There is a particular quality of light that falls across Port Jefferson Harbor in the late afternoon—a golden, maritime refraction that painters William Moore Davis and Leon Foster Jones spent their entire careers trying to capture on canvas in the nineteenth century. It is the kind of light that makes you slow down, that makes you notice the way shadows lengthen across the oak floors of a two-story building perched at the harbor’s edge, where the menu on the table in front of you is not so much a list of dishes as a calendar of the earth’s recent generosity. This is The Fifth Season, and it has been quietly redefining what it means to eat well on Long Island’s North Shore for over two decades.
Founded in 2004 in the wine-country hamlet of Greenport by Chef Erik Orlowski, the restaurant was born from a simple but radical premise: that the finest dining experience emerges not from importing luxury ingredients across continents, but from listening to the land directly beneath your feet. When Chef Orlowski returned to Long Island’s East End to realize his long-held dream, he opened an American bistro with a deliberately small menu—just five appetizers and five entrées—each rotating with the rhythm of what local farms and waters could actually provide at peak quality. It was farm-to-table before the phrase became a marketing platitude, a member of Slow Food USA before the movement had reached mainstream American consciousness (Slow Food International, 1986). In the spring of 2008, the restaurant made its pivotal relocation to Port Jefferson Harbor, where it has since become the number-one ranked restaurant in Port Jefferson on TripAdvisor and earned a 4.8-star rating across more than 3,200 reviews on OpenTable.
The Philosophy of the Name
The concept behind the name reveals everything about what distinguishes this establishment from the standard waterfront dining experience. Most of us celebrate four seasons. The Fifth Season is the experience that emerges when a kitchen commits fully to serving ingredients only at the absolute zenith of their natural cycle—that transcendent moment when a tomato is no longer merely ripe but incandescent with flavor, when a scallop pulled from local waters carries the cold mineral signature of the Long Island Sound itself. It is, as the restaurant’s founders describe it, “the idea of only eating the finest ingredients at the peak of their season.” The menu changes every twelve weeks, a cadence dictated not by corporate quarterly reports but by the biological calendar of Suffolk County’s agricultural landscape.
This is a philosophy I understand intimately. At The Heritage Diner, twenty-five years of sourcing from local producers has taught me that the relationship between a kitchen and its surrounding farmland is not a supply chain—it is a conversation. When you know your growers by name, when you understand the microclimates of the North Shore’s glacial moraine soil, the ingredients arrive carrying stories that a Sysco truck simply cannot deliver. The Fifth Season takes this understanding and elevates it to the level of fine art.
The Chefs Behind the Kitchen
The creative partnership that drives The Fifth Season is a collaboration between Chef Erik Orlowski and Chef John Urbinati, a duo whose combined expertise spans decades of culinary exploration across the American landscape. Orlowski, who trained extensively before returning to Long Island’s East End, brings a deep knowledge of local ingredients and an open-kitchen sensibility that invites diners into the creative process. Urbinati, alongside his wife and business partner Deborah Urbinati, contributes a seasoned understanding of hospitality, wine pairing, and the operational discipline required to maintain excellence across years, not just evenings.
When asked by Dan’s Papers about the relationship between East End wine and the local culinary culture, the chefs offered a response that reads like a manifesto: “We truly believe that what grows together, goes together. We feel that every year the bond between farmers and restaurants increases, thus allowing for fresher, local, and more sustainable products being served to our community” (Dan’s Papers, 2015). Their recommended dish to try at least once in a lifetime? Slow-roasted Berkshire pork belly—crispy skin, with meat and fat that literally dissolve on the palate. It is the kind of recommendation that reveals a kitchen operating not from trend analysis but from genuine sensory conviction.
The Dining Experience: Harbor, Hearth, and Craft Cocktails
Port Jefferson Harbor provides The Fifth Season with something no interior designer could fabricate: a living, breathing backdrop of maritime activity—ferries crossing to Bridgeport, Connecticut on the route P.T. Barnum himself championed in 1883, sailboats navigating one of the North Shore’s premier deep-water harbors, and the occasional golden sunset that transforms the Long Island Sound into something resembling hammered copper. The restaurant’s multi-floor layout within a charming converted building features solid oak floors, a beautiful banister, large harbor-facing windows, and an indoor fireplace that anchors the winter dining room in warmth. There is seasonal outdoor patio seating, an upstairs bar and lounge, and private event spaces that can accommodate everything from an intimate rehearsal dinner to a celebration of one hundred guests.
The beverage program deserves its own paragraph. House-infused artisan cocktails, made with seasonal purées and fresh-squeezed juices, rotate with the same disciplined seasonality as the food menu. The wine list is curated from American producers, with special by-the-glass selections designed to complement whatever the kitchen is featuring that quarter. Local tap beers—including selections from nearby Port Jeff Brewing Company, Blue Point, and Greenport Harbor—reinforce the restaurant’s commitment to regional sourcing. The cocktail offerings have included inspired combinations like a Bartlett pear and ginger option alongside a pomegranate and anise martini, each reflecting the kitchen’s broader philosophy that what grows in this season belongs in your glass as well as on your plate.
Community, Charity, and the Soul of Port Jefferson
What elevates The Fifth Season beyond excellent cuisine into genuine community institution is the philanthropic work of John and Deborah Urbinati. Named 2023 People of the Year by TBR News Media, the couple has built a sustained, weekly commitment to the Ronald McDonald Family Room at Stony Brook Children’s Hospital. Every Wednesday, the Urbinatis and their staff prepare and deliver fresh, hot meals to families whose children are receiving care—a commitment that has continued for nearly a decade.
“The last thing these families think about is food in such a stressful setting,” John has noted (TBR News Media, 2023). The couple recounts how a young patient who had tasted their chicken fingers in the Family Room eventually visited the restaurant herself—and when she unfortunately returned to the hospital, The Fifth Season ensured chicken fingers were specially delivered to her every week. “It’s almost a full circle moment—we support them, so they support us,” Deborah reflected. As the Ronald McDonald House Charities New York Metro has recognized, the Urbinatis’ work represents precisely the kind of local restaurant partnership that sustains families through the most difficult chapters of their lives (RMHC New York Metro, 2025).
This depth of community investment is something I recognize and respect. Operating a restaurant for a quarter century, as I have at The Heritage Diner in Mount Sinai—just a short drive east along Route 25A—teaches you that a dining establishment is not merely a business. It is a civic anchor. The same instinct that compels a restaurateur to know their farmers by name is the instinct that compels them to feed their community’s most vulnerable members. It is the unseen detail that defines the masterpiece.
What to Order: A Seasonal Guide
Because the menu rotates quarterly, offering specific dish recommendations is like trying to pin down a moving target—which is precisely the point. However, certain anchoring preparations have earned legendary status among regulars. The Snake River Farms American Kobe Sliders have developed a devoted following, with DoorDash reviewers reporting ordering them upward of fifteen times. The truffle fries appear across multiple seasons to near-universal acclaim. Grilled gulf shrimp preparations, often accompanied by napa cabbage with cucumber slaw and toasted sesame, showcase the kitchen’s ability to let pristine seafood speak without drowning it in sauce.
The prix fixe dinner option represents extraordinary value, offering a multi-course experience that allows the chefs to tell the full story of the current season. Sunday brunch has become a destination unto itself, and the restaurant’s catering division, led by Deborah Urbinati, brings the same farm-to-table precision to off-site weddings and events. Guest after guest on The Knot and other wedding platforms describes Fifth Season wedding catering as simply the best food their guests have ever experienced at a reception—a testament to the kitchen’s ability to scale its philosophy without compromising its standards.
For those who value gluten-free or plant-forward dining, The Fifth Season maintains robust organic and gluten-free offerings throughout every seasonal rotation, a thoughtful accommodation that reflects the kitchen’s broader understanding that dietary integrity and culinary excellence are not competing priorities.
A North Shore Gem in an Extraordinary Setting
Port Jefferson itself is an extraordinary stage for this restaurant. The village’s history as Suffolk County’s largest shipbuilding center—four out of ten ships built in the county were constructed here—has left behind a Historic District of ninety-eight buildings spanning Greek Revival and Italianate architecture, listed on the National Register of Historic Places in 2005 (National Register of Historic Places, 2005). The Mather House Museum, Theatre Three, the Long Island Explorium, and a year-round farmer’s market at the Village Center all contribute to a cultural density that rivals towns twice its size. The annual Dickens Festival every December transforms the streets into a Victorian pageant. For those arriving by water, the deep-draft harbor offers transient boaters easy access to the entire village within walking distance.
This convergence of culture, maritime heritage, and culinary excellence is precisely what makes the North Shore a compelling real estate story as well. My wife Paola and I, as we prepare to launch our boutique real estate venture, Maison Pawli, in 2026, consistently find that the villages with the strongest culinary and cultural identities—the Port Jeffersons, the Northports, the Cold Spring Harbors—command premiums not because of square footage alone, but because they offer the intangible asset of belonging to a living, breathing community. Restaurants like The Fifth Season don’t just fill tables; they anchor property values.
Multimedia Resources:
- Dan Barber’s TED Talk, “How I Fell in Love with a Fish,” exploring the philosophy of ecological farming and seasonal cooking that informs restaurants like The Fifth Season: https://www.ted.com/talks/dan_barber_how_i_fell_in_love_with_a_fish
- Dan Barber’s TED Talk, “A Foie Gras Parable,” on sustainable food production and the ethics of pleasure in dining: https://www.ted.com/talks/dan_barber_a_foie_gras_parable
The great Italian gastronome Carlo Petrini, who founded the Slow Food movement in 1986 as a protest against the homogenization of taste, argued that food should be “good, clean, and fair”—good in quality and flavor, clean in its impact on the earth, and fair in its treatment of the people who produce it. The Fifth Season, operating from its harbor-side perch in Port Jefferson for more than two decades, embodies all three principles with a quiet authority that requires no manifesto, no celebrity endorsement, no viral social media moment. It needs only a diner willing to sit down, to notice the light falling across the oak floors, and to taste what happens when a kitchen surrenders its ego to the calendar of the land.
Some restaurants chase trends. Others chase stars. The Fifth Season chases seasons—and in doing so, has built something far more durable than either.
Essential Information:
Address: 34 East Broadway, Port Jefferson, NY 11777
Phone: (631) 477-8500
Website: https://thefifth-season.com
Reservations: Available via OpenTable
DoorDash: Order Delivery
Instagram: @fifthseasonrestaurant
Private Events: Contact Deborah Urbinati at (631) 477-8500 ext. 4
Hours:
- Monday: Closed
- Tuesday–Thursday: 4:00 PM – 8:00 PM
- Friday–Saturday: 4:00 PM – 9:00 PM
- Sunday: 11:00 AM – 7:00 PM
Dining Style: Casual Elegant | Farm-to-Table New American
Price Range: $$
Features: Full Bar, Happy Hour, Prix Fixe Menu, Outdoor Patio, Harbor Views, Private Dining Rooms, Indoor Fireplace, Gluten-Free Options, Wheelchair Accessible, Takeout, Catering (On & Off-Premise), Wedding Services
Parking: Municipal metered parking available in the Village of Port Jefferson
Getting There: Take the Long Island Expressway to Exit 64, north on Route 112 to the harbor. Also accessible via the LIRR Port Jefferson Branch and the Bridgeport & Port Jefferson Ferry from Connecticut.
