Valentine’s Day is on a Saturday this year, upping the chances you can spend a day basking in love without worrying about work. Yet, figuring out plans that meet the moment may be the largest and most stressful task on your to-do list.
Indeed, Valentine’s Day has gotten a reputation for being a Hallmark holiday; an excuse to extend the holiday spending season past the December budget-breaking point (you can even get matching family Valentine’s Day jammies!). Yet, love is at the heart of the holiday, and that’s worth celebrating, especially now. Around the North Fork, wineries, restaurants and inns are making plans simpler with unique events, menus and packages you and yours will love. From cupcakes and bubbly to a masquerade ball, here’s what to do on the North Fork for Valentine’s Day in 2026.
Pindar Vineyards, 37645 NY-25, Peconic, 631-734-6200
With a sprawling vineyard, an also spacious tasting room and a calendar packed with live music, Pindar is one of the North Fork’s most happening vineyards all year long. This year, its V-Day lineup is dreamy for people with a sweet tooth and/or non-traditional work schedule. Instead of limiting the North Fork Chocolate pairing menu to the weekend, Pindar will offer it daily from February 9 through 15. That means you can toast to your love with local chocolate in hand on a Monday if you fancy. Tickets cost $30 per person (Wine club members can get in on the fun for $25). Reservations recommended.
Get gooey, warm and toast-worthy at Suhru this Valentine’s Day. (Photo credit: Alicia Ekeler)
Suhru & Lieb Vineyards, 13050 Oregon Road, Cutchogue, 631-734-1100
This cozy Cutchogue vineyard is adding fondue for two to its tasting room menu, and turning Valentine’s Day into an all-weekend affair. From 12 p.m. to 5 p.m. on Feb. 13-15, couples can indulge in the smooth, creamy tastes of Raclette Fondue. The $28 per person ticket ($56/couple) also includes two vinos of your choice. Heads up: The reservations are for two people only. If you’re making this an event for a group, add the guests’ names to your reservation notes so the tasting room can plan to keep your crew together.
Sparkling Pointe Vineyards & Winery, 39750 County Road 48, Southold, 631-765-0200
How sweet it is and has been on Valentine’s Day at Sparkling Pointe. The bubbly-centric vineyard has made its sparkling wine-and-cupcake pairing a tradition, and it returns for a 15th year in 2026. Guests can nibble on three mini cupcakes that go big on flavor, along with a flight of three sparkling vinos. Additional wines by the glass and à la carte food pairings are also on the table if you please. It’s all happening in Sparkling Pointe’s pristine and poppy tasting room, where colorful art juxtaposes perfectly against whitewashed walls for an elegant yet fun date-day setting. Tickets cost$30 per person plus tax, and the menu is on tap from Feb. 14-16.
North Fork Table & Inn, 57225 Main Road, Southold, 631-765-0177
Found in a countryside home, this locavore-forward restaurant with soft lighting will emerge from its short winter’s nap in time for Valentine’s Day. A three-course prix fix menu ($125) includes an option to upgrade to wine pairings ($92). Surf-and-turf appetizers and mains include tuna tartar, smoked chicken, and sea bass. Or, marry surf with turf by ordering an entrée with petit filet mignon, butter-poached lobster and potato pureé. A warm chocolate cake for dessert will offset whatever Mother Nature is doing.
Chronicle Wines, 2885 Peconic Lane, Peconic, 631-488-0046
We love when boutique winemakers Robin Epperson McCarthy and Alie Shaper of Chronicle Wines pair up with the maven of marvelous sweet treats, Ali Katz. For Valentine’s, hit up Chronicle’s lovely, cozy little tasting den on Feb. 13 and 14 for a decadent wine pairing to fall for: Ali Katz Kitchen’s rich chocolate ganache cake and heart-shaped Linzer tarts paired with your choice of two glasses of wines from the Chronicle family. $55 per couple ($45 for club members) nabs you two glasses of wine and both desserts all V-Day weekend long.
Bistro 72, 1830 W Main St., Riverhead, 631-369-3325
A three-course prix fixe menu is on tap for Valentine’s Day at Bistro72, the unpretentious yet chic farm-to-table restaurant set within Hotel Indigo. Start with something warm (French onion soup or calamari) or light (salad) before digging into hearty mains like a rack of lamb or filet mignon. Dessert offerings include a rich mini velvet cake or tiramisu. If that special someone is eyeing a Valentine’s weekend of romance, spend Friday, February 13, at Hotel Indigo. A Valentine’s package includes an overnight stay for two and a Valentine’s breakfast in bed with an on-the-house mimosa or bloody Mary. Then, digest with spa services — a couple’s massage is on the menu.
The East Wind, 5720 NY-25A, Wading River, 631-846-2335
The usual dinner-for-two is fun and all, but The East Wind has another option for couples and friend groups who find that whole thing tried and getting truly trite. The East Wind’s masquerade ball lets you don your dancing shoes and formal attire for an elegant (and mysterious) night of romance. A few clues it’ll be a blast, though: There will be a DJ, buffet dinner and four-hour open bar from 7 p.m. to 11 p.m. Tickets are $135 plus tax per person, or get the gang together. It’s $110 per person for parties of eight or more. Extend the night and skip the Uber by booking an overnight stay. A $499 package deal scores you tickets and a room.
Desmond’s, 5720 NY-25A, Wading River, 631-846-2335
If you’re looking for something lower key, this snug Italian-focused restaurant within East Wind is serving that up in dinner-date fashion, steps away from the masquerade ball. Stare deeply into one another’s unmasked faces over a bottle of red (white or rosé instead), plus dishes like lobster pasta, wild mushroom ravioli, or Tuscan chicken with Fontina cheese wrapped in prosciutto.
Long Island Aquarium, 431 E Main St., Riverhead, 631-208-9200
Chocolate and wine are a Valentine’s Day power couple. Mix in an ambiance that scores 14/10 for uniqueness (a backdrop of marine life, like sharks), and you’ve got yourself a date that’ll go over swimmingly. Long Island Aquarium’s annual Chocovino event will include a five-course meal. Each course will incorporate chocolate and come with a vino from Raphael wine. The event takes place on February 14 from 7 to 10 p.m and costs $175+ per person, or you can turn the night into a weekend getaway with a stay at the Hyatt ($529+ and includes two tickets to the event).
Ram’s Head Inn, 108 S. Ram Island Drive, Shelter Island, 631-749-0811
Perhaps no local establishment is getting into the Valentine’s Day spirit like this Shelter Island, which dates back to 1929. The sweeping waterfront views are romantic 24/7/365, but Ram’s Head Inn is pulling all the (heart)strings to make V-Day 2026 one to remember. Programming includes a Murder Mystery Party ($95 per person, February 13), a three-course dinner and cabaret (February 14, $195 per person), and brunch with your dog (February 15, and no dog? ARF is bringing 10 to meet, greet and maybe apply for adopting). Couples can also take advantage of one- or two-night packages that include perks like champagne and chocolate-covered strawberries.
The Suffolk, 118 E Main St, Riverhead, 631-727-4343
Suffolk’s February 15 “Unforgettable Valentine” Night is proof positive that love really is patient. Listen to Nat King Cole’s timeless library of soulful hits like “Unforgettable” and “Smile” as performed by Jerome Foster Lewis and talented instrumentalists. It’s a night sure to live up to its name. Tickets are required and start at $35.
Vine Street Café. 41 S. Ferry Road, Shelter Island, 631-749-3210
Lobster Pot Pie, bouillabaisse and baked Alaska are among the soul and bone-warming dishes Vine Street Café will serve on Valentine’s Day. The cottage-style digs and amiable services will feel like a loving embrace in their own right.
Lumber + Salt, 5570 Sound Ave., Jamesport, 215-704-6588
Express your love through cheese! Head to Lumber + Salt’s cozy indoor café for a Raclette party on Feb. 14. With hot, cheesy fun and homemade Bavarian pretzels courtesy of Greenport’s Alpina, groove to vinyl-centric sounds curated by local fave DJ Henry Eau. The ooey-gooey shenanigans start at noon and last ’til 4 p.m.
