 00h 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.
Census designated place
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Chestertown and Annapolis.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chestertown and Annapolis.
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1
Start on South Cross Street
770 ft · 27 sec · South Cross Street
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2
Turn right onto Maple Avenue
1196 ft · 20 sec · Maple Avenue
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3
Continue on Chestertown Church Hill Road
773 ft · 13 sec · Chestertown Church Hill Road
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4
Continue on Church Hill Road
14.9 mi · 22 min · Church Hill Road
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5
Continue on North Liberty Street
1.3 km · 2 min · North Liberty Street
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6
Continue on Centreville Road
1.8 mi · 3 min · Centreville Road
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7
Take the ramp right toward US 301 South
1367 ft · 38 sec
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8
Merge slight left onto Blue Star Memorial Highway
26.8 mi · 38 min · Blue Star Memorial Highway
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9
Take the exit slight right toward MD 70 South: Roscoe Rowe Boulevard, Annapolis
1470 ft · 36 sec
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10
Continue on Roscoe Rowe Boulevard
1.4 mi · 2 min · Roscoe Rowe Boulevard
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11
Keep slight right to continue on Roscoe Rowe Boulevard
667 ft · 13 sec · Roscoe Rowe Boulevard
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12
Turn left onto Northwest Street
792 ft · 23 sec · Northwest Street
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13
Enter the roundabout and take exit 5 toward Church Circle
544 ft · 17 sec · School Street
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14
Exit the rotary onto School Street
42 m · 6 sec · School Street
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15
Arrive at your destination
0 m · 1 sec · School Street
Car Route Details
A richer read on the saved driving route between Chestertown and Annapolis.
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
26.8 mi · 00h 38m
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.
Mostly Sunny leaving Chestertown and Mostly Sunny near Annapolis.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chestertown to Annapolis?
The road trip is about 47.2 miles (75.9 km) and usually takes 00h 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?
Grasonville is a useful midpoint, sitting about 23.5 miles from Chestertown and 23.6 miles from Annapolis.
How much longer is the road route than the straight-line distance?
The direct path is about 27.8 miles (44.8 km), while the road route adds roughly 19.4 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 4:36 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $6.78 one way or $13.57 round trip. Estimated CO2 is about 14.8 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Chestertown and Mostly Sunny near Annapolis.
Stop Ideas Near Grasonville
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 Grasonville.
Kent Island, MD
Easton Airport, Maryland
Cambridge, Maryland
BWI Rail Station
Flight Path Map
This map shows the direct air route between Chestertown and Annapolis. Straight-line distance: 27.81 mi (44.76 km).
#1 Chestertown
Town in Maryland, United States
| Population | 5,001 |
| Coordinates | 39.2090000, -76.0666100 |
| Altitude | 4 |
| Country | United States |
#2 Annapolis
City in and county seat of Anne Arundel County, Maryland, United States, and Maryland federated state capital city
| Population | 39,524 |
| Coordinates | 38.9785900, -76.4918400 |
| Altitude | 12 |
| Country | United States |
End: School Street (-76.491792, 38.978586)
Estimated Travel Time
Distance: 76 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 34m |
| 40 mph (64.37 km/h) | 01h 10m |
| 50 mph (80.47 km/h) | 00h 56m |
| 60 mph (96.56 km/h) | 00h 47m |
| 70 mph (112.65 km/h) | 00h 40m |
| 80 mph (129 km/h) | 00h 35m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.09 | $6.78 | $13.57 |
| Mid-grade | $4.60 | $7.63 | $15.27 |
| Premium | $4.95 | $8.22 | $16.45 |
| Diesel | $5.98 | $9.93 | $19.85 |
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 18, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.