Origin
Chester, VT
Late night in Chester on Sunday
Local time
12:35 AM
EDT
Current temp
37°F
Unavailable
Live forecast
Trip from Chester, VT to Brattleboro, VT
Compiled and reviewed by the US Trip Planner planning team at COD Solutions Oy · Last reviewed Apr 19, 2026 · Editorial standards
Drive Time
51m
Distance
37.3 mi
60 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$6
one way
EV Charging
Unknown
Best Time to Leave
4 AM
0h 47m
★
6 AM
0h 51m
8 AM
1h 0m
10 AM
0h 54m
12 PM
0h 53m
3 PM
0h 55m
5 PM
0h 59m
8 PM
0h 49m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Chester, VT
Wikimedia Commons
Brattleboro, VT
Wikimedia Commons
Trip Overview
If you are planning to travel from Chester to Brattleboro, you can expect a straightforward, 37.3-mile journey through Vermont. Clocking in at approximately 51 minutes, this trip is perfectly suited as a quick day trip that requires no overnight stay. You will primarily navigate via Vermont Route 103 South, Rockingham Road, and I-91. Budgeting around $6 for fuel should cover your transit costs comfortably. Since both the origin and destination are located within the Northeast region, you will experience the classic character of the Vermont landscape throughout the entire drive. It is a practical, efficient connection that gets you from point A to point B without any unnecessary complexity.
Main Roads
| Road | Distance | Duration |
|---|---|---|
| I 91 | 25.8 mi | 29m |
| Rockingham Road | 6.3 mi | 9m |
| Vermont Route 103 South | 2.5 mi | 4m |
| Western Avenue | 0.7 mi | 1m |
| South Main Street | 0.5 mi | 1m |
| High Street | 0.4 mi | 1m |
| Main Street | 0.2 mi | <1m |
| Grafton Street | <0.1 mi | <1m |
Longest stretch:
I 91
— 25.8 mi, about 29m
Turn-by-Turn Driving Directions
Step-by-step road directions between Chester, VT and Brattleboro, VT.
1
Start on VT 35
72 ft
·
7 sec
·
Grafton Street
2
Turn right onto VT 11
0.5 mi
·
1 min
·
South Main Street
3
Continue on VT 103
2.5 mi
·
4 min
·
Vermont Route 103 South
4
Continue on VT 103
6.3 mi
·
9 min
·
Rockingham Road
5
Take the exit
0.4 mi
·
51 sec
Toward I 91 South: Brattleboro
6
Merge onto I 91
26 mi
·
29 min
·
I 91
7
Take the exit
0.5 mi
·
1 min
Exit 2
Toward VT 9 West: Brattleboro, Bennington
8
At end of road, turn left onto VT 9
0.7 mi
·
1 min
·
Western Avenue
9
Continue on VT 9
0.4 mi
·
1 min
·
High Street
10
At end of road, turn right onto US 5
0.2 mi
·
38 sec
·
Main Street
11
At end of road, turn right onto US 5
54 ft
·
1 sec
·
Canal Street
12
Turn right
110 ft
·
8 sec
13
Arrive at destination
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Mid-route town
Meal stop
19 mi into the route
Best for: Lunch, fuel, and a longer reset
This sits close to the middle of the route, so it works well for the longest stop of the day.
Pacing Suggestions
Fuel and coffee
A short stop after about 37 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 18.7 miles from Chester, VT, which is a good place for a longer meal and fuel stop.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Heads-up: tricky spots
5 of 85 decision points cluster between mile 0 and 37.3 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
4
0 mi into trip
|
~0m in
|
VT 11 / South Main Street
Turn right onto VT 11 / South Main Street
Navigation decision point
4
9.2 mi into trip
|
~15m in
Take the exit toward I 91 South: Brattleboro
Exit ramp - move to the correct lane early
Toward I 91 South: Brattleboro
6
35.5 mi into trip
|
~46m in
Take the exit toward VT 9 West: Brattleboro, Bennington
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Exit 2
Toward VT 9 West: Brattleboro, Bennington
4
37.1 mi into trip
|
~50m in
|
US 5 / Main Street
At end of road, turn right onto US 5 / Main Street
Navigation decision point
5
37.3 mi into trip
|
~51m in
|
US 5 / Canal Street
At end of road, turn right onto US 5 / Canal Street
Navigation decision point
Fuel & Cost
Regular Gas
$6.00 one way
$12.01 round trip
$4.09/gal
25.4 MPG avg
13 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.50 | $6.61 | $13.21 |
| premium | $4.86 | $7.14 | $14.29 |
| diesel | $5.61 | $8.24 | $16.47 |
No toll roads detected on this route.
Drive Cost (one way)
Fuel
$6
Estimated CO2 emission: 13.1 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $4 in charging · 0 stops · 69% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 11.2 | 0 | $3.92 | $1.79 |
| Efficient EV | 9.3 | 0 | $3.26 | $1.49 |
| EV Truck/SUV | 14.9 | 0 | $5.22 | $2.39 |
Gas CO2
13 kg
EV CO2
4 kg (69% 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.
Destination
Brattleboro, VT
Late night in Brattleboro on Sunday
Local time
12:35 AM
EDT
Current temp
45°F
Unavailable
Live forecast
35°F
Westminster, VT
19 mi in
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
8 degrees warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
51m 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.
What kind of drive is this?
This route is defined by a highway-focused profile, with 76% of your time spent on major roads. You will settle into a steady rhythm on I-91, which accounts for the longest uninterrupted stretch of 25.8 miles. While the start of your journey involves local roads like Rockingham Road and Route 103, the experience quickly transitions into an interstate drive. Behind the wheel, you will notice the shift from regional connectors to the faster pace of the highway. Expect a consistent and predictable drive that prioritizes speed and efficiency over winding backroads.
76% highway — fuel and pacing are the main things to plan.
13 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 25.8 mi on I 91.
How Hard Is This Drive?
4/10
This is a straightforward highway drive that stays mostly on I 91 and Rockingham Road. There are only a few real navigation decisions along the way. The trickiest moment comes early in the drive near VT 11 / South Main Street.
Driving Effort
4/10
Easy - simple navigation with a manageable amount of wheel time
Balances navigation complexity with total wheel time.
This is a straightforward 51m drive. You will face about 8 decision points, but nothing that requires special attention if you follow navigation.
Where does it get tricky?
The main spots that need attention: near the start (VT 11 / South Main Street): Navigation decision point; at 9.2 miles: Exit ramp - move to the correct lane early; at 35.5 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 51m. Total distance: 37.3 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
51m drive, comfortable solo distance.
EV Driver
0 DC fast chargers along the route. Coverage: unknown.
First-Time Driver
Mostly highway driving (76%). Straightforward navigation.
Frequently Asked Questions
The longest stretch is about 25.8 miles on I 91. The full list of main roads is in the Roads section above.
Yes. At under 2 hours behind the wheel, this works well for families — plan one quick stop if you have younger kids.
Mostly yes along the main roads, but rural stretches through VT can have sparse or no coverage. Before you leave, download offline Google Maps or Apple Maps for the route, and consider downloading music or podcasts instead of streaming. If you depend on data for navigation, keep a paper backup of the turn-by-turn directions.
The main spots that need attention: near the start (VT 11 / South Main Street): Navigation decision point; at 9.2 miles: Exit ramp - move to the correct lane early; at 35.5 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Yes. A round trip is manageable in a single day if you plan a break at Brattleboro, VT before heading back.
How this page is built
Compiled by the US Trip Planner planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, and EIA for fuel prices. See our methodology for refresh cadence and limitations.
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