Grumpy Jack’s: Port Jefferson’s hidden gem behind the hospital

Tucked just off the main drag of Port Jefferson, Grumpy Jack’s has quietly become one of those “if you know, you know” spots locals lean on for wings, burgers, and big-game nights. It’s not on the harbor, it’s not trying to be fancy, and maybe that’s exactly why it works as well as it does.

Location and setting

Grumpy Jack’s is located at 28 Oakland Ave, Port Jefferson, NY 11777, on the side street across from Mather Hospital, a couple of blocks up from the village core.

The owners describe it as a “rustic local hangout” and a “hidden gem”, with:

• Sports on TV throughout the bar and dining areas
• Daily happy hours
• A year‑round outdoor patio that gives it a little extra breathing room compared to tighter harbor spots

Ownership, origins, and history

Corporate and ownership structure

Grumpy Jack’s operates under Grumpy Jack’s Inc., a New York domestic business corporation formed on April 5, 2007, registered in Suffolk County.

Public corporate filings list John Deery as the Chief Executive Officer (CEO) and the named contact for the corporation, making him the primary identified owner/operator on record.

Opening and evolution

The restaurant itself dates its Port Jefferson location to 2007, the same year as the corporate filing, and bills itself as a family restaurant and bar that has grown up with its regulars.

Grumpy Jack’s branding leans into:

• Family‑run feel: “Come see Jack, family, and long-time staff…”
• Emphasis on regulars and repeat customers, with multiple review platforms mentioning it as a tradition for holidays and gatherings.

Menu highlights

• Buffalo wings – arguably the signature; “Grumpy Jack’s Buffalo Chicken Wings” feature prominently on the menu and across reviews.
• ½‑pound burgers – fully customizable, with toppings like jalapeños, sautéed onions, etc.
• English‑style Fish & Chips – one of the branded menu call‑outs.
• Shepherd’s Pie (spelled variously Sheppard’s/Shepherd) – a recurring favorite noted in reviews.
• Steaks – including 16 oz. options noted on the official description.
• Starters: Calamari (multiple styles), Grumpy Sampler, steamed clams, mussels (red or white sauce), jumbo shrimp cocktail, chicken fingers, nachos, mozzarella sticks, Cajun popcorn shrimp, baked clams, fried pierogies, clams on the half shell, popcorn chicken.
• Burgers & sandwiches: ½‑lb burgers with add‑on toppings; steak sandwiches, turkey burgers, subs and handhelds noted across menu sites and reviews.
• Comfort mains: Stuffed flounder, French onion soup, chicken dinners, corned beef sandwiches, Caesar salads, seafood bisque, etc., showing a wider reach than “just wings and burgers.”

Sunday brunch program

Grumpy Jack’s runs a Sunday “Grumpy Brunch” starting at 11:30 am, including a complimentary 8 oz. mimosa or Bloody Mary with brunch.

The brunch menu features:

• Eggs Benedict (classic and avocado versions)
• Grumpy’s Egg Sandwich
• Steak and eggs
• Multiple omelets (Frisco, Philly, Grumpy, Mediterranean, etc.)

This brunch offering helps the bar & grill lean a bit more “family restaurant” during the day, while still giving the bar crowd what they want later.

Past menu versus present

Older menu captures and reviews show a very consistent core over time:

• Wings, burgers, steak sandwiches, French onion soup, pretzels, clams, and stuffed flounder appear in both older and newer reviews.
• The “Grumpy Sampler,” Bavarian pretzel, shepherd’s pie, and bar‑snack‑meets‑comfort‑food identity have remained intact, suggesting evolution by addition, not reinvention.

In other words, it’s one of those places where regulars can order “the usual” year after year without fear it disappeared in a menu makeover.

Atmosphere, reputation, and reviews

Across platforms (Tripadvisor, Restaurantji, Restaurant Guru, Google summaries) the ratings cluster in the 4.1–4.4 range out of 5, with hundreds of reviews and multiple “Travelers’ Choice”‑type recognitions.

Common themes in reviews:

• Friendly staff and service: multiple customers describe the team as attentive, engaging, and quick.
• Neighborhood bar energy: TVs, sports on, regulars at the bar, and a casual, comfortable dining room.
• Consistent food: phrases like “fresh, hot, and tasty,” and people noting they come back for holidays and special events (St. Patrick’s Day, New Year’s Eve, Mother’s Day, birthdays).
• Cozy touches: references to a fireplace and a cozy atmosphere, especially in colder months.

There are, as with any long‑running place, some mixed reviews around noise level, bar crowd, or occasional service hiccups, but nothing that stands out as a persistent pattern of serious issues across platforms.

Notable milestones and community role

• 2007: Grumpy Jack’s Inc. formed; restaurant established at 28 Oakland Ave, Port Jefferson.
• Growth as a “hidden gem”: The restaurant self‑identifies as one of Port Jeff’s “hidden gems,” and independent review counts (800+ reviews on maps and aggregators) suggest it has become a local fixture rather than a transient concept.
• Brunch & events: The addition and promotion of Sunday brunch and regular holiday/event programming (St. Patrick’s, New Year’s, etc.) helped embed Grumpy Jack’s into local calendars.

There are no widely reported, singular “headline” milestones (like celebrity chef takeovers or national TV features) surfaced in typical sources; it’s more of a steady, slow‑build local institution than a media‑driven brand.

Online presence, media, and videos

Grumpy Jack’s maintains an active online footprint:

• Official website

Quick reference: key facts

Business, ownership, and corporate info:

• Grumpy Jack’s Inc. – CorporationWiki profile (CEO listed as John Deery)
• Dun & Bradstreet business profile

Menus and reviews:

• TripAdvisor (menu, reviews)
• Restaurantji
• Restaurant Guru
• MenuPix