7 Unique Date Ideas in Westchester County

From a paint and sip class to an afternoon museum visit, these date ideas are sure to excite in Westchester.

Whether you and your partner have been together for years or your first date is approaching, consider adding a twist to the traditional dinner date. While dining at a wine bar or chatting over a cup of coffee is undoubtedly delightful, Westchester has a lot of options for the dating scene. Allow us to present six unique date ideas around the county when dinner and a movie seems a bit overplayed.

Paint and Sip

A date night provides an excellent opportunity to showcase your creative talent. Westchester studios host regular paint and sip classes and events on weekday nights and weekends, including A Maze In Pottery in Briarcliff and Muse Paintbar in White Plains and Yonkers. Other studios included on our list offer additional crafty activities like stoneware pottery and terrarium building. Many of the local sip and paint classes allow painters to bring alcoholic beverages as well.


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Visit a Museum

A classic museum date should be in the books for you and your partner. Hitting up a local museum and diving into our county’s rich history and culture sounds like an ideal Saturday afternoon. The Hudson River Museum in Yonkers checks off all the boxes as it displays over 100 years of history and has a planetarium, art galleries, and plenty of events. If your date only has eyes for the arts, head over to the Katonah Museum of Art, one of the most celebrated small museums in the country. The KMA normally displays three to four major exhibitions each year with a unique offering at each one.

For more information on admission and hours, check out our local museum guide.

Go Rock Climbing

If you are an active couple, there’s nothing like a day of rock climbing to strengthen your bond. Movement at Valhalla (formerly The Cliffs) offers day passes for $22, which includes access to the climbing gym, fitness areas, and locker rooms. You can add a chalk bag for $2, harness for $4, climbing shoes for $6, and staff assistance for $8. Dip your hands in some chalk and race to the top, or see which partner has those solo climbing skills. Movement is a welcoming environment for both beginners and climbing pros.


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Rock out at a Concert

Westchester County is a hotspot for musicians, making a concert or comedy show a standout date. Our winter concert roundup highlights a handful of concerts happening through February. There are some big names heading to the 914, including Portugal. The Man, Pete Davidson, and Dionne Warwick. For additional shows, check out the websites of local venues: Tarrytown Music Hall, The Capitol Theatre, Paramount Hudson Valley Theatre, and Caramoor.


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Attend a Sports Game

Why make the trek to Madison Square Garden when we have our own Knicks team right here in Westchester County? The Westchester Knicks, the official NBA G league affiliate of the New York Knicks, play their games at Westchester County Center and make for a slam dunk of a date. Purchase tickets here.


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Go Thrifting

A thrifting date is all the rage nowadays. Throw on your best fit, grab a coffee or tea, and search the racks for THE perfect piece of clothing. Fantastic Finds is a thrift store in Chappaqua that sells clothing, jewelry, scarves, and other secondhand items. Trilogy Consignment, on Tarrytown’s Main Street, is a must-visit for quirky, vintage items. Check out our consignment store guide for more stores to scope out in the county.

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Take a Day Trip

Now, if you’ve exhausted all date options in Westchester and are looking to branch out, Amtrak allows you to explore the Hudson Valley hassle-free. A train ride to the vibrant city of Hudson is only an hour and 15 minutes, while Poughkeepsie is 45 minutes. For additional locations and exploration checkpoints, head to our Amtrak day trip and weekend getaway guide.


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Related: The Official Valentine’s Day Dining Guide for Westchester County

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