Festive Fun and Holiday Shopping Around Westchester County


Holiday shopping and celebrations may be different this year, but no worries! Westchester County Mom has got you covered!

Although venues may have changed and ventures may be socially distant, there’s still tons of fun to be had and purchases to be made for everyone on your holiday lists. 

Holiday Experiences

Pop-Up Ice Skating Rink

‘Tis the season to ice skate! Skate all holiday season at the Pop-Up Ice Skating Rink located at the Cross County Shopping Center in Yonkers. The pop-up rink is not real ice but is a smooth “glice” material, which is great for young and first-time skaters. Real ice skates are worn, gliding slightly slower on glice (plus it’s not as cold!). Admission is $10 for a one-hour session and includes skates. Strict COVID-19 safety protocols are followed. For a real New York, holiday experience take a look at the NEW 44 foot tall Christmas tree, grab a bite at the Holiday Food Truck Market and take Photos with Santa. See Cross County Events for all dates and times.

Westchester Winter Wonderland

The annual Winter Wonderland at the Kensico Dam Plaza looks different for 2020. This year, the venue offers a 1.2-mile Drive-Thru Holiday Lights Extravaganza filled with thousands of lights! Following along a driven path, the attractions include elves Ned and Albert, glittering angels of peace, a 50-foot dove, festive holiday music, dancing trees, glowing snowballs, candy cane lane, a spectacular 100-foot light tunnel, Westchester’s favorite 40-foot Christmas tree – and of course, for the grand finale, Santa Claus greets every car. Purchase tickets in advance at $25 per car. Open every night from November 27 – January 3 **Except: Nov 30, Dec 7, Dec 14, Dec 24 (Christmas Eve), Dec 25 (Christmas Day)

Holiday Shopping

White Plains Holiday Market 

Features 40+ vendors and artisans in individual open-air booths in the heart of downtown White Plains on Waller Avenue (between Maple Avenue and Lyon Place). Pick up your Christmas tree or holiday decorations! Discover interesting and unique gifts for everyone on your holiday shopping list. When you’re all tuckered out from shopping, head into one of the many close-by downtown restaurants for a drink and a bite to eat.

There is no cost to enter. The holiday market runs from December 3rd through December 13th (Thursday-Saturday: 11 a.m. – 9 p.m.; Sunday-Wednesday: 11 a.m. – 7 p.m.).  Wednesday, December 9th, will be a Day of Giving. A percentage of sales will be donated to Snarr Northeast animal rescue and Friends of White Plains Public Schools. Masks and social distancing are required.

Online Artisan Boutique 

This boutique is organized by the Rye Arts Center. It gives you the opportunity to enjoy a curated online shopping experience while supporting small businesses and the arts. Get a head start on holiday shopping, find unique treasures to brighten your home, or treat yourself to jewelry, spirits, clothing, and more! The boutique runs from Monday, November 23rd – Tuesday, December 1st. A portion of proceeds will support The Rye Arts Center’s outreach activities. Every treat you purchase will treat the community to scholarships, after-school programs, and more.

Chappaqua Craft Fair

2020 marks the 36th anniversary of the Chappaqua Craft & Gift Fair. What started as a small school event, this craft and gift fair, has grown into an annual holiday shopping experience. Due to COVID-19, the fair will be fully virtual yet still able to provide our community with incredible gift ideas from local, small businesses and talented artisans. Vendors include handmade jewelry from Bekaluna Designs, handpicked gift arrangements from Beneboon, baked goods from Flour.Sugar.Love and many, many more. Shop on-line all November! As a non-profit 501c3, the Chappaqua Craft and Gift Fair is the largest fundraising event held by the Robert E. Bell PTA.

The best aspect of all this fun and shopping is that we’re contributing to local charities and supporting local vendors. These events and many more are listed on our Westchester County Mom Events Calendar!

What other local holiday events are you attending?

Please feel free to submit them here.

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Melissa Jacobowitz is a Bronx native who moved to Westchester County after she and her high school sweetheart got hitched in 1997. She and her husband live in Mount Kisco with their son Corey (b 2004) and daughter Mia (b 2007). Melissa spent many years working in Human Resources and currently works in enrollment and marketing for a child care organization. Melissa is a two-time survivor of Postpartum OCD. Melissa initially became interested in writing to raise awareness for perinatal mood and anxiety disorders, but has discovered that writing is a newfound aspect of her life that she thoroughly enjoys. She was also a contributing writer with Suburban Misfit Mom and you can find her stories at http://suburbanmisfitmom.com/writer/melissa-jacobowitz/ Melissa is also a featured writer in the book “A Dark Secret,” which is a compilation of where 15 women share their stories of maternal mental illness from diagnosis to recovery. Melissa is excited to write with the Westchester County Mom team and hopes that you’ll enjoy her stories of the trials and tribulations of a born-n-raised city girl raising a teenagers growing up here in Westchester.