How to Spend a Romantic Valentine’s Day Weekend in Westchester

Drobot Dean | AdobeStock

All the sweetest local events and happenings to show your sweetie how much you care during the most amorous holiday of the year. 

With Valentine’s Day falling on a Sunday this year, Westchester’s residents can look forward to a whole weekend of romantic escapades.

If you’ve already made your reservations and picked out your favorite local chocolates, here are a few more great ideas to show your special person just how much they mean to you.

Read More: Westchester Magazine’s Valentine’s Day Guide

Friday, February 12

Feel like going shopping for some cute gifts and nibbles? (914) PopUps will be hosting a series of small vendors starting this Friday and running all weekend long at The Westchester in White Plains. Grab something cute to wear from J’Aime, pick up home spa supplies from Scentfluence and the copper faucet, or just snag a sensual snack of vegan chocolates from Olenkos Kitchen. (Then head home to try out all your new goodies!)

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For a more aural experience, support the White Plains Performing Arts Center by streaming Jim Brickman’s ‘Share the Love’ live at 9 p.m., with follow-up performances at 7 p.m. and 10 p.m. on Saturday and Sunday. Tickets are $50, with a portion of the proceeds benefiting WPPAC.

Jim Brickman - WPPAC
Courtesy White Plains Performing Arts Center

Alternately, you can tune into Livingston Taylor live from the Emelin Theatre starting at 8 p.m. for just $25. More of a live (virtual) theater kind of household? Chill Bucket’s Annual Valentine’s Cabaret also runs all weekend, beginning at 8 p.m. Tickets are pay-what-you-want starting at $10.

Miss date night at the movies? Showcase Cinema de Lux at Ridge Hill is booking Valentine’s Day Private Screenings starting at $99. Enjoy sodas, snacks, and romantic classics like The Bodyguard, Casablanca, Crazy Stupid Love, or The Notebook (or take in Magic Mike, we’re not judging).

Saturday, February 13

Forgot to buy a card? The Rye Arts Center has you covered with its in-person Pop-up Card Making Workshop starting at 10 a.m. Space is limited and spots are $25. Want to get the kids in on the holiday fun? The Westchester Children’s Museum is hosting Cupid’s Color Lab — part Valentine making, part chemistry experiment — where kids ages 4 to 8 and their families can make some truly unique cards for someone special. The event is free, but space is limited. 

Pop-up Valentines
Courtesy Rye Arts Center

Center yourselves in mind and body with Yoga for Charity, a local event started by Brian and Alka Kaminer’s virtual yoga studio, Present Wisdom. The 75-minute online class will help get you balanced and limber for just $10, while also helping a great cause; all proceeds go directly to St. Jude’s Children’s Research Hospital. Every additional $5 donation can also win you great local door prizes like St. Jude’s swag, free yoga classes, dinner for two at Moderne Barn or City Limits Diner, or gift cards to local shops like Hickory & Tweed and Athleta Scarsdale. Register online to sign up and donate.

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Can’t decide between a bottle of red or a bottle of white? Enjoy a Virtual Wine Tasting courtesy of the Lewisboro Library and South Salem Winery’s vintner John Vuolo. The $125 package includes a library tote stuffed with Chardonnay, Cabernet Franc, and Vidal Blank Ice, along with a wine stopper, chocolates, two long-stemmed roses, and plenty of snacks for a Zoom-along tasting and Q&A. Order online for package pickup at the library by 6 p.m. Friday.

Courtesy Lewisboro Library

Sunday, February 14

Maybe you should just put on some mood music and see where the spirit takes you? Starting at 3 p.m., the Stamford Symphony will stream “A Valentine from the Stamford Symphony,” featuring classical pieces by Bach, DeBussey, and even a special piece composed by the symphony’s own violinist Andrew Waggoner for his wife, cellist Caroline Stinson. The 30-minute online event is free, with no registration required to tune in, and will also include interview excerpts with symphony members. Alternately, Caramoor will stream Grammy-nominees

Imani & Catalyst
Courtesy Caramoor

Imani Winds and the Grammy-winning Catalyst Quartet all weekend long, for free!


Oh, the heck with it. Want to get married?

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No, really. Enough couples have had to postpone their nuptials this year and we think it’s high time someone did something about it. Luckily, Cortlandt Colonial Restaurant & Ballroom has teamed up with Magnifique Ceremonies to offer a one-day only pop-up wedding package starting at just $150.

Yes, you read that right. You can get married in a ballroom along with two witnesses and officiant, Champagne toast, and photos, all for less than the cost of a pair of mediocre earbuds. You can even enjoy dinner afterward at the restaurant! (Just make sure you have your marriage license first, so it’s on the up-and-up.) Call 917.375.1673 or email to schedule your 15-minute ceremony starting at 11 a.m.

Cortlandt Colonial Popup Weddings
Via Cortlandt Colonial


Looking for more great ways to share your love. Visit our Complete Guide to Valentine’s Day in Westchester.

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

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