How to Spend a Weekend in Chester, Vermont

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We were getting antsy in the summer so we decided to do a mini road trip with our friends to Vermont! Gabi and I has both been before, but never to the area, Chester, where we were staying. Vermont is known as the Green Mountain State because of, well, a big green mountain in the middle of it lol. There are a lot of outdoor activities you can do here & a lot of local beer to drink! Vermont is known for it’s winter activities but we totally had a blast here in the summer and would definitely recommend it if you want a nice nature getaway.

How to get to Vermont

We drove to Vermont and it took about 5 hours. It was a nice smooth ride and you will definitely need a car to get around the state. Nothing is really in walking distance and a car give you the freedom to do what you want whenever you want to!

Where to Stay

We stayed at an Airbnb and that’s probably the best option in Chester. Yes there are some hotels, but for this kind of trip, having a house in the mountains away from all the noise is probably exactly what you’re looking for. Our Airbnb was in a great location and for a bunch of city people, we all felt very safe in our cabin in the woods.

Best Things to Do

  • Go hiking at Mount Ascutney

  • Explore the town of Ludlow

  • Walk the abandoned train tracks in Proctorsville

  • Get some shopping done at the Vermont Country Store

  • Walk around Lowell State Park

  • Try some local brews at Long Trail Brewery

  • Explore some abandoned buildings in Chester

  • Try some local Vermont maple syrup

  • Just drive around aimlessly & get lost

Where to Eat & Drink

  • The Pizza Stone

  • The Hatchery

  • Long Trail Brewery

  • Crows Bakery

Vermont is great place for a weekend getaway, away from all the hustle and bustle of NYC life. We relaxed, got to enjoy nature, and play lots of board games with our friends. We also vlogged our entire trip so if you want see more of all the areas we visited check out our video below!


Exploring the Green Mountain State

We drove up to Vermont for the weekend and has the best time exploring the Green Mountain State with our bffs Rob & Ameed! We hiked to a waterfall at Mount Ascutney, drank delicious beer at Long Trail Brewery, and took a splash in Lake Lowell.