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The Most Romantic Valentine’s Day Events in the Hudson Valley


Whether you’re lucky in love or single and proud, we have the perfect February 14 to-do for you.

Ah, Valentine’s Day. It’s that “love it” or “hate it” holiday that takes over stores and shops every February without fail. In the Hudson Valley, local businesses and restaurants go all out for February 14 with pre-fixe dinner specials and dreamy getaways for visiting and staycationing couples alike. Not in a relationship? Never fear! Galentine’s Day and family-centric celebrations abound throughout the Hudson River region as well.

Take a scroll through the romantic (or not) happenings in the Hudson Valley, then get planning your most unforgettable Valentine’s Day yet.

For couples:

Wine & Dine

French Kiss: Early Valentine

Marriott Pavilion, The Culinary Institute of America, Hyde Park
February 8, $28+

Now this is how to do Valentine’s Day in the Hudson Valley! A concert by soloists Christopher Brellochs and Elizabeth Gerbi kicks off the evening. For showgoers who want dinner beforehand, the CIA hosts an early meal at its Caterina de’ Medici restaurant for a limited number of guests.

Wine & Spoon Valentine’s Affair

Gardiner Liquid Mercantile, Gardiner
February 13, free with registration

On the eve of Valentine’s Day, Gardiner Liquid Mercantile opens its doors for a chocolate and wine pairing like no other. Sample Vegan Wines and bite into strawberry cheesecake and chocolate and peanut butter bites by Rebecca Carucci of Powered by Plants Consulting.

Romantic Valentine’s Day Dinner

The Blue Hen, Saratoga Springs
February 14, $95/person

For the food lover in your life, reserve a table for two at The Blue Hen’s four-course dining event. The occasion begins with starters like seared scallops with roasted chicory, then features entrees like rack of lamb with cashew gremolata and a beef Wellington for two with hen of the woods mushrooms. For dessert, you can’t go wrong with the chocolate bombe cake or the whimsical cheesecake pops.

Valentine’s Day Dinner

Goosefeather, Tarrytown
February 14, $100/person

Chef Dale Talde delivers with three courses of romantic dining on Valentine’s Day. Couples can mix and match between to-die-for bites like hen of the woods mushroom salad with a six-minute egg and truffles, lobster with black bean brown butter and potato, and chewy noodles with lamb and sesame chili. Dessert is an equally showstopping affair, with three different options that hit every sort of craving.

P.S. For anyone who wants to go the extra mile, Goosefeather offers engraved bottles of Moet Brut or Rosé for an additional $200.

Valentine’s Day Dinner

Terrapin, Rhinebeck
February 14, $79/person

In honor of the most romantic day of the year, Terrapin invites couples to celebrate with a three-course prix fixe dinner menu that includes a choice of tapas, an entrée, and dessert. Fall in love with specials like Nantucket Bay scallop ceviche and butter-poached lobster tails with ginger beurre blanc. Looking for something a bit more casual? Just drop into the Red Bistro, located next to the Dining Room, instead.


Valentine’s Day Dinner Dance

Anthony’s Pier 9, New Windsor
February 14, $155/couple

Want to dance the night away with your love? Book your spot at the annual Anthony’s Pier 9 celebration. With four hours of top-shelf open bar, a box of one dozen long-stemmed roses for each couple, and a full three-course meal, the New Windsor venue has it all. Did we mention there’s a champagne wall, too?

Valentine’s Day Dinner Dance

The Poughkeepsie Grand Hotel, Poughkeepsie
February 14, $155/couple

Want to add a little swing to your celebration? Book a spot at The Poughkeepsie Grand Hotel’s oh-so-romantic dinner and dance. Beginning at 7 p.m., diners can “cheers” at the top-shelf open bar and dine on decadent eats like NY strip steak with black truffle butter and pan-seared striped bass with Champagne beurre blanc. After savoring a chocolate sampler platter for dessert, couples can head home with a complimentary bouquet of one dozen long-stemmed roses or stay the night at The Grand. Room specials run $230/couple and include breakfast in the morning.

Annual Valentine’s Winter Ball

Villa Borghese, Wappingers Falls
February 15, $83

For dancing, dining, and drinks all night long, pick up tickets to Villa Borghese’s annual winter ball before they sell out. The romantic occasion features an inhouse catered dinner along with a five-hour top-shelf open bar and music by Jimmy Dee. All couples can go home with a complimentary photo by Micci Bebonis Photography to remember the night forever.

Valentine’s Day Dinner

Watergrasshill Bed & Breakfast, New Paltz
February 15, $172.80/couple

For a night of romance in New Paltz, look no further than Watergrasshill Bed & Breakfast. The inn hosts a special five-course chef’s table experience in which couples can watch the guest chef add finishing touches to each dish right before their eyes. Dinner is BYOB, so anyone who wants a glass of vino to go with their meal can bring their favorite bottle from home.



Escape to Emerson Resort

Emerson Resort and Spa, Mount Tremper

Add Hudson Valley romance to your Valentine’s Day plans with one of Emerson Resort’s unforgettable packages. For a spa escape, try out the couples’ soak and massage treatment, which includes a 30-minute Himalayan salt soak and a 60-minute relaxation massage along with an artisanal cheese platter, Champagne, and chocolate. If you’re looking for an all-in-one experience, the Romance or Proposal Packages are not to be missed. Emerson covers every base with flower bouquets, private dinners, and even on-site proposal coordination for guest who plan to pop the question.

Valentine’s Day at The Thayer Hotel

The Thayer Hotel, West Point
Valentine’s Day weekend

Treat your loved one to a romantic weekend at West Point’s historic Thayer Hotel. To welcome guests, the hotel offers a special overnight package which includes accommodations, dinner at MacArthur’s Riverview Restaurant, and a bottle of champagne and chocolate-covered strawberries in the room. Want to make a full experience of it? Follow along with our day trip guide to West Point while you’re there.

For anyone:


Kids Baking Valentine’s Day Sugar Cookies

Sprout Creek Farm, Poughkeepsie
February 8, $25

Kids will love this sugar-filled Valentine’s Day celebration on the farm. Designed just for children ages 8 to 12, the cookie workshop teaches attendees how to make sugar cookies from scratch and decorate them for the holiday. All kids take home cookies, a craft, and a recipe card at the end of the day. The following day, Sprout Creek hosts a Valentine’s brunch for couples and families alike.

Galentine’s Day

Gal-entine’s Day Sip & Paint

Popp’s Trophies | Laser Engraving, Walden
February 7, $30

Sip a glass of wine with the girls at this pre-Valentine’s Day paint and sip. Every participant can choose one of two paintings to recreate during the class. The $30 cost includes canvas, supplies, and light refreshments, while wine is BYOB.

Valentine’s Day Stacked “Love” Workshop

Hudson Valley Vintage, Red Hook
February 7, $45

Valentine’s Day may only take place once a year, but Hudson Valley Vintage makes love a year-round thing with this hands-on workshop. For $45, attendees can decorate and paint their own 18” “LOVE” sign to display at home throughout the year.

Annual Valentine’s Weekend Wine & Local Cheese Pairing

Benmarl Winery, Marlboro
February 8-9, 14-16; $25/person

Calling all wine lovers! This year, look no further than Benmarl for the February 14 fest of your dreams. On the weekends before and after Valentine’s Day, the Marlboro winery invites the public to its seated wine tastings. Tickets, which run $25 per person, include a sampling of five wines with New York State cheeses and house-made chocolates. Trust us, there’s no better way to spend the weekend.

Sweet & Sinful Cupcake & Wine Pairing

Robibero Winery, New Paltz
February 8-9, 15-16, $21

Robibero’s Valentine’s Day celebration has Galentine’s Day written all over it. After all, what better way to ring in the holiday with your besties than with the New Paltz winery’s signature pours alongside cupcakes by The Cake Artist? The tasting is seated, and tickets include a tasting of three additional wines (bringing the drink total up to six) at the tasting bar as well.

Pre-Valentine’s Day Trivia

Growler & Gill, Nanuet
February 9, $6

Round up your single friends, your coupled friends, your work friends, your neighbors, your…well, you get the picture, for a heated evening of trivia at Growler & Gill. The Nanuet micropub tests everyone’s romantic knowledge for the chance to win prizes from Godiva, Sonoma Grille, and the Elmwood Theater, to name only a few.

Vinyl Meltdown: Valentine’s Day Edition

Colony, Woodstock
February 14, $5

Want to move and groove this Valentine’s Day? Hit the dance floor at Colony for a DJ party with Leon Michaels, Brian Parillo, Jeff Harrington, and more. Tunes range from R&B to reggae, and there will be a full light show and mirror ball by Woodstock Music Shop to set the space aglow.

Related: These Local Valentine’s Day Gift Ideas Are Affordable AF

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