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20 Great 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.

Dutch Ale House 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

Adobe Stock

– 2 –

Sample wine pairings of signature wines and high-quality chocolates at City Winery Hudson Valley on 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 –

Have some great beer (over 70 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 at home with virtual lessons through 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 live streamed concerts from Jazz Forum Arts in Tarrytown, Westchester’s only dedicated jazz club.

– 8 –

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

the falcon photo by Rafael Quirindongo. date ideas

The falcon photo by Rafael Quirindongo

– 9 –

Enjoy brunch and live music at in the “Falcon Underground” in The Falcon in Marlboro.

– 10 –

Take an online 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 –

Enter an online interactive art performance or watch a streamed concert at the Fisher Center for the Performing Arts. The Upstreaming Archives contain all previous shows with something for everyone’s tastes.


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– 13 –

Impress her or him with a date filled with art and athletics as you snowshoe or cross-country ski at Art Omi.

– 14 –

Get your toes tapping at an online celebration of The Flurry, one of the largest folk dance and music festivals in North America. Traditional dancing and music will bring culture to your weekend via Zoom.

– 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 in the virtual screening room of the Jacob Burns Film Center in Pleasantville.

– 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 via online livestream.

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 dine-in and takeout options for Valentine’s Day dinner, click here.

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

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