15 hours of eating and drinking in downtown Oyster Bay

7 AM : Southdown Coffee

49 Audrey Avenue

This growing coffee empire is well represented on the North Shore (and beyond) and when the Oyster Bay location opened its doors, coffee aficionados cheered.

Owner and award-winning expert Mark Boccard knows his beans, and carefully roasts single origin, ethically sourced coffees from around the world. Sample whole and ground beans from Guatemala, Mexico, Brazil, India and Colombia, or prepare to linger over an expertly made Americano, macchiato or, my favorite, a perfect cortado. Their matcha, hot or iced, is a favorite.

9 AM : Taby’s Burger House

28 Audrey Avenue

It’s time to have a proper breakfast.

And the more things change in Oyster Bay, the more Taby’s stays true to itself and its customers.

Built on the ethos of small town charm, consistency and tried-and-true favorites, Taby’s is as ingrained in Oyster Bay as Teddy Roosevelt himself. The diner specials at Tabby’s reign supreme and breakfast is thankfully served all day. (In fact, it is so good that we may have been here twice in one day, both times opting for breakfast foods).

The omelets are enormous and spot on, no matter what you opt to fill them with. Home fries and bacon are perfectly crispy, and you cannot go wrong with a fluffy stack of their pancakes. To order like a local, ask for eggs and toast with a side of waffle fries.

If you find yourself here later in the day, their ¼ pound burgers, tuna melts, grilled cheese and shoestring French fries are unrivaled. Still, don’t hesitate to check out the unsung heroes, such as the prime rib or stuffed flounder dinners. Taby’s is small town, family-owned at its best. 

Bonanza is an Italian ice institution in Oyster Bay, going on 125 years. In summer months the line snaking all the way down Audrey is filled with hungry patrons anxiously awaiting their turn at the counter. Nothing hits better than a Bonanza ice, or their first-rate and super-tender chicken tenders, the most epic chili dog or an order of perfectly crispy fries or onion rings.

They have orange soda and root beer, and believe me this place serves up magic.

Live music will be on the back patio in springtime, and you’re assured of rubbing elbows with local politicians, Oyster Bay high school kids and Mexican and other Spanish-speaking expats looking for a taste of home. 

5 PM : Teddy’s Bully Bar

46 Audrey Avenue

Let’s stop for a beer. But if you’ve been pacing yourself with the eating, better bar food cannot be found in Oyster Bay than at Teddy’s. This style-y gastropub with its cool mahogany bar and exposed brick walls is always a good idea, as are the specialty cocktails, extensive beer and wine menu and live music nightly.

Choose between fish and chips, a platter of freshly shucked oysters, a prime rib French dip, the lamb shepherds pie or pressed paninis. Check out the many local beers on offer from Oyster Bay Brew Company (next door!), as well as ones from Brooklyn and beyond.

7 PM : It’s dinner time and you have options

2 Spring

2 Spring Street

In the category of restaurants that elevate and transcend, ladies and gentlemen, I present 2 Spring. If I weren’t already local to Oyster Bay, I would consider moving to the neighborhood specifically for this restaurant. Jesse Schenker, one of New York Magazine’s “Best New Chefs” and winner of Iron Chef, is chef and proprietor. And goodness gracious can this man cook.

Pull up a bar stool and sip Champagne while enjoying oysters or caviar with a side of divine French fries. Or, cozy up with your SO at a table upstairs or in the atrium whilst swooning over bucatini with little necks and guanciale or hen of the woods mushrooms roasted with hazelnuts.

Better yet, start at the bar and make your way to a table. Food, and ambiance, this good deserves your full attention. Time your visit with truffle season and you may call a realtor.

This place is an elegant and sophisticated win-win and should not be missed. 

Autentico

124 South Street

Back in 2016, Francesco Pecoraro started a movement in Oyster Bay that is still being fully appreciated today. As one of the first and most thoughtful fine dining restaurants to open in Oyster Bay, Chef Pecoraro set the metronome in motion.

His extensive background in the varied cuisines of many Italian destinations is evident in the menu at Autentico. This is a decidedly Italian farm to table two blocks from the Long Island Sound in Oyster Bay. His care with presentation and execution is unparalleled and his ever changing menu merits exploration. The piadina, a delicately fabulous, rarely seen in the US, Adriatic flatbread cooked in a griddle begs ordering, especially when served as done here with stracciatella and prosciutto di Parma.

The spaghetti alla chitarra with vongole and peperoncino is possibly better than in Amalfi. 

And prego, the Bolognese, do not leave without having the Bolognese.

Stellina Ristorante

76 South Street

Stellina Hospitality is taking Oyster Bay by storm, and the hungry masses are better fed for it.

Tom Milana and his family stand behind each and every establishment (more to come below, hold tight) and the jewel in their crown is Stellina Ristorante, white table cloth establishment with Chef Fabrizio Faccini at the helm.

Chef Faccini is a certified Master Chef, a world renowned and a recognized delegate of the Association of Italian Chefs of New York, a frequent guest on the Food Network and a contributor to NYCWFF and City Harvest. This is seasonally inspired, authentic Italian cooking that spans the entire geography of the country and will, to be quite sure, impress and make you start planning your return even before you put your fork down.

Start with some spuntini like the fried artichokes with lemony aioli for dipping and perhaps the thyme and rosemary smoke burrata with fennel. The pizzas are divine and elegant and with wagyu bresaola, fior di latte mozzarella, or freshly shaved black truffles they are anything but your average pies. The pastas are stellar, as the name of the establishment would suggest.

The stuffed agnolotti with braised veal and truffles was perfect cold weather comfort food on a recent blustery day. You also cannot go wrong with the cacio e pepe or the perfectly seasoned and balanced bucatini with San Marzano, guanciale and Calabrian chili.

Wild Honey

1 East Main Street

Looking for a sweet little spot for dinner with beautiful windows overlooking the center of town? Wild Honey is it. Lots of flickering candle light and creative takes on new American classics make this place special and popular with locals. Mussels cooked in an iron skillet could not be more simple or more delicious.

Blackened catfish with Jambalaya sauce, a classic bouillabaisse, and the filet mignon are all consistent favorites with thoughtful touches . We loved the apple cinnamon cake with caramelized apple jam, house-made ice cream and fresh whipped cream. WIld Honey is great on a weeknight or a date night; it is the quintessential local corner restaurant we all wish existed in our own hometowns. 

8:30 PM : Sabrina’s Candy & Creamery

98 South Street

Sure, there has been a food parade in Oyster Bay since morning and you’ve been on it, but there’s always room for ice cream. Sabrina’s has great scoops, and candy by the pound. All the ice cream is from Max and Mina’s in Queens and you’ll be hard pressed to make a decision on flavors.

I’d suggest getting a large and trying several.

9 PM : The Wine Line

30 Audrey Avenue

Located just next door to the Stellina Bakery and Cafe is this cozy little wine bar and restaurant, also run by the Milana family and under the culinary direction of Chef Faccini. Grab a bar stool or cozy up on one of the lounge couches and choose from over 50 wines by the glass. This is a full menu of interesting, far reaching, expansive and diverse wines from all around the globe.

There are also unique craft cocktails (try their takes on a traditional spritz or a mojito!) and a great menu of elevated smaller plates like flatbreads, salads, cheese and charcuterie, mezze platters and handheld sandwiches. If you’re looking for a nightcap, check out The Wine Line.