There is a particular quality of light inside certain restaurants that cannot be designed by an architect or specified by an interior decorator. It arrives only after decades of accumulated warmth — the residue of ten thousand candlelit dinners, the slow amber burnishing of wooden booths by shoulders pressed against them in laughter, the way late-afternoon sun catches a vase of fresh flowers on a table that has hosted first dates, anniversaries, baby showers, and at least one New Year’s Eve wedding. Walk into Pasta Pasta on East Main Street in Port Jefferson Village, and you feel it immediately. This is not a restaurant that was “opened.” It was cultivated, like a garden — planted in 1991, tended by three successive stewards, and now, after more than three decades, in full and extraordinary bloom under the ownership of Debra Bowling, a woman who waited tables here for over twenty years before she ever held the keys.
Port Jefferson itself is the kind of North Shore village that makes you understand why people stay on Long Island even when Manhattan beckons. Originally known as “Drowned Meadow” — named by settler John Roe in 1682 — the village was one of the most prolific shipbuilding centers in Suffolk County through the 19th century. Four of every ten ships built in the county were constructed in its harbor (Historical Society of Greater Port Jefferson). Renamed by Jeffersonian Democrats in 1835, Port Jeff has evolved from a maritime outpost into one of Long Island’s most cherished waterfront destinations, its walkable downtown a living catalog of boutiques, galleries, and restaurants anchored by the Bridgeport & Port Jefferson Steamboat Company ferry that still connects Long Island to Connecticut multiple times a day. The Port Jefferson Village Historic District, listed on the National Register of Historic Places in 2005, encompasses 98 contributing structures — a rare concentration of architectural continuity on the North Shore (National Park Service, 2005). Into this rich tapestry of history, culture, and coastal beauty, Pasta Pasta has woven itself as something close to essential.
From Pizza Joint to North Shore Institution: The Origins
The story of Pasta Pasta begins in 1991, when the restaurant first opened its doors at 234 East Main Street, initially operating as a more modest establishment focused on pizza and pasta preparations in a candlelit atmosphere. It was a good restaurant, popular with locals, but it had not yet become what it would be. That transformation began in earnest when Steve Sands, a graduate of the Culinary Institute of America with over forty years of professional kitchen experience, and his business partner Jules Buitron, purchased the restaurant in the late 1990s. Sands and Buitron already owned a restaurant on the South Shore, but they had long admired the Port Jeff location and recognized its potential. Their vision was to evolve the menu far beyond its original scope — to create something that honored the Italian-American foundation while embracing a broader, more innovative New American culinary identity. Under their stewardship, Pasta Pasta became a place where you could order a filet mignon served over toasted gnocchi tossed with roasted garlic, sage, prosciutto, arugula, and a splash of marsala wine — a dish that remains one of the most popular entrées on the dinner menu to this day. As Great Restaurants of Long Island Magazine noted in their review, Sands and Buitron made the restaurant feel simultaneously sophisticated and casually exciting.
A Waitress Becomes an Owner: The Debra Bowling Chapter
The most extraordinary chapter in Pasta Pasta’s history is also its most recent. Debra Bowling joined the restaurant in 1998, hired as a waitress by Sands and Buitron just as they were beginning their expansion of the menu and ambiance. Over the next two decades, she became the face of the restaurant — hostess, manager, server, and the person who remembered your name, your usual order, and the last time you brought your mother-in-law for her birthday. When Sands and Buitron began contemplating retirement, Bowling was the first person they approached about purchasing the business. There was never really a question. As Sands would later reflect, she knew the business, the customers, and the kitchen crew — many of whom had been there since before Sands himself had arrived (TBR News Media, 2019).
Bowling officially took over ownership in January 2019, with her husband Jerry and their six children — Emma, Luke, Ryan, Blake, Mike, and a sixth — forming the operational backbone of the new era. Emma hosts. Luke runs food. Mike handles marketing. Jerry mans the phone and pitches in wherever the moment demands. The transition was seamless because it was, in the truest sense, a family succession — not of bloodlines to the previous owners, but of devotion to the place itself. Bowling still waits tables. She has said, with characteristic directness, that she never plans to stop. The response from the community was overwhelming. Regulars who had traveled from across Long Island and beyond to eat at Pasta Pasta for years welcomed the change with open arms, some moved to tears by the continuity of it all. A couple who had their first date at Pasta Pasta on New Year’s Eve returned two years later to hold their wedding reception in the same dining room (TBR News Media, 2019).
The Tuscan Villa: Atmosphere as Philosophy
Step inside Pasta Pasta and the aesthetic registers immediately — warm light wood accents, vases filled with fresh flowers, candlelit tables, antique mirrors, and framed art prints that evoke the casual elegance of a Tuscan countryside dining room. The restaurant was redecorated to reflect this villa-inspired ambiance, and the effect is neither pretentious nor theatrical. It is comfortable in the way that only genuinely loved spaces can be. Romantic booths are separated by curtains, creating intimate enclaves within the larger room — perfect for a couple’s anniversary or a quiet conversation that the neighboring table does not need to hear. The private party room accommodates up to sixty guests for showers, birthdays, retirements, holiday gatherings, and the kind of family events that become annual traditions.
This attention to atmosphere is not accidental. In the restaurant world, there is a term borrowed from the sociologist Ray Oldenburg — “the third place” — referring to spaces that are neither home nor workplace but serve as anchors of community life (Oldenburg, The Great Good Place, 1989). The Heritage Diner, where I have spent the last quarter-century behind the counter in Mount Sinai, operates on the same principle. A restaurant that survives for decades does so not merely because its food is good, but because it becomes a space people need — a place where the waitress knows your name, the bread arrives warm before you order it, and the candlelight makes even a Tuesday evening feel like an occasion. Pasta Pasta has achieved this distinction with remarkable consistency.
The Menu: Far More Than the Name Suggests
One of the most endearing misconceptions about Pasta Pasta is embedded in its very name. Newcomers arrive expecting baked ziti and stuffed shells. They will not find either. As owners Debra and Jerry Bowling have explained, the menu is best described as New American with Italian roots — a designation that encompasses an astonishing range of preparation and ambition. Executive Chef Martin and his kitchen team offer a menu that pivots effortlessly from delicate starters like wasabi-crusted calamari drizzled with General Tso’s sauce and wasabi aioli, to hearty mains like the Black Angus New York shell steak served with mashed potatoes, sautéed spinach, and crispy onions.
The duck program deserves particular mention. Pasta Pasta sources its duck from Crescent Duck Farm in Aquebogue — a fifth-generation family operation founded in 1908 that remains the last duck farm on Long Island and one of the most respected producers in the country (Crescent Duck Farm). The Duck Two Ways preparation features a seared breast alongside duck confit risotto with sautéed spinach and a red wine port reduction — a dish that honors both the French tradition of duck cookery and the Long Island provenance of its primary ingredient. The seafood pizza, topped with lobster meat, crabmeat, and calamari in a spicy plum tomato sauce with asiago and mozzarella, speaks to the same coastal abundance that makes Port Jefferson’s harbor restaurants special. The brick-oven pizzas — including a Tuscan preparation with portobello mushrooms, spinach, prosciutto, pine nuts, and smoked gouda — have become signature items that regulars order with the confidence of tradition.
The Sunday brunch features its own inventions, including a Prosciutto Eggs Benedict with fresh basil hollandaise and a breakfast burrito with house-made pico de gallo. The prix fixe menus — available at lunch and dinner — remain one of the best dining values on the North Shore, offering three courses at accessible price points that make Pasta Pasta a weeknight option as much as a special-occasion destination. Gluten-free menus are available for both lunch and dinner, and the restaurant has expanded its offerings to include no-carb and no-sugar options — a nod to evolving dietary sensibilities that Bowling implemented shortly after taking ownership.
Awards, Recognition, and the Voice of the Community
Pasta Pasta was named Best Italian Restaurant on Long Island in the 2025 Daily Voice Readers’ Choice Awards — a recognition that validated what the North Shore dining community had known for years (Daily Voice, 2025). The restaurant holds a Tripadvisor Travelers’ Choice award and is ranked among the top three restaurants in Port Jefferson on the platform, with a 4.2-star rating across 276 reviews. On OpenTable, verified diners consistently praise the restaurant as a neighborhood gem, highlighting both the quality of the pasta dishes and the warmth of the service. Google reviewers have assigned a 4.4-star rating, and Restaurant Guru reports a 4.5-star aggregate across nearly five thousand reviews. On Yelp, Pasta Pasta has accumulated 483 reviews and 456 photos — a visual testament to a dining community that wants to share what they have found.
The restaurant is a regular participant in Long Island Restaurant Week, where it has offered its prix fixe menu alongside other Port Jefferson establishments including The Fifth Season, Ruvo, and Black Pearl Seafood Chophouse. Pasta Pasta also participates in the annual A Taste of Port Jefferson, the Greater Port Jefferson Chamber of Commerce’s signature food event, where it shares billing with the village’s finest culinary establishments. During the COVID-19 pandemic, Bowling pivoted to takeout operations and was deeply moved by the community’s response — regulars showed up not just to order food but to hand cash directly to kitchen workers whose hours had been cut, asking simply if the restaurant was going to be okay (TBR News Media, 2021).
Practical Information: Getting to Your Table
Address: 234 East Main Street, Port Jefferson, NY 11777
Phone: (631) 331-5335
Website: pastapastaportjeff.com
Online Ordering: Available through Toast at order.toasttab.com/online/pasta-pasta-port-jefferson
Reservations: Available via OpenTable
Instagram: @pastapasta_portjeff
Hours:
- Monday–Thursday: 11:30 AM – 8:30 PM
- Friday–Saturday: 11:30 AM – 9:30 PM
- Sunday: 11:00 AM – 8:30 PM (Brunch 11:00 AM – 2:00 PM)
Prix Fixe Dinner: Monday–Friday 4:30–6:00 PM, Saturday until 5:30 PM, Sunday 3:00–5:00 PM (not available on holidays)
Monday Night Dinner for Two special available weekly
Private Events: Party room accommodates up to 60 guests. Catering platters and hot food available for home events.
Parking: Public paid parking lot available in Port Jefferson Village. Weekday rates are $1.00 per hour; Friday–Sunday rates are $3.00 per hour from noon to 8:00 PM. Arrive early on weekends, as the village fills quickly during peak dining hours.
Getting There: Take the Long Island Expressway to Exit 64, travel north on Route 112 to Port Jefferson Village. The restaurant is located in the heart of downtown, steps from the harbor. The Port Jefferson LIRR station is a short ride share away, and the Bridgeport & Port Jefferson Ferry terminal is within walking distance for visitors arriving from Connecticut.
The Bread, the Light, the Table That Remembers You
There is something about Pasta Pasta’s house-baked bread that deserves its own sentence in any honest account of this restaurant. It arrives warm, flaky, and fragrant before your appetizer, and it has inspired the kind of loyalty that transcends the merely culinary. Regulars have described it as the reason they drive past a dozen other Italian restaurants to reach East Main Street. It is not a bread that tries to impress. It is a bread that tries to nourish — and in that distinction lies the entire philosophy of this place.
In my twenty-five years of running The Heritage Diner just up Route 25A in Mount Sinai, I have watched restaurants open and close with the regularity of tides. The ones that endure share a common quality: they are owned by people who would rather serve a meal than manage a brand. Debra Bowling is that kind of owner. She bought a restaurant she had already given two decades of her life to, and her first instinct was not to change the name or redesign the menu — it was to keep serving. That instinct, that refusal to distance herself from the dining room floor even after she held the deed, is why Pasta Pasta has outlasted trends, survived a pandemic, and earned the kind of community devotion that no marketing budget can purchase. It is, in the most fundamental sense, a family restaurant — not because it has a children’s menu (though it does), but because the family that runs it treats every guest as if they belong at the table.
Port Jefferson is blessed with extraordinary dining options — from the waterfront sophistication of Black Pearl at Danford’s to the seasonal farm-to-table inventions at The Fifth Season. But Pasta Pasta occupies a space that is uniquely its own: the warm, candlelit center of a village that still believes a great meal is an act of hospitality, not a transaction. If you have not been, go. If it has been too long, go back. The bread will be warm. The flowers will be fresh. And someone behind the curtained booth will be celebrating something worth remembering.
Peter from The Heritage Diner | heritagediner.com/blog Photography and multimedia sourced from verified public platforms.
