Overlooking the scenic Port Jefferson Harbor, this elevated dining spot brings together refined American cuisine, a stylish bar scene, and one of the best waterfront views on Long Island. It's an ideal setting for date nights, weekend brunches, or after-work cocktails with a view.

Inside, the ambiance is modern yet cozy, with large windows that frame the marina just steps away. The décor is clean and elegant, and the dining room flows into a well-stocked bar that’s just as much a destination as the food itself.

The menu is seasonally driven, crafted with fresh ingredients and creative flair. Whether you’re savoring a perfectly seared scallop dish, a tender filet mignon, or a vegetarian risotto bursting with local vegetables, each plate reflects attention to detail and bold, balanced flavors. Brunch and lunch options are just as impressive, offering lighter fare with upscale touches.

Food & Drink Review

Start the evening with shareable small plates—try the crispy Cauliflower Fritters with tangy herb aioli or the rich Truffle Mac & Cheese Bites. Their Fig & Prosciutto Flatbread blends sweet and savory, and the fresh Beet & Goat Cheese Salad provides a vibrant contrast.

For mains, the Pan-Seared Salmon comes with a delicate citrus glaze and seasonal vegetables, while the Short Rib Ravioli in a red wine demi‑glace is a hearty, comforting standout. The Herb‑Crusted Chicken breast is juicy and well-balanced with garlic‑thyme jus and roasted fingerlings. Their seasonal seafood features—like clams, mussels, or scallops—are often served with house-made broth and fresh herbs.

The cocktail program is thoughtful and playful. Try the Ginger Pear Mule or the Blackberry Bourbon Smash. Wine lovers will appreciate the curated list featuring crisp New York whites, chilled rosés, and bold Pacific Northwest pinots. Local craft beers on tap ensure there’s something for everyone.

Lively Nightlife Vibe
Evenings at The Fifth Season are relaxed yet vibrant. Soft lighting, warm woods, and exposed brick create a cozy backdrop for weekend dinners. On Friday and Saturday nights, the bar area fills with friends catching up, and occasional acoustic music or jazz sets enhance the atmosphere without stealing the spotlight. It’s the kind of place where you're just as likely to linger over cocktails as you are to settle in for a full meal.

The best time to visit is just before dusk, when the light fades over the harbor and the restaurant takes on a golden, coastal glow. With exceptional food, a vibrant bar, and stunning views, this is Port Jefferson dining at its finest—elevated, approachable, and unforgettable.