Origin
Annapolis, MD
Afternoon in Annapolis on Saturday
Local time
2:59 PM
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 Blue Star Memorial Highway, Church Hill Road, Centreville Road for much of the mileage, and the overall profile is mostly surface roads. The longest uninterrupted segment is about 26.7 miles on Blue Star Memorial Highway. At current regular gas prices, budget about $7.79 one way before food or hotel costs.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Blue Star Memorial Highway | 26.7 mi | 37m |
| Church Hill Road | 14.9 mi | 22m |
| Centreville Road | 2 mi | 3m |
| Roscoe Rowe Boulevard | 1.1 mi | 2m |
| South Commerce Street | 0.6 mi | 1m |
| Bladen Street | 0.3 mi | <1m |
| Maple Avenue | 0.2 mi | <1m |
| Chestertown Church Hill Road | 0.1 mi | <1m |
Longest stretch:
Blue Star Memorial Highway
— 26.7 mi, about 37m
Turn-by-Turn Driving Directions
Step-by-step road directions between Annapolis, MD and Chestertown, MD.
1
Start on School Street
137 ft
·
6 sec
·
School Street
2
Enter roundabout onto MD 450
77 ft
·
1 sec
·
College Avenue
3
Continue on MD 450
343 ft
·
7 sec
·
College Avenue
4
Turn left onto MD 70
0.3 mi
·
40 sec
·
Bladen Street
5
Continue on MD 70
1.1 mi
·
2 min
·
Roscoe Rowe Boulevard
6
Take the ramp
0.4 mi
·
45 sec
Toward US 50 East: Bay Bridge
7
Merge onto US 50; US 301; MD 2
21 mi
·
29 min
·
Blue Star Memorial Highway
Use the straight / slight right lanes.
8
Keep slight left at fork onto US 301
5.7 mi
·
8 min
·
Blue Star Memorial Highway
Toward US 301 North
9
Take the exit
0.3 mi
·
49 sec
Toward MD 213 North
10
Turn straight onto MD 213
2.0 mi
·
3 min
·
Centreville Road
11
Continue on MD 213
0.6 mi
·
1 min
·
South Commerce Street
12
Continue on MD 213
15 mi
·
22 min
·
Church Hill Road
13
Continue on MD 213
0.1 mi
·
13 sec
·
Chestertown Church Hill Road
14
Continue on MD 213
0.2 mi
·
27 sec
·
Maple Avenue
15
Turn left onto MD 289
0.1 mi
·
22 sec
·
North Cross Street
16
Arrive at destination
MD 289
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
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.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Heads-up: tricky spots
5 of 75 decision points cluster between mile 0 and 46.9 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
6
0 mi into trip
|
~0m in
|
MD 450 / College Avenue
Enter roundabout onto MD 450 / College Avenue
Roundabout - know your exit number before entering
5
1.9 mi into trip
|
~3m in
|
US 50; US 301; MD 2 / Blue Star Memorial Highway
Merge onto US 50; US 301; MD 2 / Blue Star Memorial Highway
Merge point - match speed before joining. Lane positioning matters here
Use the straight / slight right lanes.
5
22.8 mi into trip
|
~33m in
|
US 301 / Blue Star Memorial Highway
Keep slight left at fork onto US 301 / Blue Star Memorial Highway toward US 301 North
Highway fork - watch signs carefully
Toward US 301 North
4
28.6 mi into trip
|
~41m in
Take the exit toward MD 213 North
Exit ramp - move to the correct lane early
Toward MD 213 North
5
46.9 mi into trip
|
~1h 9m in
|
MD 289 / North Cross Street
Turn left onto MD 289 / North Cross Street
Navigation decision point
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 |
No toll roads detected on this route.
Drive Cost (one way)
Fuel
$8
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
Afternoon in Chestertown on Saturday
Local time
2:59 PM
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.
What kind of drive is this?
47 mi in 1h 9m across surface roads — expect steady turns and local traffic rather than long highway runs.
Only 0% highway — the rest is turn-by-turn surface driving.
16 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 26.7 mi on Blue Star Memorial Highway.
How Hard Is This Drive?
3/10
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. There are only a few real navigation decisions along the way. The trickiest moment comes early in the drive near MD 450 / College Avenue.
Driving Effort
3/10
Easy - simple navigation with a manageable amount of wheel time
Balances navigation complexity with total wheel time.
This is a straightforward 1h 9m drive. You will face about 7 decision points, but nothing that requires special attention if you follow navigation.
Where does it get tricky?
The main spots that need attention: near the start (MD 450 / College Avenue): Roundabout - know your exit number before entering; at 1.9 miles (US 50; US 301; MD 2 / Blue Star Memorial Highway): Merge point - match speed before joining. Lane positioning matters here; at 22.8 miles (US 301 / Blue Star Memorial Highway): Highway fork - watch signs carefully.
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
Mostly surface roads route profile.
Frequently Asked Questions
The longest stretch is about 26.7 miles on Blue Star Memorial Highway. The full list of main roads is in the Roads section above.
Yes. At under 2 hours behind the wheel, this works well for families — plan one quick stop if you have younger kids.
The main spots that need attention: near the start (MD 450 / College Avenue): Roundabout - know your exit number before entering; at 1.9 miles (US 50; US 301; MD 2 / Blue Star Memorial Highway): Merge point - match speed before joining. Lane positioning matters here; at 22.8 miles (US 301 / Blue Star Memorial Highway): Highway fork - watch signs carefully.
Yes. A round trip is manageable in a single day if you plan a break at Chestertown, MD before heading back.
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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