OffBeat Pathfinder Basecamp

Arriving in Chester is like walking straight into a New England postcard—and then realizing you can actually stay there. I came for the covered bridges, but the “cozy” factor nearly sent me into hibernation.


**Covered Bridges:**
First stop: The Stone Village. Blink and you’ll miss it, but it’s worth a U-turn for the granite houses alone. Vermont’s famous for its covered bridges, and Chester has some of the most photogenic. The Worrall Covered Bridge looks like it was built for Instagram, especially at dawn with the mist on the river.


The Bartonsville Covered Bridge? Classic red, rebuilt after Hurricane Irene, and now so sturdy it probably survived a few maple syrup floods since. If you’re a bridge nerd (no shame), this is paradise. Locals love to swap stories about ghostly carriages and wild raccoons—just ask at the country store.


**Village Strolls & General Store Lore:**
Chester Green is the beating heart of the village. Antique shops, indie bookstores, bakeries—pick your vice. I lost an hour in Misty Valley Books (and $32 to Vermont history I’ll never use). The Country Girl Diner still serves pancakes as big as your head, and if you get lucky, there’s a bluegrass picker on the porch.


**Cozy Vibes & Maple Everything:**
I stayed at a tiny B&B where the owner greeted me with homemade maple cookies and a tour of her backyard chicken coop. Evenings here mean firepits, neighbor dogs, and someone inevitably telling you about that time they “almost saw a moose.”


Don’t skip the Chester Fall Festival if you’re in town—folks come from miles around for crafts, apple cider, and a pie contest so cutthroat I saw a grandma get side-eyed for using store-bought crust.


Pro tip: Pick up real Vermont maple syrup (accept no imitations). I brought home a half-gallon and have since put it on toast, oatmeal, and, in a moment of weakness, spaghetti.


**Bridges, Baked Goods, and Small-Town Magic:**
Anyone else have a favorite bridge or bakery? Or is there a secret Chester hangout I missed?


Drop your best Chester stories below—bonus points for anything involving snowstorms or maple syrup emergencies!

Caught the Friday night jam session at Country Girl Diner—locals sure know how to make bluegrass and pancakes go together. Best coffee in town.

Stayed at a dog-friendly cabin just outside Chester. My retriever got more attention than I did—Vermonters love their dogs!

Chester Fall Festival = the best pie I’ve ever eaten, full stop. If you get there early, bring elbow pads for the dessert line.

Maple syrup on everything. Yes, even pizza. Don’t judge it till you’ve tried it!

Walked across the Bartonsville bridge during a snowstorm—looked like something out of a Hallmark movie. Slipped on the way back but kept my hot cocoa upright. #priorities

Heard rumors about northern lights being visible from Chester. I saw lots of Christmas lights, does that count?

Drove up from Massachusetts for the weekend—left with Vermont cheddar, maple candy, and a strong desire to move into a covered bridge.