When you’re already in love, Valentine’s Day presents a wonderful opportunity to stop and smell the roses. With romance inherently in the air, Cupid eschews his arrows for chocolate-covered strawberries and champagne.
When you’re single, it’s a different story. Valentine’s Day can hit hard. It might be the best thing to happen to you. It might be the worst. Ultimately, it might not matter at all.
The real question is: Why overthink it and miss a celebration? Let’s share the love!
Every V-Day event we could find in and around Ulster County awaits you below. On this crimson-hued love train to Bacchanal City, we’re here to connect you with the celebration that matches your unique style and relationship status.
Valentine’s day is for everyone, because everyone deserves to be loved. Now pucker up. Cupid’s watching.
A feast for all senses
Enjoying top muscial talent while dining on fine food and drink is an experience that defines cultured luxury. What better way to spoil the one you love?
Buzzy bar/restaurant Darlings in Tilson will host live music by Kyle Miller and Photon Beam on Tue. Feb. 14 at 7pm. The night will be taken up another notch with romantic food and drinks specials, including some surprises.
Woodstock’s own Simi Stone will present a “Supper Club” experience at Colony Tue. Feb. 14, with doors opening at 6pm, followed by a three-course prix fixe dinner. Stone is known locally as one of the area’s most accomplished musicians, and known the world over for her many releases and collaborations. Her style is smooth and sophisticated, full of soul, energy and grace.
Also on Valentine’s Day proper, the Avalon Lounge in Catskill will host a “Bed of Roses” event featuring DJ Tall Matt spinning “love-based records” from 7pm-10pm. Admission of $40 per person includes a prix fixe menu, special appetizer, entree, dessert from Chimes bakery and a champagne (or non-alcoholic) cocktail. Reservations required.
Will you be vine?
How did wine become the most romantic alcohol? Some say it was a cultural construction, others point to the careful craftsmanship that goes into each bottle as a representation of the similar process of relationship-building. Whatever the origins, our area’s wineries are celebrating in due course.
Robibo Winery in New Paltz will host lavish, five-course wine-and-chocolate tasting flights every weekend in February from 11am-6pm. The confections are supplied by Wallkill’s Hudson Valley Chocolates. Reservations can be locked in at $35 per person.
Love is in the grapes at Benmarl Winery in Marlboro, who are hosting their annual Valentine’s Day wine and cheese pairing through Feb. 20. Sample four wines and a board of Hudson Valley cheeses, local jams and housemade chocolates. Admission is $35 and reservations are available on the hour.
Another Marlboro winery, Quartz Rock Vineyard, will offer their finest wines alongside gourmet, chewy chocolate chip cookies from Desiré, and live music from local singer/songwriter Callie Mackenzie. A wood-burning stove, gorgeous views and friendly staff make Quartz Rock a perfect destination for super-casual intimacy.
What’s my age again?
Call it anti-Valentine’s Day if you must. The pop punk and emo tradition is to wear one’s bleeding heart on one’s sleeve. Romance can be as much about emotional suffering as it is triumph, and the catharsis of loud, melodic music cannot be denied in this regard.
Whether you’re a jaded, heartbroken “solo artist” or the member of a duo nostalgic for those warm summer emo nights, there are several options for a holiday seemingly precision-designed to create and support the punk/emo genre.
Anti-Valentine’s Day at Hudson Brewing Company invites you to sing along to all your favorite pop punk and emo classics with HBC and This Is Emo on Sat. Feb. 11. There will be drink specials and a s’more station. (You can really learn a lot about someone by watching them eat really messy food.) Your inner teenager will appreciate the lack of cover charge.
Up in Albany at Empire Live, another “Anti-Valentine’s Day Emo Party” kicks off Sat. Feb. 11 at 8pm with Sad Dads, Terralite, E.R.I.E., Nikki Brown & The Well Diggers. Tickets start at $17.45, and the show draws like-minded, black-clad minds from all over the region.
Quite a checkered-Vans Valentine’s Day weekend is shaping up at Hudson Valley Resort & Spa at Kerhonkson, with the love of ska taking center stage at the “Hoppy Valentine’s Masquerade Ball”. Check out this skankified lineup: Pietasters, Hub City Stompers, Samurai Pizza Cats, Stop The Presses, Skappository, Typhoid Rosie, Gratefully Yours… and the list goes on. BYOB and enjoy a laser light show, craft vendors and a heated indoor pool as you dance the night away in your checkered Chucks. The festivities unfold on Fri. Feb. 10 and Sat. Feb. 11.
My funny Valentine
A sense of humor is always prized in a partner, and the couple that laughs together lasts together. As long as they’re not laughing at each other.
On Sat. Feb. 11, a Valentine’s Comedy Gala will take over Mahoney’s Irish Pub & Steakhouse in Poughkeepsie. Presented by Laugh It Up Comedy Club, the side-splitting affair features Ryan Denisco from WPDH and WRRV, Patty Rosborough as seen on Comedy Central and HBO Max, Molly Kornfeld from New York Comedy Festival. The whole shebang is hosted by Jeffrey Paul from The Irishman. Doors open 6:30, buffet spreads at 7pm, show starts at 8pm. $75 per person includes tax & gratuity, along with a glass of champagne and chocolate strawberries to end the evening.
Also happening that Saturday at Cafe Maroon & Club in Poughkeepsie is a comedy show hosted by Her & I Production with BET & Def Comedy Jams comic Hamburger, flanked by fellow stand-up sensation Ms. Jones and DJ Don Don. There are two shows (6pm & 9pm) and an afterparty ‘till 4am. The best-dressed Valentines win prizes, and there’s also a 50/50 raffle to keep things interesting.
Crimes of passion
Who knew Valentine’s Day was a magnet for murder mystery events? In a culture obsessed with true crime series and podcasts, it makes sense. We crave intensity and drama, and the murder mystery allows partners to experience all of this while coupling as a detective duo, growing closer as they work with other guests to get to the bottom of things. Solo investigators get the perfect platform to mingle while stimulating their sleuth neurons.
An innovative Valentine’s Day-themed murder mystery dinner titled A Recipe to Die For will be presented by Theatre on the Road at Kingston’s Best Western on Feb. 8 at 7pm. These affairs are often period pieces with lavish costumes, but this time around we get a refreshing, modern take with inspiration from cooking competition shows like Chopped.
The plot involves four celebrity bakers competing for the position of pastry chef at your restaurant. Each must prepare an original dessert recipe, and both actors and attendees will act as judges. Of course, murder is also on the menu, and you’ll need to gather clues and interrogate characters to out the killer. Tickets are $75 and available on Eventbrite.
Revel 32° in Poughkeepsie will host its own Valentine’s Murder Mystery on Sat. Feb. 11 at 7pm. This one’s for speakeasy fans, titled Death of a Gangster, 1920’s Mafia Marriage. Expect over-the-top performances, a gourmet charcuterie table, decadent desserts, and specialty cocktails, featuring boozy coffees. Tickets start at $59 and include everything but the booze.
If you prefer a more traditional detective experience, Blue Arrow Farm in Pine Island is doing a 4-course meal with a cash bar centered around a murder mystery investigated by none other than Sherlock Holmes. Audience participation and even prizes await those savvy enough to navigate the clues.
Treats for sweeties
Just in time for Valentine’s Day, Emily’s Cookie Co. will throw its grand opening celebration this Sat. Feb. 11 at 1pm in Port Ewen. Its owners will be cutting the ribbon on their new baked-goods business, and a dizzying array of sugar-bombs including royal icing sugar cookies, cakes, cupcakes, cake popsicles, along with Oreos and strawberries covered in chocolate.
Of course, you can’t go wrong with our area’s incredible selection of gourmet chocolatiers, who will be tempering chocolate at breakneck speeds over this critical confectioner’s holiday. Among the most sumptuous are: Fruition Chocolate (Shokan), Krause’s Chocolate (Saugerties, Rhinebeck and New Paltz), Lucky Chocolates (Saugerties), Oliver Kita Chocolate Studio and Cacao Lab (Kingston).
If you’re a more ambitious foodie looking to truly earn your Valentine’s Day dessert, check out the V-day-themed cooking class for couples on Wed. Feb. 8 at Ulster County BOCES at 5pm. Titled “Cooking With Love: Valentine’s Day Dinner for Two”, the class features Culinary Institute of America-trained chefs walking couples through making a three-course meal, followed by a tasting of their dishes. Bring $100 per couple, an apron and a hair covering.
Unconditional love
Armadillo in Kingston will host a “Crazy Fur You Valentine Dinner” benefitting the UCSPCA on Mon. Feb. 13 at 6pm. This four-course dinner features their famous chips and salsa, empanadas with crème fraiche, a crisp chopped salad, entrée choices of veggie or chicken burrito, or chipotle pasta with vegetables or chicken. Save room for Armadillo’s signature churros with Nutella. Tickets are available for $60 on the UCSPCA website.
A decadent dance
For some lovers, the fancier the better when it comes to celebrating our nationally recognized day of love.
The Grandview in Poughkeepsie has traditionally hosted one of the area’s toppest-shelf bashes. This year on Tue. Feb. 14, they’re at it again with a mouthwatering menu featuring – sorry if you’re hungry while reading this – shrimp cocktail, grilled ribeye, stuffed free range chicken, pan-seared salmon, grilled portobello mushroom napoleon with sinful sweets like dessert martinis, truffles, creme brulee, “let’s make whoopie” pies, fresh beignets, a crepe station, and warm churros. Oh, and four hours of literal top-shelf open bar, including champagne and wine service. And a box of one dozen long-stemmed red roses. Dress to the nines, pony up $162.95 + 22% service charge (plus tax), and you’ll be dancing among Valentine’s elite.
Eye of the beholder
Pearl Moon in Woodstock will host a late-night burlesque extravaganza titled “Cupid’s Cabaret” on Sat. Feb. 11 at 9:30, featuring performances by Trust La Noir, Lady Fingers, Purple, Chevie Supernova and Moelani. The sexiest pick on our Valentine’s list also boasts raffles and prizes for further excitement, with an after party to follow into the wee hours.
The Heartbreak Hotel installation at Poughkeepsie’s Reason & Ruckus is an over-the-top production featuring the works of local and international artists. There will be a burlesque showcase, live music, live art, “anything but cash” casino, comedy showcase, artist games and speed daging. Over 50 artists have contributed pieces. A professional chef and a whole team of mixologists will create palate-pleasing sensations throughout the night. Catch the party Fri. Feb. 10 or Sat. Feb. 11 at 6pm. Each night has different programming, so be sure to check their website for details.
If you really want to turn up the heat, let’s just say Club Blue Moon in New Paltz (established 2000) has survived as the county’s only strip club for a reason. Their Valentine’s party is Wed. Feb. 15. ‘Nuff said.
Heart-to-table dining
It would be impossible to list all of the area restaurants offering special Valentine’s day menus and experiences, so let’s do some speed dating with a few in-demand candidates.
Kingston: Sonder wine bar and restaurant is intimate, sophisticated, fairly new to the area and well worth the experience. Ship to Shore is the go-to upscale surf-and-turf experience for diners who appreciate class and confidence. Le Canard Enchaine is the decadent choice for French cuisine, the food of love. Italians may beg to differ, in which case Stella’s Restaurant’s refined homestyle plates never fail, and Savona’s Trattoria pleases with clean Italian-American offerings and numerous specials. Who’s eating the last breadstick?
New Paltz: Garvan’s frequently tops the list of most romantic restaurants in town, with an old-style vibe, excellent food and attentive service. A Tavola Trattoria is known for its “stylishly rustic” ambience and Italian delicacies made from local, seasonal ingredients. If Latin-American flavors are more your thing, check out Rubirosa Cucina & Bar for picture- and palate-perfect plates.
Woodstock: Red Onion stood the test of time as a multifaceted upscale restaurant with elite service and accessible, unpretentious culinary decadence. Cucina has superb atmosphere and Italian dishes that deliver on homestyle flavor through the filter of fine dining. Silvia is a super-classy contemporary American joint where complex flavor profiles sing in harmony. Their open kitchen is a stage for the spectacle of culinary wizardry.
Saugerties: Diamond Mills Hotel is always a Valentine’s Day hotspot with majestic waterfall views, soaring ceilings and refined atmosphere. Annarella Ristorante bursts and blushes with romantic vibes, gorgeous ambience, attentive staff and expertly crafted Italian dishes. One might say Salt & Fire is the new kid on the block, but somehow the restaurant’s already fully grown, fast gaining a reputation as the foodie’s choice in Saugerties.
Didn’t see your favorite V-day destination? Got a hot tip on a romantic hotspot in and around Ulster County? Leave us a comment or suggestion at the bottom of this page.
Join the family! 
