I Hit Vermont’s Back Roads To Sample 10 Cheddar Grilled Cheeses (And 4 Totally Delivered)
Cruising Vermont’s back roads, I discovered a hidden world of cheddar grilled cheese that goes far beyond the ordinary.
From gooey, perfectly melted layers to inventive twists that surprise with every bite, some sandwiches were unforgettable.
Four of them stood out, delivering flavors that made the detours completely worth it.
Each stop offered a little taste of Vermont’s cheesemaking magic, proving that sometimes the simplest comfort food can become a true culinary adventure.
1. Wayside Restaurant & Bakery — Montpelier
Wayside is a Montpelier institution, the kind of place where politicians and construction workers eat side by side. Their grilled cheese is straightforward: cheddar, butter, bread, griddle.
Unfortunately, the cheese tasted a bit bland, like they skimped on the aging process. The bread was fine but unremarkable, and the whole thing felt like it was made on autopilot.
It fills you up, sure, but you won’t be telling your friends about it over beers later.
2. Handy’s Lunch — Burlington
Handy’s Lunch in Burlington is a family-run diner that’s been serving comfort food since 1945. Located on Maple Street, it’s known for its classic horseshoe counter, warm service, and nostalgic charm.
Locals and visitors crowd in for hearty breakfasts, stacked sandwiches, and the famous “Texas dog”, a chili-topped hot dog that’s become a local legend.
The atmosphere feels like stepping back in time, where every plate comes with a side of community and tradition.
3. Putney General Store — Putney
Putney General Store has that old-school charm where locals gossip over coffee and tourists buy maple syrup by the gallon. Their grilled cheese is no-frills, made with standard cheddar on white bread.
It’s decent, warm, and filling, but nothing about it makes you want to write home. The cheese barely stretches, and the bread lacks that buttery crispness.
Great for a quick bite if you’re passing through, but it won’t haunt your dreams or earn a spot on your must-visit list.
4. Otter Creek Bakery & Deli — Middlebury
Otter Creek Bakery smells like heaven, with fresh bread and pastries lining the shelves. Their grilled cheese uses house-baked bread, which should be a slam dunk.
Sadly, the execution fell flat. The cheese was mild and forgettable, and the bread, while fresh, was too thick and doughy.
It felt more like a cheese-stuffed roll than a proper grilled cheese. You leave full but not satisfied, wishing they had nailed the balance between bread and cheese better.
5. Blue Benn Diner — Bennington
Blue Benn Diner is a 1950s time capsule with turquoise booths and a jukebox that still works. Their grilled cheese is classic diner style, nothing fancy, just cheese and bread on the griddle.
It tasted fine but totally forgettable. The cheese was mild, the bread was standard white, and the whole thing lacked personality.
You eat it, you move on, and you forget about it by the time you hit the highway. Not bad, just painfully average.
6. Henry’s Diner — Burlington
Henry’s Diner has been a Burlington breakfast staple since 1925, serving eggs and pancakes to generations of Vermonters. Their grilled cheese is basic diner fare, made quick and cheap.
Unfortunately, it tasted like an afterthought. The cheese barely melted, the bread was limp, and the whole thing lacked any real flavor.
It is the kind of sandwich you order when nothing else sounds good, but you won’t remember it tomorrow. Burlington has better options, trust me on this one.
7. Cafe on Main — Stowe (Deliver)
Nestled right in Stowe’s tourist hub, Cafe on Main somehow dodges the tourist trap curse. Their grilled cheese arrives hot, buttery, and loaded with local aged cheddar that has that tangy bite you crave.
They grill it low and slow, so the bread gets golden without burning. The result? Cheese that melts evenly and doesn’t turn into rubber.
Pair it with their tomato soup, and you might just forget you came to Vermont for skiing, not sandwiches.
8. Mon Vert Cafe — Woodstock (Deliver)
Mon Vert is tiny, cozy, and smells like butter the second you walk in. Their grilled cheese is simple but executed flawlessly, with two-year aged cheddar that crumbles slightly before melting into creamy heaven.
They butter both sides of the bread, giving it that diner-style crunch that makes you want to order three more.
The chef told me they use a cast-iron skillet, which explains the even browning. Sometimes simplicity wins, and this sandwich proves it every single time.
9. Red Hen Baking Co. — Middlesex (Deliver)
Walking into Red Hen feels like stepping into your coolest aunt’s kitchen, if she happened to bake bread for a living.
Their grilled cheese uses house-made sourdough that crackles when you bite it, paired with sharp Vermont cheddar that stretches like taffy.
Fun fact: this place started in a garage in 1999 and now supplies half the state. The cheese gets crispy on the edges, caramelized to perfection, while staying gooey in the middle. Absolute perfection on a plate.
10. Worthy Kitchen — Woodstock (Deliver)
Worthy Kitchen takes grilled cheese seriously, like Ivy League seriously. They source their cheddar from Grafton Village, a cheese maker that has been perfecting the craft since 1892.
The sandwich comes on thick-cut farmhouse bread that tastes faintly sweet, balancing the sharpness of the aged cheddar beautifully.
Every bite delivers that satisfying cheese pull you see in commercials. It’s fancy without being fussy, and honestly, that’s the Vermont way right there.