20 Date Ideas and Romantic Experiences in the Hudson Valley

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

When it comes to date ideas, the Hudson Valley offers so many opportunities. Whether you’re looking for a special to-do for Valentine’s Day or an anniversary or want to treat your sweetie to a fun outing, these activities will get you started.

– 1 –

Explore shops and eateries on our many Main Streets, like those in Saugerties, Cold Spring, 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.

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– 3 –

Discover your inner artist at Eat. Paint. Love. in Beacon or Wallkill River Center for the Arts. 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.

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– 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 It Happened One Night screening on Valentine’s Day features a dessert reception with Analog on Hudson’s Photo Booth for an exciting portrait.

– 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.

– 19 –

Join Juckas Riding Stables in Pine Bush for a romantic date night trail ride.

–  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

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