Westchesterites have no problem traveling to a neighboring county for quality eats. From Stamford, Norwalk, and Westport to the Ridgefield-New Canaan-Wilton area, these 10 Fairfield County restaurants are well worth the phrase, “Have food, will travel.”
23 Bailey Ave, Ridgefield; 203.431.0796
Located on an alleyway road right off bustling Main Street, Bailey’s Backyard has been a town mainstay for 20 years and counting. Cozy and inviting, it feels like you’re dining in someone’s lit up backyard patio. The secret to its success, according to owner Sal Bagliavio, is that Bailey’s was farm-to-table before the term was even coined, the first of its kind in Ridgefield.
On the menu, expect an ever-changing, seasonal approach that’s not afraid to push the envelope. (Right now, it’s all about homey, winter dishes, like duck or fork-tender short ribs with root vegetables, roast chicken with lentils and bacon, and homemade pappardelle in wild boar Bolognese.) The Wednesday four-course tasting for $40 (or $65 with beverage pairings) is a steal.
Photo by Andrew Dominick
371 Shippan Ave, Stamford; 203.324.1651
Take everything you know about your grandfather’s classic red sauce joint, remix it, and you have Café Silvium. For more than 18 years, this Shippan neighborhood gem has been one of the toughest dinnertime tables to get. (Advance reservations are strongly encouraged for weeknights; it’s first come, first serve on weekends, so expect to line up in the parking lot.)
What awaits are hefty portions of pasta — most of which are homemade — freshly made burrata with thin-sliced prosciutto, fall-off-the-bone pork osso buco, and baseball-sized meatballs with whipped ricotta. Matching the generous Italian comfort food are the lofty wine pours (somewhat of a legend in their own right) that are a drop away from overflowing.
Photo courtesy of The Cottage
256 Post Rd E, Westport; 203.557.3701
Downtown Rye can get a taste of Brian Lewis’ modern Japanese cuisine with the recent opening of OKO in the former Rosemary & Vine space, but you’ll want to trek to Westport for his New American flagship, The Cottage. While The Cottage flashes Lewis’ passion for Asian flavors with do-it-yourself wagyu bao and decadent duck fried rice with yolky quail eggs, there’s also a nod to Italy with a trio of fresh pastas, seasonal small plates featuring local produce, and a burger that takes no backseat to the restaurant’s fine-dining menu.
Always save room for their hot fudge and peanut butter sundae.
967 Ethan Allen Hwy, Ridgefield; 203.438.6033
If there’s one type of food people will travel for, it’s high quality BBQ. That’s exactly what you’ll get at Hoodoo Brown, whose Texas-inspired ’cue has blown up via a cult social media following and a packed dining room most nights. (You can order the full menu at the bar to avoid the wait.) There’s no wrong answer when it comes to choosing smoked meats for a build-your-own platter, but Hoodoo’s standouts are their juicy salt-and-pepper brisket, pork belly with chicharron-like skin, and brontosaurus-sized beef ribs.
Want more? Show up on Prime Rib Thursdays for a smoked, thick-cut of steak or to their brand-new Tex Mex Tuesdays —yeah, that means BBQ tacos — on the first Tuesday of the month.
19 Bridge Sq, Westport; 203.557.8775
On any given night the dimly lit, cozy confines of Kawa Ni are packed with diners slurping spicy miso and porky, garlicky ramen bowls to warm their souls. At Bill Taibe’s Japanese-inspired izakaya, they’re also sipping spirit-forward cocktails, gulping down pints of Sapporo, and totally not refusing to shoot one of the many sake-bomb shots on the menu.
Continue soaking up the rice beer and whiskey with other Asian pub-grub pleasures like crispy fried karaage (Japanese fried chicken), hot-oil Szechuan pork dumplings, smoked bone marrow, or the always satisfying crab fried rice with salty Benton’s bacon and a runny egg.
10a First St, Norwalk; 203.354.3194
Connecticut is known for its abundance of warm, buttery lobster rolls. In a short amount of time — like as soon as it opened in 2017 — Knot Norm’s tender, meaty, butter-drenched version on griddled split rolls put them on the map. But owner Jay LeBlanc’s chef-driven spin on a New England seafood shack is so much more.
Menu items like fried whole clam bellies clams, roasted oysters, smoked BBQ “rolls,” and hot-oil jumbo chicken wings all appear simple, but at first bite you’ll know you’re eating at a special place.
Photo courtesy of Match
98 Washington St, Norwalk; 203.852.1088
Since 1999, Match has been a lively, trendy, consistently tasty, celebration-appropriate fixture in the heart of SoNo. When chef-owner Matt Storch opened the restaurant, the refined, unpretentious menu was ahead of its time. Pillow-soft ricotta gnocchi with braised oxtail, thin-and-crispy wood-fired pizzas, sesame-wasabi tuna, and Carpetbaggers, deep-fried local oysters with black-truffle cream, are all Storch specialties that remain today.
Calling it all “American” is fair, but you’ll see plenty of Italian and Vietnamese represented, too, and its evolution added more small plates, plus a buttery Florentine steak for two and a stellar cocktail program. Don’t miss the burger: Dunked in homemade cheese sauce and topped with bacon and onion jam, it has its own dedicated night (Thursday).
Photo by Stephanie Webster
151 Bedford St, Stamford; 203.801.7577
Westchester fans of Mecha Noodle Bar can rejoice: You no longer have to schlep it to Norwalk to get your slurp on! Downtown Stamford’s iteration of the popular noodle shop, which opened in September, has all the pho, ramen, and fried-chicken bao the brand is known for. The difference? A bigger bar — arrive early for a chance to snag a limited, bar-only katsu burger — and the shareable Baller Menu, featuring a punch-bowl cocktail and a dry-aged porterhouse with a big bowl of pho for two.
Speaking of the bar, Jonathan Rodriguez’s beverage program is no second fiddle to the food. His thoughtful creations range from tiki drinks to classic cocktails and others libations using Asian flavors.
34 Cannon Rd, Wilton; 203.834.9816
Housed in a renovated 1872 schoolhouse, The Schoolhouse at Cannondale is easily one of the more charming restaurants in the Tri-State, and it’s got the cuisine to match. Chef Tim LaBant’s contemporary American style showcases the bounty of Connecticut farms without overcomplicating it. Nailing down signatures is tough with a menu that changes daily, but each visually stunning, fresh dish will make date night, or whatever you’re celebrating, totally worth it.
If you’re on a budget, take advantage of Thursday’s four-course $48 special or visit for lunch on Friday or Saturday.
15 Elm St, New Canaan; 203.920.1212
“Snacks +Taps” is the moniker at this speakeasy (false front door and all) that’s an alter ego of its fine-dining sister restaurant, South End, a few blocks away. Cocktails, which change frequently, go by numbers rather than quirky names, and fun shots, beer, and wine on tap help make an ordinary night legendary.
The bar-friendly food is better than you’d expect, with nearly everything made in-house (even the ketchup!), and a menu that’s mostly gluten-free. Deep-fried cheese curds, pork belly bao, shaved rib-eye cheesesteaks, and a gourmet riff on the Double-Double should all get your consideration.
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