How far is Middlesex, VT from Bennington, VT?
The driving distance from Middlesex, VT to Bennington, VT is about 126.3 miles (203.3 km), with a travel time of about 03h 03m by car.
- The straight-line flight distance is about 101.1 miles (162.7 km).
- For a round trip, plan for roughly 06h 06m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 AM EDT.
Reverse, save, or send this route
This drive is better planned with a longer stop or an overnight stay. Copy the route link, send it to another device, or print a clean version before you head out.
This drive is better planned with a longer stop or an overnight stay.
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 03h 03m.
An early departure helps you fit a real stop into the day without turning the return into a late-night drive.
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.
Town in Rutland County, Vermont, USA
Route Weather Snapshot
Check the forecast at both ends before you head out.
Partly Sunny
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Middlesex and Bennington.
Turn-by-Turn Driving Directions
Step-by-step road directions between Middlesex and Bennington.
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1
Start on U.S. Route 2
2409 ft · 56 sec · U.S. Route 2
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2
Turn slight right
44 m · 6 sec
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3
Turn straight onto Center Road
73 m · 6 sec · Center Road
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4
Take the ramp right
877 ft · 21 sec
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5
Merge slight left
36.2 mi · 42 min
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6
Take the exit slight right toward VT 107: Bethel, Royalton
1570 ft · 47 sec
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7
Turn right onto Vermont Route 107
1.7 mi · 3 min · Vermont Route 107
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8
Continue on South Main Street
1.4 km · 2 min · South Main Street
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9
Turn slight left onto River Street
3.4 mi · 6 min · River Street
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10
Continue on Vermont Route 107
6.7 mi · 10 min · Vermont Route 107
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11
Continue on Vermont Route 100
10.7 mi · 16 min · Vermont Route 100
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12
Merge slight left onto U.S. Route 4
9.3 mi · 15 min · U.S. Route 4
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13
Continue on Woodstock Avenue
1.2 mi · 3 min · Woodstock Avenue
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14
At the end of the road, turn left onto North Main Street
53.1 mi · 1 hr 20 min · North Main Street
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15
Merge slight right onto Bennington Bypass
953 ft · 15 sec · Bennington Bypass
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16
Keep slight right to continue on U.S. Route 7
1.5 km · 2 min · U.S. Route 7
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17
Continue on North Street
1791 ft · 48 sec · North Street
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18
Turn right onto Depot Street
2369 ft · 1 min · Depot Street
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19
Turn left onto Main Street
754 ft · 23 sec · Main Street
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20
Arrive at your destination
0 m · 1 sec · Main Street
Car Route Details
A richer read on the saved driving route between Middlesex and Bennington.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
North Main Street
At the end of the road, turn left onto North Main Street
53.1 mi · 01h 20m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A longer out-and-back drive
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
Partly Sunny leaving Middlesex and Mostly Sunny near Bennington.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Middlesex to Bennington?
The road trip is about 126.3 miles (203.3 km) and usually takes 03h 03m in normal driving conditions.
Is this a same-day trip or an overnight route?
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
What is the halfway point on this route?
Killington is a useful midpoint, sitting about 63.2 miles from Middlesex and 63.2 miles from Bennington.
How much longer is the road route than the straight-line distance?
The direct path is about 101.1 miles (162.7 km), while the road route adds roughly 25.2 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 6:00 AM to 8:00 AM EDT. If you want a more comfortable same-day return, try to leave by 10:54 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $17.59 one way or $35.19 round trip. Estimated CO2 is about 39.6 kg one way.
What should you check before leaving?
Before you leave, expect Partly Sunny around Middlesex and Mostly Sunny near Bennington.
Stop Ideas Near Killington
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 Killington.
Rutland station
Randolph station
Okemo, Vermont
Castleton station
Flight Path Map
This map shows the direct air route between Middlesex and Bennington. Straight-line distance: 101.12 mi (162.74 km).
#1 Middlesex
Town in Washington County, Vermont, United States of America
| Population | 1,724 |
| Coordinates | 44.2928400, -72.6792800 |
| Altitude | 161 |
| Country | United States |
#2 Bennington
Town in Vermont, United States
| Population | 14,897 |
| Coordinates | 42.8781300, -73.1967700 |
| Altitude | 207 |
| Country | United States |
End: Bennington (-73.19677, 42.87813)
Estimated Travel Time
Distance: 203 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 04h 12m |
| 40 mph (64.37 km/h) | 03h 09m |
| 50 mph (80.47 km/h) | 02h 31m |
| 60 mph (96.56 km/h) | 02h 06m |
| 70 mph (112.65 km/h) | 01h 48m |
| 80 mph (129 km/h) | 01h 34m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $17.59 | $35.19 |
| Mid-grade | $4.46 | $19.88 | $39.76 |
| Premium | $4.86 | $21.67 | $43.33 |
| Diesel | $6.00 | $26.75 | $53.49 |
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.