Frederick, MD to Chestertown, MD is 107.9 miles and takes about 2h 24m via I 70 and Blue Star Memorial Highway, with a fuel budget near $18 and enough daylight to finish in a day. This drive stays within Maryland, moving from the Northeast region towards the Eastern Shore. Expect a mixed driving experience with a significant portion on interstates before transitioning to surface roads. This is a manageable one-day trip, perfect if you're looking for a straightforward drive to a new destination.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
53.9 miles from Frederick, MD
A natural place for your longest stop of the day
, about 1h 5m into the drive
.
Main Roads
Road
Distance
Duration
I 70
32.1 mi
34m
Blue Star Memorial Highway
24.8 mi
35m
MD 100
17.5 mi
23m
Church Hill Road
14.9 mi
22m
Governor Ritchie Highway
6.1 mi
8m
Ritchie Highway
2.4 mi
3m
Columbia Pike
2.3 mi
2m
Centreville Road
2 mi
3m
Longest stretch:
I 70
— 32.1 mi, about 34m
Turn-by-Turn Driving Directions
Step-by-step road directions between Frederick, MD and Chestertown, MD.
1
Start on MD 144
122 ft·7 sec·East Patrick Street
2
Turn right onto North Market Street
435 ft·18 sec·North Market Street
3
Turn right onto East Church Street
0.3 mi·47 sec·East Church Street
4
Turn right onto North East Street
0.6 mi·1 min·North East Street
Use the straight / right lanes.
5
Enter roundabout onto East Street
101 ft·1 sec·East Street
6
Continue on East Street
0.1 mi·14 sec·East Street
7
Continue on MD 85
0.2 mi·17 sec·Buckeystown Pike
8
Take the ramp
0.4 mi·45 sec
Toward I 70 East, US 40 East
9
Merge onto I 70; US 40
21 mi·22 min·I 70; US 40
Use the straight / slight right lanes.
10
Continue on I 70; US 40
6.5 mi·6 min·I 70; US 40
Use the straight / slight right lanes.
11
Keep slight left at fork onto I 70
4.6 mi·4 min·I 70
Toward Baltimore
12
Take the exit
0.7 mi·1 min
Exit 87AToward US 29 South: Columbia, WashingtonUse the straight / slight right lanes.
13
Merge onto US 29
2.3 mi·2 min·Columbia Pike
Use the straight / slight right lanes.
14
Take the exit
0.5 mi·43 sec
Exit 22Toward MD 100 East: Glen BurnieUse the slight left / straight lanes.
15
Continue on MD 100
18 mi·23 min·MD 100
Use the straight / slight right lanes.
16
Merge onto MD 10; MD 100
0.3 mi·25 sec·Arundel Expressway
17
Keep slight right at fork onto MD 10
0.7 mi·1 min·Arundel Expressway
Toward MD 10 South: Severna ParkUse the slight right lane.
18
Turn left onto MD 2
2.4 mi·3 min·Ritchie Highway
19
Continue on MD 2
6.1 mi·8 min·Governor Ritchie Highway
Use the straight lane.
20
Take the exit
0.2 mi·22 sec
Toward US 50 East, US 301 North: Bay Bridge
21
Merge onto US 50; US 301
19 mi·27 min·Blue Star Memorial Highway
Use the straight / slight right lanes.
22
Keep slight left at fork onto US 301
5.7 mi·8 min·Blue Star Memorial Highway
Toward US 301 North
23
Take the exit
0.3 mi·49 sec
Toward MD 213 North
24
Turn straight onto MD 213
2.0 mi·3 min·Centreville Road
25
Continue on MD 213
0.6 mi·1 min·South Commerce Street
26
Continue on MD 213
15 mi·22 min·Church Hill Road
27
Continue on MD 213
0.1 mi·13 sec·Chestertown Church Hill Road
28
Continue on MD 213
0.2 mi·27 sec·Maple Avenue
29
Turn left onto MD 289
0.1 mi·22 sec·North Cross Street
30
Arrive at destination
MD 289
Trip Plan
With a total duration of around 2 hours and 24 minutes, this trip is easily completed in a single day. Consider leaving mid-morning to avoid the worst of any rush hour traffic around Frederick. Since the drive is relatively short, you have flexibility with stops; however, plan for a fuel stop before you leave Frederick, as the estimated fuel cost is $18. Keep an eye on your GPS as you transition from I 70 onto the Blue Star Memorial Highway and MD 100, as the road type and speed limits will change.
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 53.9 miles from Frederick, MD, or about 1h 5m into the drive.
The longest continuous stretch on this route runs about 32.1 miles.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 24 miles or 28m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 53.9 miles or 1h 5m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 55m
Traffic, exits, and arrival timing usually matter more near Chestertown, MD than in the middle of the route.
Before You Leave
+
Open the route before leaving Frederick, MD so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Frederick, MD
This is one driving day of about 107.9 miles and 2h 24m.
Your first comfortable stop window is around 24 miles from Frederick, MD.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on I 70 for about 32.1 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 17
5 decision points cluster between mile 0 and 55.3 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
0 mi into trip|~0m in|North Market Street
Turn right onto North Market Street
Navigation decision point
6
0.4 mi into trip|~1m in|North East Street
Turn right onto North East Street
Lane positioning matters here
Use the straight / right lanes.
8
33.8 mi into trip|~38m in
Take the exit toward US 29 South: Columbia, Washington
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 87A
Toward US 29 South: Columbia, Washington
7
36.9 mi into trip|~42m in
Take the exit toward MD 100 East: Glen Burnie
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight left / straight lanes.
Exit 22
Toward MD 100 East: Glen Burnie
7
55.3 mi into trip|~1h 7m in|MD 10 / Arundel Expressway
Keep slight right at fork onto MD 10 / Arundel Expressway toward MD 10 South: Severna Park
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Toward MD 10 South: Severna Park
Fuel & Cost
Regular Gas
$17.89 one way
$35.78 round trip
$4.21/gal25.4 MPG avg38 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.61
$19.59
$39.18
premium
$4.93
$20.93
$41.85
diesel
$5.61
$23.82
$47.65
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$18
Meals
$25–$50
Total
$43–$68
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 37.8 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $11 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
32.4
0
$11.33
$5.18
Efficient EV
27
0
$9.44
$4.32
EV Truck/SUV
43.2
0
$15.11
$6.91
Gas CO2
38 kg
EV CO2
13 kg (66% 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.
Forecast as of Apr 20, 2026
Origin
Frederick, MD
Late night
in Frederick on Tuesday
Local time
5:36 AM
EDT
Current temp
63°F
Unavailable
Live forecast
Destination
Chestertown, MD
Late night
in Chestertown on Tuesday
Local time
5:36 AM
EDT
Current temp
49°F
Unavailable
Live forecast
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
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
14 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
2h 24m 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.
More Details
What kind of drive is this?
About 47% of this 107.9-mile route is on highways. You'll spend the longest stretch, 32.1 miles, on I 70. The highway portion will likely transition to surface roads around the MD 100 area. Be prepared for merging traffic and a change in speed limits as you move from the interstate environment to more local roadways.
47% highway, the rest on surface roads — varied driving throughout.
30 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 32.1 mi on I 70.
How Hard Is This Drive?
10/10
This route mixes highway mileage with some local-road sections near the start or finish. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes early in the drive near North Market Street.
Driving Effort10/10
High effort - long or complex enough to need steady focus all day
Balances navigation complexity with total wheel time.
This is a demanding drive. With 17 significant decision points across 107.9 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: near the start (North Market Street): Navigation decision point; at 0.4 miles (North East Street): Lane positioning matters here; at 33.8 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Frederick, MD and Chestertown, MD, road signs point toward Baltimore and Washington.
Frederick is a charming city of approximately 80,000 people (2020) in Maryland. It is a major antique center with many shops, eateries, galleries and antique dealers.
Doable as a same-day drive at 2h 24m. Total distance: 107.9 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
2h 24m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (47%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 32.1 miles on I 70. The full list of main roads is in the Roads section above.
Yes — we found about 3 rest areas or service plazas within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Chestertown, MD before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. There are 3 rest areas along the route for bathroom stops.
The main spots that need attention: near the start (North Market Street): Navigation decision point; at 0.4 miles (North East Street): Lane positioning matters here; at 33.8 miles: Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes. A round trip is manageable in a single day if you plan a break at Chestertown, MD before heading back.
