Essex, MD to Chestertown, MD is 72.5 miles and takes about 1h 50m via Blue Star Memorial Highway, with a fuel budget near $12 and enough daylight to finish in a day. This trip stays within Maryland, connecting two points in the Northeast region. Expect a mostly surface road experience, making it a straightforward drive. It's a good option for a single-day excursion, offering a manageable distance for a relaxed pace.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
36.3 miles from Essex, MD
A natural place for your longest stop of the day
, about 57m into the drive
.
Main Roads
Road
Distance
Duration
Blue Star Memorial Highway
24.8 mi
35m
Church Hill Road
14.9 mi
22m
Governor Ritchie Highway
6.1 mi
8m
Arundel Expressway
4.7 mi
6m
Harbor Tunnel Thruway
4 mi
5m
Ritchie Highway
3.5 mi
5m
Harbor Tunnel Throughway
3.4 mi
4m
Centreville Road
2 mi
3m
Longest stretch:
Blue Star Memorial Highway
— 24.8 mi, about 35m
Turn-by-Turn Driving Directions
Step-by-step road directions between Essex, MD and Chestertown, MD.
1
Start on this road
359 ft·31 sec·this road
2
Turn left
184 ft·15 sec
3
At end of road, turn right onto MD 150
1.0 mi·2 min·Eastern Boulevard
4
Continue on MD 150
1.3 mi·2 min·Eastern Avenue
Use the right lane.
5
Turn slight right
0.3 mi·48 sec
Toward MD 151 North: North Point Boulevard, BaltimoreUse the right lane.
6
Turn straight onto MD 151
0.5 mi·53 sec·North Point Boulevard
7
Turn left onto Kane Street
0.2 mi·34 sec·Kane Street
8
Turn slight right
184 ft·8 sec
9
Continue on East Lombard Street
1.3 mi·2 min·East Lombard Street
Use the left / straight / right lanes.
10
Turn left onto MD 150
0.1 mi·28 sec·Ponca Street
11
Take the ramp
0.3 mi·36 sec
Toward I 895 Toll South
12
Merge onto I 895
1.8 mi·2 min·Harbor Tunnel Thruway
13
Continue on I 895
1.4 mi·2 min·Baltimore Harbor Tunnel
14
Continue on I 895
2.2 mi·3 min·Harbor Tunnel Thruway
Use the straight / slight right lanes.
15
Continue on I 895
0.5 mi·39 sec·Harbor Tunnel Throughway
16
Keep slight right at fork onto Harbor Tunnel Throughway
1.7 mi·2 min·Harbor Tunnel Throughway
Exit 6Toward Annapolis, Glen BurnieUse the straight / slight right lanes.
17
Keep slight left at fork onto Harbor Tunnel Throughway
1.2 mi·1 min·Harbor Tunnel Throughway
Use the straight / slight right lanes.
18
Turn straight onto MD 2
1.2 mi·2 min·Ritchie Highway
19
Turn left onto MD 270
0.4 mi·36 sec·East Furnace Branch Road
Use the straight / left lanes.
20
Take the ramp
0.3 mi·44 sec
Toward MD 10 South
21
Merge onto MD 10
4.0 mi·5 min·Arundel Expressway
Use the straight lane.
22
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.
23
Turn left onto MD 2
2.4 mi·3 min·Ritchie Highway
24
Continue on MD 2
6.1 mi·8 min·Governor Ritchie Highway
Use the straight lane.
25
Take the exit
0.2 mi·22 sec
Toward US 50 East, US 301 North: Bay Bridge
26
Merge onto US 50; US 301
19 mi·27 min·Blue Star Memorial Highway
Use the straight / slight right lanes.
27
Keep slight left at fork onto US 301
5.7 mi·8 min·Blue Star Memorial Highway
Toward US 301 North
28
Take the exit
0.3 mi·49 sec
Toward MD 213 North
29
Turn straight onto MD 213
2.0 mi·3 min·Centreville Road
30
Continue on MD 213
0.6 mi·1 min·South Commerce Street
31
Continue on MD 213
15 mi·22 min·Church Hill Road
32
Continue on MD 213
0.1 mi·13 sec·Chestertown Church Hill Road
33
Continue on MD 213
0.2 mi·27 sec·Maple Avenue
34
Turn left onto MD 289
0.1 mi·22 sec·North Cross Street
35
Arrive at destination
MD 289
Trip Plan
With a drive time under two hours, this route is ideal for a same-day trip, giving you flexibility with your departure time. Consider leaving mid-morning to avoid the heaviest rush hour traffic. Since it's a short drive with no designated stops, you can easily plan for a quick break if needed, perhaps in Church Hill. Keep an eye on your fuel gauge, as the estimated cost is around $12, and it's wise to top off before you leave Essex to ensure a smooth, uninterrupted drive to Chestertown.
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 36.3 miles from Essex, MD, or about 57m into the drive.
The longest continuous stretch on this route runs about 24.8 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 16 miles or 28m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 36.3 miles or 57m 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 34m
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 Essex, MD so your first major turns are already loaded.
Day 1
Settle into the route from Essex, MD
This is one driving day of about 72.5 miles and 1h 50m.
Your first comfortable stop window is around 16 miles from Essex, MD.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on Blue Star Memorial Highway for about 24.8 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 0.1 and 19.9 — 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
Turn left
Navigation decision point
5
0.1 mi into trip|~0m in|MD 150 / Eastern Boulevard
At end of road, turn right onto MD 150 / Eastern Boulevard
Navigation decision point
9
11.1 mi into trip|~20m in|Harbor Tunnel Throughway
Keep slight right at fork onto Harbor Tunnel Throughway toward Annapolis, Glen Burnie
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 6
Toward Annapolis, Glen Burnie
6
12.7 mi into trip|~22m in|Harbor Tunnel Throughway
Keep slight left at fork onto Harbor Tunnel Throughway
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
7
19.9 mi into trip|~33m 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
$12.02 one way
$24.04 round trip
$4.21/gal25.4 MPG avg25 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.61
$13.16
$26.33
premium
$4.93
$14.06
$28.12
diesel
$5.61
$16.01
$32.01
Estimated Tolls: $0.28
Harbor Tunnel Thruway
(4 mi)$0.28
Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.
Estimated Trip Cost (one way, 1 person)
Fuel
$12
Tolls
$0
Meals
$25–$50
Total
$37–$62
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 25.4 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $8 in charging
· 0 stops
· 68% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
21.8
0
$7.61
$3.48
Efficient EV
18.1
0
$6.34
$2.90
EV Truck/SUV
29
0
$10.15
$4.64
Gas CO2
25 kg
EV CO2
8 kg (68% 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
Essex, MD
Late night
in Essex on Tuesday
Local time
5:42 AM
EDT
Current temp
64°F
Unavailable
Live forecast
Destination
Chestertown, MD
Late night
in Chestertown on Tuesday
Local time
5:42 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
15 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 50m 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?
This route is primarily surface roads, with only about 6% of the drive on highways. You'll experience 24.8 miles on the Blue Star Memorial Highway before transitioning to local roads like Church Hill Road and Governor Ritchie Highway. Be prepared for frequent intersections and traffic signals as you move from highway cruising to navigating through towns and local communities.
Only 6% highway — the rest is turn-by-turn surface driving.
35 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 24.8 mi on Blue Star Memorial Highway.
How Hard Is This Drive?
10/10
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 0.1 miles in.
Driving Effort10/10
Demanding - stay alert through the decision-heavy sections
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 72.5 miles you will encounter 17 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: Navigation decision point; at 0.1 miles (MD 150 / Eastern Boulevard): Navigation decision point; at 11.1 miles (Harbor Tunnel Throughway): Highway fork - watch signs carefully. 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 Essex, MD and Chestertown, MD, road signs point toward Annapolis and Glen Burnie.
Southeast Baltimore, fittingly, covers the areas in the southeast of Baltimore, ranging from industrial wastelands to charming neighborhoods both quiet and hip.
Doable as a same-day drive at 1h 50m. Total distance: 72.5 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 50m drive, comfortable solo distance.
Scenic Drive
Mostly surface roads route profile.
Frequently Asked Questions
The longest stretch is about 24.8 miles on Blue Star Memorial Highway. The full list of main roads is in the Roads section above.
Expect about $0.28 in tolls one way, starting with Harbor Tunnel Thruway. Most Northeast and Midwest toll agencies accept E-ZPass; in the West and Texas, transponders like TxTag or FasTrak apply. If you do not have a transponder, cashless tolling plates will mail a bill to the vehicle's registered address — usually with a surcharge, so a rental-car toll pass is often cheaper than paying by mail.
Yes — we found about 2 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.
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: Navigation decision point; at 0.1 miles (MD 150 / Eastern Boulevard): Navigation decision point; at 11.1 miles (Harbor Tunnel Throughway): Highway fork - watch signs carefully. 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.
