Origin
Chestertown, MD
Afternoon in Chestertown on Saturday
Local time
4:17 PM
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
1h 10m
Distance
47.1 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 10m
8 AM
1h 21m
10 AM
1h 14m
12 PM
1h 13m
3 PM
1h 15m
5 PM
1h 21m
8 PM
1h 7m
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 47.1 miles and takes about 1h 10m 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 26.8 miles on Blue Star Memorial Highway. At current regular gas prices, budget about $7.81 one way before food or hotel costs.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Blue Star Memorial Highway | 26.8 mi | 37m |
| Church Hill Road | 14.9 mi | 22m |
| Centreville Road | 1.8 mi | 2m |
| Roscoe Rowe Boulevard | 1.5 mi | 2m |
| North Liberty Street | 0.8 mi | 1m |
| Maple Avenue | 0.2 mi | <1m |
| Northwest Street | 0.1 mi | <1m |
| Chestertown Church Hill Road | 0.1 mi | <1m |
Longest stretch:
Blue Star Memorial Highway
— 26.8 mi, about 37m
Turn-by-Turn Driving Directions
Step-by-step road directions between Chestertown, MD and Annapolis, MD.
1
Start on MD 289
0.1 mi
·
26 sec
·
South Cross Street
2
Turn right onto MD 213
0.2 mi
·
20 sec
·
Maple Avenue
3
Continue on MD 213
0.1 mi
·
13 sec
·
Chestertown Church Hill Road
4
Continue on MD 213
15 mi
·
22 min
·
Church Hill Road
5
Continue on MD 213
0.8 mi
·
1 min
·
North Liberty Street
6
Continue on MD 213
1.8 mi
·
2 min
·
Centreville Road
7
Take the ramp
0.3 mi
·
37 sec
Toward US 301 South
8
Merge onto US 301
27 mi
·
37 min
·
Blue Star Memorial Highway
Use the straight / slight right lanes.
9
Take the exit
0.3 mi
·
35 sec
Exit 24A
Toward MD 70 South: Roscoe Rowe Boulevard, Annapolis
Use the right lane.
10
Continue on MD 70
1.4 mi
·
2 min
·
Roscoe Rowe Boulevard
Use the straight lane.
11
Keep slight right at fork onto Roscoe Rowe Boulevard
0.1 mi
·
13 sec
·
Roscoe Rowe Boulevard
12
Turn left onto Northwest Street
0.1 mi
·
22 sec
·
Northwest Street
13
Enter roundabout onto School Street
0.1 mi
·
16 sec
·
School Street
14
Continue on School Street
137 ft
·
5 sec
·
School Street
15
Arrive at destination
School Street
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 23.6 miles from Chestertown, 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 85 decision points cluster between mile 0.1 and 47 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
0.1 mi into trip
|
~0m in
|
MD 213 / Maple Avenue
Turn right onto MD 213 / Maple Avenue
Navigation decision point
5
18 mi into trip
|
~27m in
Take the ramp toward US 301 South
Navigation decision point
Toward US 301 South
5
18.3 mi into trip
|
~28m in
|
US 301 / Blue Star Memorial Highway
Merge onto US 301 / Blue Star Memorial Highway
Merge point - match speed before joining. Lane positioning matters here
Use the straight / slight right lanes.
8
45 mi into trip
|
~1h 6m in
Take the exit toward MD 70 South: Roscoe Rowe Boulevard, Annapolis
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the right lane.
Exit 24A
Toward MD 70 South: Roscoe Rowe Boulevard, Anna...
6
47 mi into trip
|
~1h 9m in
|
School Street
Enter roundabout onto School Street
Roundabout - know your exit number before entering
Fuel & Cost
Regular Gas
$7.81 one way
$15.62 round trip
$4.21/gal
25.4 MPG avg
17 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.61 | $8.55 | $17.10 |
| premium | $4.93 | $9.13 | $18.27 |
| diesel | $5.61 | $10.40 | $20.80 |
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 · 63% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 14.1 | 0 | $4.95 | $2.26 |
| Efficient EV | 11.8 | 0 | $4.12 | $1.88 |
| EV Truck/SUV | 18.8 | 0 | $6.59 | $3.01 |
Gas CO2
16 kg
EV CO2
6 kg (63% 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
Afternoon in Annapolis on Saturday
Local time
4:17 PM
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
1h 10m 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?
47.1 mi in 1h 10m 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.
15 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 26.8 mi on Blue Star Memorial Highway.
How Hard Is This Drive?
5/10
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. You will hit about 8 points where you need to pay attention to lane position or signs. The trickiest moment comes around 0.1 miles in near MD 213 / Maple Avenue.
Driving Effort
5/10
Moderate - straightforward overall, but long enough or busy enough to require pacing
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 47.1 miles you will encounter 8 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
Where does it get tricky?
The main spots that need attention: at 0.1 miles (MD 213 / Maple Avenue): Navigation decision point; at 18 miles: Navigation decision point; at 18.3 miles (US 301 / Blue Star Memorial Highway): Merge point - match speed before joining. Lane positioning matters here.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 1h 10m. Total distance: 47.1 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 10m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (0%). Some complex stretches to watch for.
Scenic Drive
Mostly surface roads route profile.
Frequently Asked Questions
The longest stretch is about 26.8 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: at 0.1 miles (MD 213 / Maple Avenue): Navigation decision point; at 18 miles: Navigation decision point; at 18.3 miles (US 301 / Blue Star Memorial Highway): Merge point - match speed before joining. Lane positioning matters here.
Yes. A round trip is manageable in a single day if you plan a break at Annapolis, 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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