Origin
Annapolis, MD
Morning in Annapolis on Saturday
Local time
10:54 AM
EDT
Current temp
74°F
Unavailable
Live forecast
Trip from Annapolis, MD to Chestertown, MD
Compiled and reviewed by the Trip.ovh planning team at COD Solutions Oy · Last reviewed Apr 18, 2026 · Editorial standards
Drive Time
1h 9m
Distance
47 mi
76 km
Drive Score
6/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$8
one way
EV Charging
Unknown
Best Time to Leave
4 AM
1h 4m
★
6 AM
1h 9m
8 AM
1h 21m
10 AM
1h 13m
12 PM
1h 12m
3 PM
1h 14m
5 PM
1h 20m
8 PM
1h 6m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Annapolis, MD
Wikimedia Commons
Chestertown, MD
Wikimedia Commons
Trip Overview
The drive from Annapolis, MD to Chestertown, MD covers 47 miles and takes about 1h 9m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Church Circle, College Avenue, Bladen Street for much of the mileage, and the overall profile is turn-heavy local drive. At current regular gas prices, budget about $7.79 one way before food or hotel costs.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 1h 9m. Total distance: 47 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 9m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (0%). Straightforward navigation.
Scenic Drive
Turn-heavy local drive route profile.
Drive Character
Expect a 1h 9m drive with frequent turns across 47 miles of local and secondary roads.
This route has more turning and local-road decision points than a simple highway run.
There are about 16 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Church Circle is one of the defining roads on this drive.
How Hard Is This Drive?
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. Navigation is very simple - set it and forget it for most of the drive.
Driving Effort
1/10
Very easy - short and simple to drive
Balances navigation complexity with total wheel time.
The drive from Annapolis, MD to Chestertown, MD is easy. At 1h 9m with 0% highway, most drivers will find it relaxed and low-stress.
Where does it get tricky?
This route does not have any notably tricky sections. Most of the drive from Annapolis, MD to Chestertown, MD is straightforward, with well-signed roads and simple exits.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Church Circle | — | — |
| College Avenue | — | — |
| Bladen Street | — | — |
| Roscoe Rowe Boulevard | — | — |
| US 50 East | — | — |
| Blue Star Memorial Highway | — | — |
| MD 213 North | — | — |
| Centreville Road | — | — |
Some road-level metrics are being recalculated.
Longest stretch:
Church Circle
— detailed segment metrics are refreshing.
Turn-by-Turn Driving Directions
Step-by-step road directions between Annapolis, MD and Chestertown, MD.
1
Start on School Street
138 ft
·
6 sec
·
School Street
2
Enter the roundabout and take exit 1 toward Church Circle
79 ft
·
2 sec
·
Church Circle
3
Exit the rotary onto College Avenue
344 ft
·
7 sec
·
College Avenue
4
Turn left onto Bladen Street
0.3 mi
·
41 sec
·
Bladen Street
5
Continue on Roscoe Rowe Boulevard
1.1 mi
·
2 min
·
Roscoe Rowe Boulevard
6
Take the ramp slight right toward US 50 East: Bay Bridge
0.4 mi
·
46 sec
·
US 50 East: Bay Bridge
7
Merge slight left onto Blue Star Memorial Highway
21 mi
·
29 min
·
Blue Star Memorial Highway
8
Keep slight left to continue on Blue Star Memorial Highway
5.7 mi
·
8 min
·
Blue Star Memorial Highway
9
Take the exit slight right toward MD 213 North
0.3 mi
·
50 sec
·
MD 213 North
10
Turn straight onto Centreville Road
2.0 mi
·
3 min
·
Centreville Road
11
Continue on South Commerce Street
0.6 mi
·
1 min
·
South Commerce Street
12
Continue on Church Hill Road
15 mi
·
22 min
·
Church Hill Road
13
Continue on Chestertown Church Hill Road
0.1 mi
·
13 sec
·
Chestertown Church Hill Road
14
Continue on Maple Avenue
0.2 mi
·
28 sec
·
Maple Avenue
15
Turn left onto North Cross Street
0.1 mi
·
23 sec
·
North Cross Street
16
Arrive at your destination
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 23.5 mi from Annapolis, MD · 34m into the drive
Mid-route town
Meal stop
24 mi into the route
Best for: Lunch, fuel, and a longer reset
This sits close to the middle of the route, so it works well for the longest stop of the day.
Pacing Suggestions
Fuel and coffee
A short stop after about 10 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 23.5 miles from Annapolis, MD, which is a good place for a longer meal and fuel stop.
Arriving in Chestertown, MD
The final approach into Chestertown, MD usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Fuel & Cost
Regular Gas
$7.79 one way
$15.58 round trip
$4.21/gal
25.4 MPG avg
16 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.61 | $8.53 | $17.07 |
| premium | $4.93 | $9.12 | $18.23 |
| diesel | $5.61 | $10.38 | $20.75 |
Estimated Tolls: $7.00
Bay Bridge
$7.00
Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.
Drive Cost (one way)
Fuel
$8
Tolls
$7
Total
$15
Estimated CO2 emission: 16.4 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $5 in charging · 0 stops · 69% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 14.1 | 0 | $4.94 | $2.26 |
| Efficient EV | 11.8 | 0 | $4.11 | $1.88 |
| EV Truck/SUV | 18.8 | 0 | $6.58 | $3.01 |
Gas CO2
16 kg
EV CO2
5 kg (69% less)
This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.
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.
Destination
Chestertown, MD
Morning in Chestertown on Saturday
Local time
10:54 AM
EDT
Current temp
75°F
Unavailable
Live forecast
Time zone
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
1 degrees warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
1h 9m on the road
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
Frequently Asked Questions
The drive from Annapolis, MD to Chestertown, MD covers 47 miles and takes about 1h 9m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Church Circle, College Avenue, Bladen Street. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 23.5 miles from Annapolis, MD. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $7.79 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.
The drive from Annapolis, MD to Chestertown, MD is easy. At 1h 9m with 0% highway, most drivers will find it relaxed and low-stress.
This route does not have any notably tricky sections. Most of the drive from Annapolis, MD to Chestertown, MD is straightforward, with well-signed roads and simple exits.
The route from Annapolis, MD to Chestertown, MD does not surface many named destination signs beyond the main corridor.
How this page is built
Compiled by the Trip.ovh planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, and EIA for fuel prices. See our methodology for refresh cadence and limitations.
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