In between two of Connecticut's biggest cities, New Haven and Hartford, you'll find the small town of Cheshire, a community built around outdoorsy escapes, delicious local eats, and unique shops. Whether you're wandering through one of the town's quiet orchards, setting out on woodsy trails, or sitting down for dinner, there's plenty to love here. It's even known as the state's bedding plant capital, featuring lovely green spaces that fit in among other Connecticut gems like America's oldest public
rose garden.
There are plenty of reasons people enjoy living in this quaint New England town. In 2025, Niche ranked Cheshire the number one place to live in New Haven County and the 14th best place to live in Connecticut as a whole. In 2020, it placed 28th on Money Magazine's list of America's best places to live. Cheshire's public school system also receives top marks — it was ranked eighth in the state in 2023. So, whether you're just passing through or looking for somewhere new to settle down, you'll find a taste of the good life here — it's up to you to decide if it's being served up at a local eatery or freshly picked off an apple tree.
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Explore Shops, Orchards, And Other Things To Do In Cheshire
You don't have to tour all of the roughly 1 million square feet of greenhouse space in the bedding plant capital of Connecticut, but you can see some beautiful plants and flowers at places like Tower Farms and Cheshire Nursery. Come fall, farms in Cheshire are filled with happy customers picking fresh fruit, enjoying farm activities, and eating delicious fall treats. Drazen Hill Orchards, Old Bishop Farm, and Hickory Hill Orchard all showcase the best that autumn in New England has to offer.
If you've still got the outdoor bug, visit Roaring Brook Falls, the second-largest waterfall in the state , which is just as destination-worthy as the waterfall at this lush Connecticut state park. The Falls Trail to Roaring Brook is only 1.5 miles, but nearby Sleeping Giant State Park has 32 miles of hiking trails to explore. The Farmington Canal Heritage Trail also travels through town, giving residents a chance to explore a paved path (with only a few unfinished sections) that runs 54 miles north to the Massachusetts border.
And it wouldn't be a visit to a quaint New England town without a few souvenirs, so be sure to check out some of Cheshire's unique shops. Seems Like Yesterday is an adorable hub of vintage furniture and collectibles, and The Red Owl has jewelry and gifts to keep you looking and feeling great. But the shop that best embodies this close-knit community is ReRead Books, a used bookstore that helps provide job training for individuals with special needs.
Find The Best Places To Eat In Cheshire, Connecticut
Most foodies who visit New Haven County are there with a purpose — to get an exceptional slice (or two) from the unexpected pizza capital of the U.S. Even though Cheshire doesn't claim to compete with New Haven, it still does the region proud. Stop by for a coal-fired slice at Fuoco Apizza (which was given 8.5 stars by Barstool Sports in 2023) or Pop's Pizza down the street. Pop's has been serving slices in town since 1987.
Pizza isn't the only Italian food in town, though. Viron Rondo Osteria dishes up Italian cuisine and has a large outdoor patio that's great on summer nights. In fact, Connecticut Magazine rated Viron Rondo a top outdoor dining option in 2025 and noted its excellent wine selection. And speaking of delicious drinks, Cheshire is also home to one of the country's top breweries, according to VinePair.com. Counter Weight Brewing serves up a blend of traditional beers and trendy offerings at a sprawling facility that features fun events and some pizza of its own.
Elsewhere in Cheshire, you'll find the kind of small-town eateries you might expect. Located in a former factory that now serves part-time as an art gallery, Sweet Claude's Ice Cream is a beloved maker of delicious homemade ice cream. And don't leave town without swinging by Shef's Bagels, purveyors of old-fashioned, hand-rolled bagels.
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