August 4, 2015 by Jessica Opatich


Port Jefferson began as a ship building hub and before that, legend has it that it was a way station for pirates heading east. Now, the quaint coastal village has long been abandoned by booty buriers, and its quaint streets are the perfect setting for a little romance.

Restaurants and bars abound, and all are within walking distance of the harbor. Seaside dinning and mood-lighting is the perfect way to make a connection with that special someone. Dan’s Papers can steer you toward the perfect spots to enjoy the pleasant seaside village.

If you want to keep it casual and hang with the locals, stop at Billie’s 1890 Saloon (304 Main St, 631-331-1890). Its large green sign, awning and shutters are impossible to miss. Have fun and mingle without committing to a three-course, sit-down dinner.

Along with Billie’s another great spot to get a burger is Gourmet Burger Bistro (5 Mill Creek Road, 631-403-4033). It’s more restaurant than pub. We recommend the Triple Smoke Burger or the Inside Out Burger.

If you’re not looking for burgers, try C’est Cheese (216 Main St, 631-403-4944) an artisanal cheese tavern that serves boutique wines, craft beers, and gourmet salads. C’est Cheese has live music every Friday and Saturday from 7-10 p.m., trivia night on Tuesdays at 7:30 with cash prizes and Thursday paint nights. So bring a date and show off your smarts or your sensitive side while nibbling on some Fromage d’Affinois. Did we also mention they had an impressive selection of craft beer? Right now they have beer from Greenport, Framboise, Chimay, peak organic, Allagash, a sour from Atlantic Beer Company, Crooked Ladder and Ommegang. We also hear they have the craft beer of all craft beers—Heady Topper. It gets busy in there though so be sure to call ahead and make a reservation!

Another great spot to pick up a pint or a growler is Port Jeff Brewing Company (22 Mill Creek Road, 877-475-2739). The mall-batch craft brewery features a seven-barrel system capable of producing 217 gallons per brew. Take your date for a tour on Saturdays beginning at 4 p.m. and visit the tasting room, which is open every day from noon-8 p.m., to try a sip or two from Port Jeff Brewing’s 12 available taps.

Mere steps away from the brewery is Port Jefferson Ice Cream Cafe (30 Chandler Square, 631-509-5845). The colorful cafe has a wide selection of ice cream and yogurt flavors. But be patient, because there is guaranteed to be a line outside of kids and adults alike.

Not up for burgers, beer, or ice cream? That’s extremely strange, but we won’t judge. How about olive oil? Thats right. Over at The Crushed Olive (25 Chandler Square, 631-509-4500) you can sample some of the very best oils and vinegars. Take a square of break and dip right into a small plate of basil organic olive oil, 18 year aged balsamic vinegar or Arbequina extra virgin olive oil.

If you’re not sure what to do next, we know someone who can tell you: Christine, the psychic at the Village Astrologer (107 West Broadway, 631-327-2857). Want to know if your date is the one? Psychic Christine might just see it in your cards. Or, if that’s a little too much for a first date, how about asking her where you’ll end up having dinner?

There are a few major spots that are musts if you want to impress on the first date—Danford’s, The Fifth Season, La Parilla and Pasta Pasta. WAVE Seafood Kitchen at Danford’s Hotel & Marina (25 East Broadway, 631-928-5200) offers a spectacular view of the Long Island Sound and the seafood is some of the freshest and most expertly prepared on the island. The Fifth Season (34 East Broadway, 631-477-8500) prides itself on its impressive seasonal menu, and it’s not an empty boast. Located just across from Danford’s, the restaurant is a locavore’s dream.

Pasta Pasta (234 East Main Street, 631-331-5335) is another local favorite. The restaurant even has a Monday night dinner for two special and gluten free dinner and lunch menus. La Parilla (9 Traders Cove, 631-509-4848) is a Spanish bistro that serves up classic Spanish dishes like homemade empanadas and paella. Everyone knows they also have the best sangria in town.

Dating in the digital age can be tricky. We overheard a Port Jeff local saying that his strict rule is to start with a coffee date. In that case, we suggest Tiger Lily Café or Toast Coffeehouse. Tiger Lily (156 East Main Street, 631-476-7080) is a totally unique spot. It’s an alternative vegetarian eatery. So, if your date likes eating greens and listening to Bikini Kill, take her (or him) here and you’re guaranteed a second date. They also have live music on “Acoustic Sundays” on the outdoor deck. Toast Coffeehouse (242 East Main Street, 631-331-6860) is a breakfast and lunch eatery and like Tiger Lily it offers an artistic vibe. Toast offers tapas, fondue, cheese plates, eclectic wines, and desserts on Friday and Saturday nights.

We’d be remiss not to mention some newcomers. Brewology (201 Main Street, 631-509-1700) is new to Port Jeff, but locals are quickly getting a taste for the science of craft beer. Along with a long list of small-batch craft beers, Brewology also serves signature cocktails and wine. If you have the first date jitters, Brewology might be your best bet for unwinding and trying something new. Not quite yet a newcomer is Muse Paintbar (134 Main Street, 631-938-7800). Art and drinking have often gone hand and hand. Muse Paintbar has taken that trope and created an experience that’s different from just a regular night at the bar. The lease for the space in Harbor Square Mall was finalized earlier this year and Muse is slated to open later this summer. So, don’t worry. If you don’t have a date yet, you have some time to find one!

We're social — follow us!

Sharing is caring — Share this with your friends