According to Islands.com, one Connecticut town is getting some well-deserved national attention, and it’s probably not the one you’d expect.
When people think about standout Connecticut destinations, places like Mystic, Greenwich, or New Haven usually dominate the conversation. But this time, the spotlight is on Cheshire, which was recently recognized as one of the best places to live in the state.
The national travel website points to Cheshire’s combination of small-town charm, outdoor recreation, local businesses, and great restaurants as some of the biggest reasons it’s become such a desirable place to call home. It’s also no stranger to high rankings. Cheshire was named the best place to live in New Haven County by Niche in 2025 and has also landed on Money Magazine’s list of the best places to live in America. Its public schools continue to receive high marks as well.
One of Cheshire’s biggest draws is its access to nature. The town is home to scenic orchards, beautiful greenhouses, and is known as Connecticut’s bedding plant capital. During the fall, local farms and orchards become popular destinations for apple picking, fresh cider, and seasonal treats. Outdoor lovers also have easy access to Roaring Brook Falls, Sleeping Giant State Park, and the Farmington Canal Heritage Trail.
Of course, no Connecticut town earns national praise without having some great food. Islands.com highlighted Cheshire’s pizza scene, including Fuoco Apizza and Pop’s Pizza, along with Viron Rondo Osteria for Italian cuisine. Beer lovers can also stop by Counter Weight Brewing, while Sweet Claude’s Ice Cream and Shef’s Bagels round out the town’s lineup of local favorites.
Cheshire may not get the same attention as some of Connecticut’s bigger destinations, but this latest recognition suggests it deserves a spot on your list. Whether you’re looking for a weekend road trip or thinking about putting down roots, this quiet New Haven County town is proving it has a lot more to offer than many people realize.
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