I try not to fall too hard for tourist towns. Even the good ones can leave me feeling a little used or hoodwinked, with that slightly sour “and all I got was this lousy t-shirt” aftertaste. I try to resist the obvious adjectives, especially “amazing” and “cute.”
But, dammit, Chester is cute. And amazing. I love it, unabashedly and despite myself. You see, Chester is the sweet, small town I thought only existed in the movies. Black and white ones. Where else, other than on a Hollywood backlot or the Hallmark Channel, could one block of Main Street magically meet all of one’s needs on a lazy weekend afternoon? And do it so… cutely?
With architectural holdovers from its early days as a mill town and shipbuilding center, Chester is an awfully handsome little hamlet—that frustratingly photogenic crush you try to ignore because everybody likes them. But you like them, too. You can’t help it.
Its quaint and shockingly dense commercial center, less than a quarter mile long and just a single mile from one of the prettiest bends in the Connecticut River, is bookended by two lovely restaurants. To the west, inside a converted savings bank built in 1902, is Grano Arso. A regular on ‘best of’ lists, it doesn’t need me to sing its praises. But I’ve never had a disappointing meal there, and more than once I’ve driven the 40 minutes from New Haven just for a well-balanced cocktail and the rigatoni bolognese. At the eastern end is Otto, a warm and homey pizza joint with a straightforward menu and a prominent wood-burning oven. Their sauce is distinctive, their cheese from Liuzzi (enough said). The exposed kitchen is confident and makes dining at the bar feel interactive. A subtle Italian lager from High Nine Brewing in nearby Deep River harmonized perfectly with the fresh rosemary that dressed our still-bubbling pepperoni pizza.
After eating your fill at either end of Main, head to the local watering hole, Pattaconk 1850. If only every bar could deliver the effortless comfort and charm of this place. Named for the brook that winds adorably through town, the white tin ceiling makes great use of the daylight that pours in off the street, bathing the well-worn bar top with enough illumination to read a novel by. They’ve got pleasant and satisfying food on the menu, with a section devoted to Nashville chicken and a few vegan/vegetarian nods like buffalo cauliflower and an Impossible burger. Their tap list is extensive and featured a dry cider, a tipple too rare if you ask me. I could’ve spent the rest of the day there, but a nagging desire for dessert pulled us back to the street.
That’s because the business next door happens to be my favorite ice cream shop in the state. Opened in 2020, Honeycone Craft Ice Cream is overseen by a talented mother-daughter team. This family doesn’t miss, as far as I can tell, with selections like mango mascarpone, red velvet and cardamom rose. If you’re feeling a little lactose intolerant, they’ve got dairy-free options as well.
Our next and last stop was the brewery across the street. Little House Brewing manages to pack a production facility and small bar into its tiny, eponymous storefront. Though present, IPAs don’t dominate their tap list, and half the menu is 5% ABV or less. The variety of styles available when I was there included a black Kolsch, fruited sour, Belgian tripel and a cream ale named for Otto, where we began our day. Their branding is pitch perfect, and their decidedly not-lousy t-shirts make for an excellent day-trip souvenir. You can also grab a 32 oz. crowler of something and bring a little Chester home with you.
Along with more dining options than we have room for here, there’s no shortage of boutiques and galleries in downtown Chester. They might be just as good as the restaurants and bars, but I’m not much of a shopper and my walls are full. I did however swing through a minimalist handmade leather goods store called Blackkat and seriously considered a new belt.
If the diminishing number of parking options is any indication, the word is out on Chester, Connecticut. I’d be upset with all the tourists fawning over it, if I wasn’t, well, one of them.
Written and photographed by Chris Renton.>
