How far is Chester, VT from Bennington, VT?
The driving distance from Chester, VT to Bennington, VT is about 52 miles (83.7 km), with a travel time of about 01h 05m by car.
- The straight-line flight distance is about 40.4 miles (65 km).
- For a round trip, plan for roughly 02h 10m 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 01h 05m.
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.
Route Weather Snapshot
Check the forecast at both ends before you head out.
Slight Chance Snow Showers then Mostly Cloudy
Slight Chance Rain Showers then Partly Sunny
Driving Route Map
The map below follows the saved road route between Chester and Bennington.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chester and Bennington.
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1
Start on Grafton Street
22 m · 7 sec · Grafton Street
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2
Turn left onto Main Street
1.2 km · 2 min · Main Street
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3
Continue on Vermont Route 11 West
4.4 mi · 7 min · Vermont Route 11 West
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4
Continue on Simonsville Road
3.7 mi · 6 min · Simonsville Road
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5
Continue on Vermont Route 11
5.6 mi · 9 min · Vermont Route 11
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6
Continue on North Main Street
2077 ft · 59 sec · North Main Street
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7
Continue on Vermont Route 11
11.5 mi · 18 min · Vermont Route 11
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8
Continue on Depot Street
1.3 mi · 2 min · Depot Street
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9
Continue on Depot Street
2654 ft · 56 sec · Depot Street
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10
Take the ramp slight right toward US 7 South: Bennington
1442 ft · 40 sec
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11
Merge slight left onto U.S. Route 7
21.6 mi · 29 min · U.S. Route 7
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12
Merge slight right onto Bennington Bypass
953 ft · 15 sec · Bennington Bypass
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13
Keep slight right to continue on U.S. Route 7
1.5 km · 2 min · U.S. Route 7
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14
Continue on North Street
1791 ft · 48 sec · North Street
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15
Turn right onto Depot Street
2369 ft · 1 min · Depot Street
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16
Turn left onto Main Street
754 ft · 23 sec · Main Street
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17
Arrive at your destination
0 m · 1 sec · Main Street
Car Route Details
A richer read on the saved driving route between Chester and Bennington.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
U.S. Route 7
Merge slight left onto U.S. Route 7
21.6 mi · 00h 29m
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.
Slight Chance Snow Showers then Mostly Cloudy leaving Chester and Slight Chance Rain Showers then Partly Sunny near Bennington.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chester to Bennington?
The road trip is about 52 miles (83.7 km) and usually takes 01h 05m 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?
Manchester is a useful midpoint, sitting about 26 miles from Chester and 26 miles from Bennington.
How much longer is the road route than the straight-line distance?
The direct path is about 40.4 miles (65 km), while the road route adds roughly 11.6 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 4:20 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $7.26 one way or $14.52 round trip. Estimated CO2 is about 16.4 kg one way.
What should you check before leaving?
Before you leave, expect Slight Chance Snow Showers then Mostly Cloudy around Chester and Slight Chance Rain Showers then Partly Sunny near Bennington.
Stop Ideas Near Manchester
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Manchester.
Okemo, Vermont
Fort Edward station
Fair Haven, Vermont
Rutland station
Flight Path Map
This map shows the direct air route between Chester and Bennington. Straight-line distance: 40.36 mi (64.95 km).
#1 Chester
Town in Windsor County, Vermont, United States
| Population | 3,018 |
| Coordinates | 43.2628500, -72.5950900 |
| Altitude | 185 |
| Country | United States |
#2 Bennington
Town in Vermont, United States
| Population | 14,897 |
| Coordinates | 42.8781300, -73.1967700 |
| Altitude | 207 |
| Country | United States |
End: Main Street (-73.196743, 42.878279)
Estimated Travel Time
Distance: 84 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 43m |
| 40 mph (64.37 km/h) | 01h 18m |
| 50 mph (80.47 km/h) | 01h 02m |
| 60 mph (96.56 km/h) | 00h 52m |
| 70 mph (112.65 km/h) | 00h 44m |
| 80 mph (129 km/h) | 00h 38m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $7.26 | $14.52 |
| Mid-grade | $4.46 | $8.20 | $16.40 |
| Premium | $4.86 | $8.94 | $17.88 |
| Diesel | $6.00 | $11.03 | $22.07 |
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 Vermont · Apr 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.