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20 Date Ideas and Romantic Experiences in the Hudson Valley

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Treat your special someone to a romantic night out or in with one of these unexpected, unforgettable dates along the Hudson River.

The Dutch photo by Simply Steph Photography; Cold Spring Apothecary photo by Chris Wesselman

– 1 –

Explore shops and eateries on our many Main Streets, like those in Saugerties (above left), Cold Spring (above right), Nyack, and Peekskill.

cheese and wine

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– 2 –

Sample signature wines and decadent dishes at City Winery Hudson Valley for Valentine’s Day.

– 3 –

Discover your inner artist at Eat. Paint. Love. in Beacon or the Wallkill River School of Art. Or have Grape Canvas Parties bring the paint and sip party to you.

Photo by Paul Halayko

– 4 –

Sip on great beer (dozens of styles to choose from), wine, and even cider at Newburgh Brewing Company.

Photo by Al Nowak

– 5 –

Celebrate historical power couples at the grounds of the FDR Estate (above) and Val-Kill in Hyde Park, and the scenic park of Olana State Historic Site in Hudson.

– 6 –

Take dance lessons with your loved one at Fred Astaire Dance Studio or Dojo Dance Company to experience the world of ballroom dancing.


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– 7 –

Hear and see established, emerging, and under-recognized artists with concerts from Jazz Forum Arts in Tarrytown, Westchester’s beloved jazz club.

– 8 –

See a concert or show from a historic theater like The Bardavon in Poughkeepsie.

the falcon photo by Rafael Quirindongo. date ideas

The Falcon photo by Rafael Quirindongo

– 9 –

Enjoy dinner and live music at The Falcon in Marlboro.

– 10 –

Take a cooking class and prepare meals like the chefs at The Culinary Institute of America.

– 11 –

Take an art day trip to Beacon where you can visit Dia Beacon via advance reservations.

– 12 –

Enjoy an art performance or watch a concert at the Fisher Center for the Performing Arts. Programming ranges from classical music to opera to theater, so there’s something for everyone.


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– 13 –

Impress your special someone with a date filled with art and athletics as you wander the expansive grounds at Art Omi in Ghent.

– 14 –

Embrace the giggles at Laugh It Up Comedy Club, located at Mahoney’s Irish Pub & Steakhouse in Poughkeepsie.

– 15 –

Go on a morning winter hike at one of the Hudson Valley’s gorgeous natural destinations.

date ideas

Photo courtesy of Jacob Burns Film Center

– 16 –

Take your date to see a classic feature or new release at the Jacob Burns Film Center in Pleasantville. The Roman Holiday screening on Valentine’s Day features gelato from Penny Lick Ice Cream Co.

– 17 –

Look for your favorite album from your teenage years or discover a vast selection of new vinyl at Darkside Records in Poughkeepsie.


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– 18 –

See a play or musical revue performed live at The Center for Performing Arts at Rhinebeck, then stick around for a day trip in town.

Date ideas

Photo by Steven Michael King

– 19 –

Join the Oz Farm Winter Riding Club in Saugerties for a private (or group) lesson.

–  20 –

Take a winter walk at Minnewaska State Park Preserve or Poet’s Walk Park in Red Hook, named in honor of Washington Irving and other literati who once strolled here.

For Valentine’s Day Dining in the Hudson Valley, click here.

Related: 9 Places to Take a Romantic Staycation in the Hudson Valley