How far is Redland, MD from Chestertown, MD?
The driving distance from Redland, MD to Chestertown, MD is about 89.8 miles (144.5 km), with a travel time of about 02h 08m by car.
- The straight-line flight distance is about 57.9 miles (93.2 km).
- For a round trip, plan for roughly 04h 17m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 02h 08m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
You are leaving earlier than the recommended window, which gives you extra margin for breaks and traffic.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
City in and county seat of Anne Arundel County, Maryland, United States, and Maryland federated state capital city
Route Weather Snapshot
Check the forecast at both ends before you head out.
Chance Rain Showers
Chance Rain Showers then Mostly Cloudy
Driving Route Map
The map below follows the saved road route between Redland and Chestertown.
Turn-by-Turn Driving Directions
Step-by-step road directions between Redland and Chestertown.
-
1
Start on Redland Road
29 m · 8 sec · Redland Road
-
2
Turn right onto Muncaster Mill Road
4.5 mi · 9 min · Muncaster Mill Road
-
3
Turn left onto Norbeck Road
1179 ft · 29 sec · Norbeck Road
-
4
Turn left onto Georgia Avenue
1525 ft · 38 sec · Georgia Avenue
-
5
Take the ramp slight right toward MD 200 Toll East
2675 ft · 1 min
-
6
Merge slight left onto Intercounty Connector
4.4 mi · 5 min · Intercounty Connector
-
7
Take the exit slight right toward MD 650: Ashton, White Oak
1269 ft · 31 sec
-
8
Keep slight right to continue on MD 650 South: White Oak
110 m · 9 sec
-
9
Turn straight onto New Hampshire Avenue
5.1 mi · 9 min · New Hampshire Avenue
-
10
Take the ramp slight right toward I 495 East: Baltimore, College Park
1019 ft · 25 sec
-
11
Merge slight left onto Capital Beltway
8.8 mi · 11 min · Capital Beltway
-
12
Take the exit slight right toward US 50 East: Annapolis
1 mi · 2 min
-
13
Merge slight left onto John Hanson Highway
18.7 mi · 22 min · John Hanson Highway
-
14
Continue on Blue Star Memorial Highway
21.6 mi · 30 min · Blue Star Memorial Highway
-
15
Keep slight left to continue on Blue Star Memorial Highway
5.7 mi · 8 min · Blue Star Memorial Highway
-
16
Take the exit slight right toward MD 213 North
1814 ft · 50 sec
-
17
Turn straight onto Centreville Road
2 mi · 3 min · Centreville Road
-
18
Continue on South Commerce Street
1 km · 1 min · South Commerce Street
-
19
Continue on Church Hill Road
14.9 mi · 22 min · Church Hill Road
-
20
Continue on Chestertown Church Hill Road
773 ft · 13 sec · Chestertown Church Hill Road
-
21
Continue on Maple Avenue
1196 ft · 28 sec · Maple Avenue
-
22
Turn left onto North Cross Street
770 ft · 23 sec · North Cross Street
-
23
Arrive at your destination
0 m · 1 sec · South Cross Street
Car Route Details
A richer read on the saved driving route between Redland and Chestertown.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
Blue Star Memorial Highway
Continue on Blue Star Memorial Highway
21.6 mi · 00h 30m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Chance Rain Showers leaving Redland and Chance Rain Showers then Mostly Cloudy near Chestertown.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Redland to Chestertown?
The road trip is about 89.8 miles (144.5 km) and usually takes 02h 08m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Annapolis is a useful midpoint, sitting about 44.8 miles from Redland and 45 miles from Chestertown.
How much longer is the road route than the straight-line distance?
The direct path is about 57.9 miles (93.2 km), while the road route adds roughly 31.9 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 2:12 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $13.39 one way or $26.77 round trip. Estimated CO2 is about 28.2 kg one way.
What should you check before leaving?
Before you leave, expect Chance Rain Showers around Redland and Chance Rain Showers then Mostly Cloudy near Chestertown.
Stop Ideas Near Annapolis
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
City of Bowie
Annapolis City Hall
Kenhill Center
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Annapolis.
Kent Island, MD
BWI Rail Station
New Carrollton station
Pennsylvania Station
Flight Path Map
This map shows the direct air route between Redland and Chestertown. Straight-line distance: 57.88 mi (93.15 km).
#1 Redland
A census-designated place in Prince George's County, Maryland.
| Population | 147,010 |
| Coordinates | 39.1453900, -77.1441500 |
| Altitude | 150 |
| Country | United States |
#2 Chestertown
Town in Maryland, United States
| Population | 5,001 |
| Coordinates | 39.2090000, -76.0666100 |
| Altitude | 4 |
| Country | United States |
End: Chestertown (-76.06661, 39.209)
Estimated Travel Time
Distance: 144 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 59m |
| 40 mph (64.37 km/h) | 02h 14m |
| 50 mph (80.47 km/h) | 01h 47m |
| 60 mph (96.56 km/h) | 01h 29m |
| 70 mph (112.65 km/h) | 01h 16m |
| 80 mph (129 km/h) | 01h 07m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.22 | $13.39 | $26.77 |
| Mid-grade | $4.84 | $15.35 | $30.70 |
| Premium | $5.17 | $16.40 | $32.80 |
| Diesel | $6.49 | $20.58 | $41.15 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in Maryland · Sep 22, 2026