Origin
Chestertown, MD
Morning in Chestertown on Saturday
Local time
10:54 AM
EDT
Current temp
75°F
Unavailable
Live forecast
Trip from Chestertown, MD to Annapolis, MD
Compiled and reviewed by the Trip.ovh planning team at COD Solutions Oy · Last reviewed Apr 18, 2026 · Editorial standards
Drive Time
56m
Distance
47.2 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
0h 52m
★
6 AM
0h 57m
8 AM
1h 6m
10 AM
1h 0m
12 PM
0h 59m
3 PM
1h 1m
5 PM
1h 6m
8 PM
0h 54m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Chestertown, MD
Wikimedia Commons
Annapolis, MD
Wikimedia Commons
Trip Overview
The drive from Chestertown, MD to Annapolis, MD covers 47.2 miles and takes about 56m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Maple Avenue, Chestertown Church Hill Road, Church Hill Road for much of the mileage, and the overall profile is turn-heavy local drive. At current regular gas prices, budget about $7.83 one way before food or hotel costs.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 56m. Total distance: 47.2 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
56m 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 56m drive with frequent turns across 47.2 miles of local and secondary roads.
This route has more turning and local-road decision points than a simple highway run.
There are about 15 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Maple Avenue 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 Chestertown, MD to Annapolis, MD is easy. At 56m 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 Chestertown, MD to Annapolis, MD is straightforward, with well-signed roads and simple exits.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Maple Avenue | — | — |
| Chestertown Church Hill Road | — | — |
| Church Hill Road | — | — |
| North Liberty Street | — | — |
| Centreville Road | — | — |
| US 301 South | — | — |
| Blue Star Memorial Highway | — | — |
| MD 70 South | — | — |
Some road-level metrics are being recalculated.
Longest stretch:
Maple Avenue
— detailed segment metrics are refreshing.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chestertown, MD and Annapolis, MD.
1
Start on South Cross Street
0.1 mi
·
27 sec
·
South Cross Street
2
Turn right onto Maple Avenue
0.2 mi
·
20 sec
·
Maple Avenue
3
Continue on Chestertown Church Hill Road
0.1 mi
·
13 sec
·
Chestertown Church Hill Road
4
Continue on Church Hill Road
15 mi
·
22 min
·
Church Hill Road
5
Continue on North Liberty Street
0.8 mi
·
1 min
·
North Liberty Street
6
Continue on Centreville Road
1.8 mi
·
2 min
·
Centreville Road
7
Take the ramp right toward US 301 South
0.3 mi
·
38 sec
·
US 301 South
8
Merge slight left onto Blue Star Memorial Highway
27 mi
·
37 min
·
Blue Star Memorial Highway
9
Take the exit slight right toward MD 70 South: Roscoe Rowe Boulevard, Annapolis
0.3 mi
·
36 sec
·
MD 70 South: Roscoe Rowe Boulevard, Annapolis
10
Continue on Roscoe Rowe Boulevard
1.4 mi
·
2 min
·
Roscoe Rowe Boulevard
11
Keep slight right to continue on Roscoe Rowe Boulevard
0.1 mi
·
13 sec
·
Roscoe Rowe Boulevard
12
Turn left onto Northwest Street
0.1 mi
·
23 sec
·
Northwest Street
13
Enter the roundabout and take exit 5 toward Church Circle
0.1 mi
·
17 sec
·
Church Circle
14
Exit the rotary onto School Street
138 ft
·
6 sec
·
School Street
15
Arrive at your destination
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 23.6 mi from Chestertown, MD · 28m 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 23.6 miles from Chestertown, MD, which is a good place for a longer meal and fuel stop.
Arriving in Annapolis, MD
Allow a few extra minutes for the final approach into Annapolis, MD if you are unfamiliar with the area.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Fuel & Cost
Regular Gas
$7.83 one way
$15.65 round trip
$4.21/gal
25.4 MPG avg
17 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.61 | $8.57 | $17.14 |
| premium | $4.93 | $9.15 | $18.31 |
| diesel | $5.61 | $10.42 | $20.84 |
No toll roads detected on this route.
Drive Cost (one way)
Fuel
$8
Estimated CO2 emission: 16.5 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $5 in charging · 0 stops · 65% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 14.2 | 0 | $4.96 | $2.27 |
| Efficient EV | 11.8 | 0 | $4.13 | $1.89 |
| EV Truck/SUV | 18.9 | 0 | $6.61 | $3.02 |
Gas CO2
17 kg
EV CO2
6 kg (65% 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
Annapolis, MD
Morning in Annapolis on Saturday
Local time
10:54 AM
EDT
Current temp
74°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 cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
56m 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 Chestertown, MD to Annapolis, MD covers 47.2 miles and takes about 56m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Maple Avenue, Chestertown Church Hill Road, Church Hill Road. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 23.6 miles from Chestertown, MD. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $7.83 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 Chestertown, MD to Annapolis, MD is easy. At 56m 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 Chestertown, MD to Annapolis, MD is straightforward, with well-signed roads and simple exits.
The route from Chestertown, MD to Annapolis, 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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