Cherries Roadside

Cherries Roadside on Route 209 in Stone Ridge is one of those places that proves you should never drive past a little white roadside shack with a swirl cone cutout on the sign. This community institution has been serving locals and road-trippers since the 1950s, and it’s the kind of spot that somehow manages to feel both deeply nostalgic and completely fresh at the same time.

The current chapter of Cherries started when Lawrence O’Toole and Jolene Delisle — a couple who relocated from Manhattan’s Upper West Side to the Hudson Valley in 2020 looking for a quieter life — fell in love with the place during the pandemic. When they heard the previous owner was selling, they jumped on it, did an intensive renovation including replacing nearly the entire kitchen, and reopened with a clear vision: classic roadside-stand food, but made with genuinely good ingredients. Everything is GMO-free and locally sourced whenever possible. Grass-fed beef burgers, hickory-smoked all-beef hot dogs, hormone-free chicken, and even a flame-broiled quinoa veggie burger for the plant-based crowd. And the fries are cooked in sunflower or coconut oil, because of course they are.

But let’s be honest — the ice cream is the star. Cherries makes its own small-batch ice cream, and the flavors range from beloved classics like cookies and cream and cherry chocolate chunk to rotating seasonal surprises like oat milk banana cookie. There are also gourmet fruit popsicles, sundaes, and shakes. Food critics have called it maybe the best deli in all of upstate New York, and it landed on the list of the 25 Best Restaurants in the Catskills. Not bad for a roadside shack.

It’s open seven days a week, 11am to 9pm, all year round — which in the land of seasonal everything is frankly heroic. There’s also a curated little general store on site. It’s casual, it’s family-friendly, it’s affordable, and it’s exactly the kind of place that makes living in or visiting the Hudson Valley feel like a very good decision.