13 Valentine’s Day Events for Fun and Romance in the Hudson Valley

Love should be honored and celebrated year-round—and twofold on Valentine’s Day. Whether you’re spending the holiday with your long-term love, a new sweetie, or just using the day as an excuse to appreciate your closest friends (and indulge in a little chocolate), we’ve rounded up some Hudson Valley happenings sure to help you celebrate the spirit of Eros in all its forms.

City Winery Hudson Valley | Montgomery NY | @citywineryhv | INSIDE+OUT spotlight

Chocolate & Wine – what better pairing to toast to your love? Enjoy an exclusive selection of Håkan chocolates paired with City Winery wines, just in time for Valentine’s Day. Featuring two selections, guests choose a red or white wine flight, accompanied by three carefully curated chocolates, picked and paired by Håkan and City WInery Winemaker, Travis Van Caster. This tasting experience makes for the perfect date night or stellar Gallentine’s celebration.

White Wine Flight
2023 Gewurztraminer with Cardamom Cookie
2022 Pét-Nat Rosé with Strawberry & Champagne
2022 Riesling “Vin de Glaciere” Ice Wine with Passion Fruit & Grapefruit

Red Wine Flight
2020 Syrah “Au Naturel” with Cloudberry & Coffee Bonbon
2022 Bourbon Barrel Aged Merlot with Lingonberry & Whiskey Bonbon
2017 “The Encore” Port-Style Wine with Tahitian Vanilla & Pear Cognac Bonbon

Mohonk Mountain House | New Paltz NY | @mohonkmountainhouse

Romance Week | Feb 11th – 16th
Revel in romance all week with a distinguished getaway filled with fun, relaxing and intimate activities, including cocktail tastings, spa treatments, dinners, ice skating, games and crafts like Bingo and origami lessons, or just cozying by the fireplace with your dearest.

Cindy Cashdollar at VFW Post 1386 | Kingston | @shotofsilvercindycashdollar | Read Our Exclusive Interview with Cindy

The Honky Hearts Ball | Feb 14th at 7:15 pm
The Local | Feb 24th at 8pm
After a successful run of Honky Tonk Nights at the VFW hall, five-time Grammy Award winner Cindy Cashdollar leads her band, The New Original Locals, for a night of country-western music on Valentine’s night. Admission is only $10; $20 for the show and a couples dance lesson, and fine dress is encouraged. Cashdollar will also perform later in the month at The Local (Feb 24th at 8 pm) with supergroup Toombs Dixon as the venue kicks off their Saugerties Sessions music series.

Benmarl Winery | Marlboro NY | @benmarlwinery

Annual Valentine’s Day Wine & Cheese Pairing | Feb 2nd – 25th
Benmarl is offering hourlong wine, cheese and chocolate pairing experiences throughout February. Each reservation includes four wines and a curated cheese board with locally sourced cheeses, jams and housemade chocolates for groups of up to four. The events are $35 and can be reserved on their website.

Hudson House Distillery | West Park NY | @hudsonhousedistillery

Valentine’s Day Heart Platter Cookie Decorating Class | Feb 10th at 2 pm – 4 pm
A fun experience for couples who like to share a kitchen or for your Galentine tribe: Learn how to create a Valentine’s-themed cookie platter while enjoying a drink from The Hudson House’s top-notch bar. All cookies, icing, and supplies are provided as a teacher from Elemental Cookies guides you through this beginner-level class. RSVP here.

FurEver Friends Hudson Valley | Wappingers Falls NY | @fureverfriendsfamily

FurEver Friends Valentine’s Day Celebration! | Feb 10th at 1 pm – 4 pm
There truly is no other love than that from a pet, so let’s celebrate our furry friends, too, this Valentine’s. This pup-friendly celebration includes treats for all, pet portraits, vendors, raffles and, of course, puppies.

Dassai Blue Sake Brewery | Hyde Park NY | @dassai_blue

Valentine’s 3-Course Dinner & Sake Pairing | Feb 10th at 5 pm – 8 pm
The Hudson Valley’s new and highly acclaimed sake brewery is hosting a Valentine’s dinner experience that includes a tour of the $85 million facility, a sake tasting, and a three-course dinner presented by the Culinary Institute of America.

Lux Hair Studio | Saugerties NY | @luxhairstudiosaugerties

Valentine’s Day Prep Event | Feb 3rd at 2 pm

Celebrate self-love and be your own Valentine, whether you’ve got a hot date or not. Treat yourself at this popular salon and beauty studio with a scalp and hair treatment, hair styling, mini facial, light snacks—plus a little bubbly and more at $55 per person. Make a reservation by calling 845-246-2221.

Robibero Winery | New Paltz NY | @robiberowinery

Wine with your Valentine | Feb 10th + 11th + 14th + 17th + 18th
Reserve a table for this highly popular wine and chocolate pairing event. Each 90-minute session includes five wines paired with five local chocolates at $35 per person. After the sampling, guests can enjoy the afternoon at the winery or sit beside the fire pit. Reserve online.

Chapel of Sacred Mirrors (CoSM) | Wappingers Falls NY | @chapelofsacredmirrors

Valentine’s Weekend at CoSM with Alex Grey & Allyson Grey | Feb 10th: Dinner + Feb 11th: Brunch
This weekend at spiritual center CoSM features a weekend of exploring the concept of love and partnership with artists Alex and Allyson Grey. During “An Evening of Love: Valentine’s Dinner & Dialogues” (Feb 10th), couples enjoy dinner, discussions, and connection with others, centered around the concepts of falling in love and sustaining relationships. On Feb 11th, during “Love & Partnership: Valentine’s Brunch & Talk on Sacred Couples,” guests enjoy brunch before workshops exploring how couples communicate, bond and can lead a spiritual and creative life together. For details about admission, accommodations and more, contact [email protected].

Edgewood Mansion at Hutton Brickyards | Kingston NY | @huttonbrickyards

“Marriage Can Be Murder” – A Valentine’s Day-themed Murder Mystery | Feb 3rd at 6 pm – 9 pm
A classic murder mystery dinner by acclaimed theater troupe Murder Cafe adds lively fun to your Valentine’s plans with a romance-inspired whodunnit. For $100 per person, guests enjoy an immersive show with prizes and a three-course pre-fixe dinner that includes a complimentary glass of wine or beer. Reserve online.

Quartz Rock Vineyard | Marlboro NY | @quartzrockvineyard

No Pressure Valentine’s Day | Feb 10th + 11th
Speed Dating | Feb 10th + Mar 2nd
If you’re seeking a laid-back, romantic way to enjoy Valentine’s weekend without the extra pink hearts and fluff, Quartz Rock’s No Pressure Valentine’s Day events offer just that. For $25, you’ll enjoy wine tasting, cupcakes from Desiré and seating in their cozy tasting room with live music by Adam Fitch (Feb 10th) or Dan Stevens (Feb 11th). Looking for love, a new relationship, or just an extremely fun night? Sign up for one of their singles’ Speed Dating events: “Man seeking woman, Woman seeking man” on Feb 10th and “LGBTQ+ on Mar 2nd. Tickets are available online.

Cooper’s Daughter Spirits at Olde York Farm | Claverack NY | @coopersdaughterspirits

Valentine’s Happy Hour at Cooper’s Daughter Spirits | Feb 16th at 4 pm – 8 pm
The Cooper’s Daughter Cocktail Barn & Garden will be open for an extended all-night happy hour in their heated cocktail barn. Specials on Valentine’s-themed cocktails and pub food by a local food truck offer an easy way to celebrate the holiday with a date or friends.

Happy Valentines Day!