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Top 10 Uniquely Dutchess Valentine’s Events

Date Published: January 30, 2023

Love is in the air here in the Hudson Valley, as Valentine’s Day is right around the corner. For you born romantics out there, this is your day to shine. For the rest of us, however, here is a list of can’t-miss, uniquely Dutchess Valentine’s Day experiences that are guaranteed to sweep that special someone off his or her feet.  

Of course, dinner for two is always a safe bet, and there are plenty of Dutchess County restaurants offering special menus and dinner events for Valentine’s Day and the weekend before it. They include Shadows on the Hudson and Mill House Brewing, both in Poughkeepsie; The Villa Borghese in Wappingers Falls; Cranberry's at Tilley Hall in Hyde Park; and Charlotte's in Millbrook. 

Whatever your plans, have fun, and let Cupid’s arrows fly! 

Curry Estate
Curry Estate, Hopewell Junction

Valentine’s Day Romance Package 

Feb. 10, 11, 12 and 14 at Curry Estate, Hopewell Junction 

If you’re looking to be spoiled this Valentine’s Day, then Curry Estate has you covered. Spend a night with your significant other in the luxurious inn and receive a $200 credit to spend on a delicious dinner in the four-star restaurant. When you check in, you will find 12 long-stem roses, La Marca Prosecco, chocolate-covered strawberries and other assorted homemade treats waiting in your room. When you wake up the following morning, treat yourself to a tasty Continental breakfast. You deserve a night alone full of romance and relaxation. Click here, and let Curry Estate whisk you away. 

Jukebox Junkies Valentine’s Day Dance 

Saturday, Feb. 11, 7 p.m. at The Stissing Center, Pine Plains 

Bring that special someone to The Stissing Center and dance late into the night with the Jukebox Junkies. The Poughkeepsie-based trio plays a wide variety of familiar favorites, from the 1960s to the present. Proceeds from the event will benefit The Stissing Theatre Guild's production of “Mamma Mia!” To purchase tickets, click here. The Stissing Center is one of 12 destinations on the Dutchess Tourism Inspiration Finder Arts and Culture Trail, which will earn you discounts and perks at some of the best cultural institutions, exhibition spaces and performance venues in Dutchess. Click here for details. 

Related: Include Dutchess in Your 2023 Goals 

Valentine’s Comedy Gala 

Saturday, Feb. 11, 7 p.m. at Mahoney’s Irish Pub, Poughkeepsie 

Mahoney’s Irish Pub and Steakhouse presents a Valentine’s Comedy Gala featuring Ryan Denisco of WPDH and WRRV radio stations; Patty Rosborough whose comedic stylings have been seen on Comedy Central and HBO Max; and Molly Kornfeld, who was a hit at the New York Comedy Festival. Jeffrey Paul will host the event; he has graced the stages at New York City’s most famous comedy clubs and has several big-screen credits to his name, including “The Irishman” and “The Saint of the Impossible.” A buffet dinner starts things off, and a glass of champagne and chocolate-covered strawberries bring the evening of hilarity to a close. To reserve tickets, click here.

Donuts and Flowers and Beer...Oh My! 

Saturday and Sunday, Feb. 11-12 at Lasting Joy Brewery, Tivoli 

Head to the Lasting Joy Brewery tap room for a weekend of Valentine's fun. Beautiful bouquets from Petal Creek Farm of Milan will be available for purchase as you enjoy decadent donuts from Mighty Donuts and delicious pizza from Forno Rosso. Lasting Joy will have its new beer on tap; "Mint Condition" is a mint chocolate stout. As a bonus, Samosa Shack will be on hand on Friday providing plant-based, Indian-inspired eats. 

Related: Winter Road Trip to These Quaint Towns 

Beekman Arms Delamater Inn
Beekman Arms and Delamater Inn, Rhinebeck

“A Recipe to Die For” 

Feb. 11 and 18, 7 p.m. at The Beekman Arms, Rhinebeck 

Book your reservation at America’s oldest continuously operated inn and get ready for a fun night as the Tavern at the Beekman Arms and Delamater Inn serves up Valentine’s dinner with a side order of murder. Enjoy a delicious three-course dinner followed by a dessert competition featuring four celebrity bakers. The Hudson Valley's own Murder Cafe presents a murder mystery that will have everyone wondering “whodunit?” and “why?” To purchase tickets, click here. The Beekman Arms is one of several establishments participating this winter in the “Stay in Dutchess” program, which offers perks and deals at hotels and inns throughout the County. Click here and learn how you can stay longer – for less. 

Souper Chef Weekend and Valentine Wine Tasting

Saturday and Sunday, Feb 11 and 12 at Millbrook Vineyards and Winery, Millbrook 

Warm up every winter weekend in the Millbrook Winery’s Taproom or Bubble Lounge with a glass of wine and a hot, brimming bowl of soup or chowder made by one of Dutchess County’s finest chefs. This particular weekend, the Millbrook Winery will be dishing out Golden Nugget Squash Soup from Terrapin in Rhinebeck and Hearty Beef Chili from Fireside BBQ and Grill in Salt Point. Yum! Millbrook Winery is also hosting a special Valentine's wine tasting this weekend. Enjoy a tasty selection of local cheeses and chocolates that have been expertly paired with Millbrook Wines. Each participant receives a gift from Hudson Valley Chocolate and a souvenir Millbrook Wine glass. Click here to purchase tickets. Millbrook Winery is one of more than a dozen stops on the Dutchess Tourism Taste Finder Craft Beverage Trail, through which you can unlock special offers – including free flights, pints and custom glassware – at participating breweries, distilleries, wineries, meaderies and cideries throughout Dutchess. Click here to learn more about “The Pass to Fill Your Glass!” 

Related: A First-Timer's Guide to Dutchess County 

“Symphonie Fantastique” 

Saturday and Sunday, Feb. 11 and 12 at the Fisher Center, Bard College, Annandale-on-Hudson 

Conductor Leon Botstein, pianist Evren Ozel and The Orchestra Now open the 2023 season on a romantic note with a concert featuring “Symphonie Fantastique” – Berlioz’s epic tale of an artist’s passion for a beautiful woman – as well as Henselt’s “Piano Concerto” and Weber’s “Der Freischutz” Overture. To reserve tickets, click here. The Fisher Center is another location on the Dutchess Tourism Inspiration Finder Arts and Culture Trail. 

“Sweet Violets” at Starr Cinema 

Sunday, Feb. 12, 1:15 p.m. at Upstate Films’ Starr Cinema, Rhinebeck 

This free screening of filmmaker Tobe Carey’s 2012 documentary will teach you all about a little-known piece of Rhinebeck history known as the Violet Boom. The violet was the world’s most coveted flower and a symbol of the height of fashion from the Gilded Age through the Great Depression, and Rhinebeck was the Violet Capital of the World. Carey will be on hand to introduce the film, which features vintage photos and postcards and rare film footage, along with interviews with historians and commercial growers. Stick around after the film for a Q and A with Carey. To reserve your seats, click here. Upstate Films is another participant on the Dutchess Tourism Inspiration Finder Arts and Culture Trail.

Related: Top 10 Local Shops for Book Lovers 

Towne Crier Cafe
Towne Crier Cafe, Beacon

Beacon Rising Choir 

Sunday, Feb. 12, 2 p.m. at the Towne Crier Café, Beacon 

Get ready for a powerful and artistic performance featuring a variety of styles and genres as the Beacon Rising Choir returns to the Towne Crier Café for the first time in three years. The choir’s selections highlight many female, LGBTQIA+ and BBIAPOC composers and their messages of social justice, compassionate community and radical self-love. To purchase tickets, click here. This performance will serve as a fundraiser for the Compass Arts Creativity Project, whose mission is to create healthy, just, equitable and resilient communities through the arts. 

Used Grooves 

Tuesday, Feb. 14, 10 a.m.-8 p.m. at Darkside Records, Poughkeepsie 

If your Valentine is a music lover who is partial to vinyl, cassettes or CDs, you are in luck! Valentine’s Day this year falls on a Tuesday, which is also “Used Tues for Yous” at Darkside Records. Stop in at the Hudson Valley’s largest independent music store and browse through a fresh batch of already-loved music, movies and more in all your favorite formats. There are new arrivals every Tuesday. 



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