Chester, VT Road Trips

Drivers starting from Chester, VT have 11 mapped routes to choose from, making it a small but connected base in the Northeast. Most drives stay under 96 miles, making this area well-suited for day trips and weekend getaways. Most routes from Chester, VT head north, giving the route network a clear directional lean.

town in Windsor County, Vermont, United States

Photo: Wikimedia Commons

Trip Routes

17

Longest Drive

142.2 mi

Milton, VT

Quickest Drive

16m

Springfield, VT

Plan Around Chester, VT

Popular Incoming Routes

Useful if Chester, VT is the arrival point and you want the strongest routes into the city first.

Burlington, VT to Chester, VT 133.8 mi · 2h 43m Montpelier, VT to Chester, VT 98.6 mi · 2h Bennington, VT to Chester, VT 51.6 mi · 1h 18m Hartford, VT to Chester, VT 47 mi · 1h 1m

Continue From Chester, VT

Good next legs if this city is only one stop in a longer road trip.

Chester, VT to Milton, VT 142.2 mi · 3h 2m Chester, VT to Colchester, VT 135 mi · 2h 47m Chester, VT to South Burlington, VT 133.3 mi · 2h 41m Chester, VT to Essex Junction, VT 131.5 mi · 2h 40m

Trips from Chester, VT

Chester, VT to Milton, VT

142.2 mi 3h 2m

Chester, VT to Colchester, VT

135 mi 2h 47m

Chester, VT to South Burlington, VT

133.3 mi 2h 41m

Chester, VT to Essex Junction, VT

131.5 mi 2h 40m

Chester, VT to Williston, VT

125.6 mi 2h 32m

Chester, VT to St Johnsbury, VT

104.8 mi 2h 7m

Chester, VT to Montpelier, VT

98.4 mi 2h

Chester, VT to Shelburne, VT

97 mi 2h 35m

Chester, VT to Hartford, VT

46.5 mi 1h

Chester, VT to Brattleboro, VT

37.3 mi 51m

Chester, VT to Springfield, VT

8 mi 16m

Driving from Chester, VT

Expect an average of 96 miles and about 2h 3m behind the wheel when leaving Chester, VT. The majority of routes are short drives — quick enough to finish before lunch and be back for dinner. The longest mapped route runs 142 miles (3h 2m), while the shortest is just 8 miles.

Popular Destinations

Top road trip destinations from Chester, VT are Milton, VT (142.2 mi, 3h 2m), Colchester, VT (135 mi, 2h 47m), South Burlington, VT (133.3 mi, 2h 41m), Essex Junction, VT (131.5 mi, 2h 40m), and Williston, VT (125.6 mi, 2h 32m). Most destinations stay within the same state, perfect for exploring the local region thoroughly.

Planning & Costs

Regular gas in VT currently averages around $3.95 per gallon. For the typical 96-mile trip from Chester, VT, budget about $15 in fuel one way, assuming 25 MPG. Longer hauls and premium fuel will cost proportionally more.

Routes mostly head north. Summer trips benefit from long daylight hours, while winter departures should start early to maximize visibility. With an average drive under three hours, you have plenty of flexibility — leave whenever it suits you.

Frequently Asked Questions

There are 11 mapped routes leaving Chester, VT and 6 routes heading into Chester, VT, covering 17 total connections. Distances range from 8 to 142 miles.

The longest mapped route from Chester, VT covers 142 miles and takes approximately 3h 2m. Shorter options start at just 8 miles.

The average route from Chester, VT runs about 96 miles with a drive time of roughly 2h 3m. This includes both short day trips and longer multi-day drives.

At current gas prices (about $3.95/gallon for regular), the average 96-mile trip from Chester, VT costs roughly $15 in fuel one way, based on 25 MPG. Your actual cost depends on your vehicle's efficiency.

The most popular road trip destinations from Chester, VT include Milton, VT, Colchester, VT, South Burlington, VT and Essex Junction, VT. Each route page has detailed drive times, fuel estimates, stop suggestions, and turn-by-turn directions.