Holiday Happenings in and around Westchester! - Rye & Rye Brook Moms

Winter and the holiday season are a wonderful time of year! But sometimes there’s so much going on, that it becomes overwhelming to plan this special time with our families!

That is why Rye & Rye Brook Moms has organized all the best activities in Westchester and the surrounding areas into one, easy to follow guide!

Brought to you by our partner, French-American School of New York (FASNY), we are excited to present the RYE AND RYE BROOK MOMS HOLIDAY GUIDE – Your one stop guide to the best winter activities in the area for you and the whole family!

Founded in 1980 as a one-classroom preschool, the French-American School of New York (FASNY) has offered the best in bilingual education for local families and expatriate students for more than forty years. In those 40+ years, FASNY has evolved to become an international and bilingual N-12 day school educating more than 700 students on three campuses in Mamaroneck and Larchmont, New York.

It is the only school in the New York metropolitan area accredited to offer both the International Baccalaureate (IB) diploma and the French baccalaureate and now offers an International Program for grades 1-8 with no previous French required.

Virtual Open Houses
Pre and Lower School – November 29, 6pm
Middle and High School – November 30, 6pm

914-250-0401, [email protected]
Or Click here for admission and more information


The magic is back! After a two-year hiatus, the Rye Chamber of Commerce is again hosting Mistletoe Magic. This downtown holiday family fun event will take place on the Sunday after Thanksgiving. Purchase Street will become a pedestrian only plaza, filled with fun activities, crafts, games, and performers for the entire family.


November 28, 12pm – 3pm
Purchase Street, Rye, NY
More Details

Holiday Lights at Crawford Park


Saturday, December 4th 4pm-8pm
Crawford Mansion Community Center
122 North Ridge Street, Rye Brook

Family Friendly Open House

Food Trucks, games, holiday train rides, crafts by Westchester Children’s Museum and musical performances by Westchester Chordsmen, Blind Brook Middle & Hight School Bands, Port Chester High School Brass Ensemble and more.


Christmas Tree Lighting Ceremony

December 2, 2021
Starts at 6PM

Downtown at the police booth – Main Street, Port Chester

Mayor will light the tree

Music by PC brass ensamble & PC HS Choir
Free hot chocolate

Rye Brook Recreation Winterfest

Friday, December 3rd 6:00pm-9:00pm
Pine Ridge Park

Santa in the Park
Crafts and Games
Ice Carving Demos
Winter Themed Obstacle Course
Train Rides, Santa and Elf Magic Show
Christmas Tree & Menorah Lighting

**Coats will be accepted for Paula’s Pals to be distributed to less fortunate locals.

Port Chester’s Christmas Parade

December 11, 2021
At 3:30 PM

Parade Route from King Street School along King Street and ends in Lyon Park

Santa will hand out gifts after the parade in Lyon Park

Port Chester Fire Department

December 18, 2021
Starts at 11am

The PCFD Will be giving Santa a Ride through Port Chester and Rye Brook during his visit!

Celebrate Chanukah with Chabad of Greenwich

Celebrate Chanukah with Chabad of Greenwich with a Car Menorah Parade, Grand Menorah Lighting on Greenwich Avenue, Chanukah Concert, Gelt Drop, Donuts and drinks and fun for all ages! Parking will be available alone Greenwich Avenue.

December 5
Register at

Chanukah Extravaganza: Fire on Ice

Join Chabad of the Rivertowns at the waterfront park in Dobbs Ferry for “Fire on Ice.” Watch the fastest ice carver in Guinness world record carve a giant Ice Menorah. Enjoy a dazzling fire show, and Epic Gelt drop and delicious Latkes and donuts. Something for everyone! RSVP appreciated. 

Sunday, Nov. 28, 4pm
Dobbs Ferry Waterfront Park, 87 Ogden Park, Dobbs Ferry
Watch the fastest ice carver in Guinness world record carve a giant Ice Menorah. Enjoy a dazzling fire show, and Epic Gelt drop and delicious Latkes and donuts.



Santa and his LIVE reindeer – Dancer, Dasher and Prancer – are returning to Greenwich for the 13th Annual Greenwich Reindeer Festival & Santa’s Workshop presented by Jenny Allen/Compass. The cherished town tradition continues for the thirteenth consecutive year at this expansive nursery where visitors can have their photo taken with Santa, meet the reindeer and also enjoy the new Santa’s Workshop, which provides more space for families while they wait in line for their photo with Santa. This all takes place just minutes from downtown Greenwich. Parking is free.

November 26 – December 24
Sam Bridge Nursery & Greenhouses, 437 North Street

Menorah Lighting at The Cross County Center

We will be lighting the menorah with the Chabad of Yonkers on Monday, November 29th at 6pm. Enjoy live music, cultural dancing and delicious treats!

The menorah will be located near H&M and Forever 21. 

Happy Chanukah to all those who celebrate!

Menorah Lighting at Ridge Hill

Join Ridge Hill and Chabad of Yonkers for a Chanukah Celebration on Sunday, November 28!

Event begins at 4PM and Menorah Lighting is at 4:30PM

Enjoy music from Mr. Shabbos, Chanukah Treats, and a Gelt Drop!!

Find us in Town Square near The Cheesecake Factory

The White Plains Annual Holiday Market

Court Street between Main Street and Martine Avenue
December 5 – 19 , 11am – 7pm daily

The White Plains annual Holiday Market is a 15-day shopping experience in the heart of downtown White Plains!
The Market will feature 60+ artisanal vendors from around the Westchester County region. Pick up your Christmas tree or holiday wreath and find interesting and unique gifts for everyone on your holiday shopping list!  


A Christmas Carol The Musical

White Plains Performing Arts Center

December 3-30 2:00pm & 7:00pm

A Charlie Brown Christmas LIVE ON STAGE


December 3rd 7pm-8:30pm
Chappaqua Performing Arts Center

The show is 90 minutes including intermission.


Please review covid policy at time of purchase

Watch “The Polar Express 4D Experience,” a fun condensed version of the Warner Bros. film where you view the movie in 3D, and experience special sensory in-theater effects like snow, wind, the aroma of hot cocoa, and more.

Fri., Nov. 26 (the day after Thanksgiving) and will play daily through Jan. 2.
Maritime Aquarium, 10 N Water St, Norwalk, CT 06854

Rudolph the Red-Nosed Reindeer: The Musical

The “most famous reindeer of all” is coming to Stamford on November 27! Kick off the holiday season and enjoy a day of family fun when Rudolph the Red-Nosed Reindeer: The Musical comes to The Palace Theatre

November 27
Palace Theatre, 61 Atlantic St, Stamford
More Details

Ice Skating

Ice Skating at The Cross County Center

The pop-up ice rink, located at Center Court near the Christmas tree, is not real ice, but is a smooth “glice” material, great for young and first time skaters. We wear real ice skates, but glide a little slower than on real ice (plus it’s not as cold!).

Admission is $10 and includes skates and a one hour session. Character skate nights will take place throughout the season. Debit/Credit only – no cash accepted. Must be 5 years or 42 inches tall. Reservations are not needed in advance.

To book a private event at the pop-up ice rink, such as a birthday party or other event, please CLICK HERE.


Ice Skating at Dorothy Hamill Skating Rink

Dorothy Hamill is a Town-owned ice rink that is open from early September through mid-March. The Rink offers a variety of ice skating activities and programs for all ages.

November 26-December 24
Dorothy Hamill Skating Rink, Sue Merz Way, Greewich

Holiday Lights

Join us for a family holiday festival at the Bronx Zoo. During the evenings, the park comes to life with holiday cheer as immersive light displays, custom-designed animal lanterns and animated light shows sparkle across the zoo. The outdoor celebration is complete with festive entertainment, seasonal treats and classic holiday music. The walk-through experience is a beloved tradition, enchanting and fun for all ages.

Now through January 9; Select Dates
Bronx Zoo, 2300 Southern Boulevard, Bronx, NY

LUMAGICA brings a maze of lights. With over 500,000 LED bulbs, it’s the biggest light park in Westchester and Putnam County. A true light experience at Harvest Moon. Guests will experience LUMAGICA as a walking tour through a magical forest full of marvelous animal structures and festive decorations, all brilliantly illuminated by over 500,000 LED lights. Harvest Moon’s orchard will be transformed into a radiant fantasy sure to delight guests of all ages!

Tickets are available every Friday, Saturday, and Sunday beginning Friday, November 26th through Sunday, December 12th. Beginning Friday, December 17th, tickets will be available every day through December 23rd. Then again, beginning December 26th through December 30th.

November 26 – December 30
Harvest Moon, 130 Hardscrabble Road, North Salem, NY 10560

Holiday Stroll is a new holiday tradition located at Mill River Park in Downtown Stamford, CT. A stroll through a festive, dazzling word of larger than life holiday light displays. After strolling enjoy our Holiday Village featuring a state-of-the-art Christmas Tree, holiday music, tasty food vendors, and the Half Full winter beer garden.

November 26 – January 9
Mill River Park, Stamford, CT

Westchester’s Winter Wonderland Drive-Thru Holiday Light Extravaganza, presented by Westchester Medical Center Health Network, will return to Kensico Dam Plaza bigger and better than ever with thousands of more lights, magical holiday animations and a live Santa! Guests will be dazzled and delighted along the 1.2 miles of holiday lights with new Elf Disco, a whimsical display of jubilant children from around the world, a breathtaking Peace on Earth LED display with animated trumpets and angels, and two new thirty-foot snowflakes to light up the largest holiday Christmas tree in Westchester! And if that is not enough, there is also a bigger and better snowstorm central that the whole family can enjoy right from the warmth and safety of your own car!

November 26 – January 2
Kensico Dam Plaza, 1 Bronx River Pkwy, Valhalla, NY

Train Shows

This beloved tradition returns for its 30th year with a miniature wonderland in the warmth of the Enid A. Haupt Conservatory. Marvel at model trains zipping through an enchanting display of more than 175 famous New York landmarks—imagine the Statue of Liberty, Brooklyn Bridge, Rockefeller Center, and other favorites—each delightfully re-created from natural materials such as pine cones, acorns, and seeds.

You’ll also discover a showcase of our very own New York Botanical Garden buildings such as the iconic Haupt Conservatory and—new for this year—the majestic LuEsther T. Mertz Library Building, both designated New York City landmarks.

November 20 – January 23
New York Botanical Garden, 2900 Southern Boulevard, Bronx, NY

Holiday on the Hill Train Show

Lasdon Holiday on the Hill Train Show at Lasdon Park in Katonah has expanded to more than 5,000 square feet of indoor and outdoor exhibit space. Your experience begins with a stroll through whimsical holiday exhibits leading to the Conservatory. Once inside, you will see trains chugging along on nine multi-level tracks, over bridges, under tunnels, through quaint holiday scenes and colorful seasonal plants!

Santa will be available to meet with children in his Holiday Cottage located opposite the Conservatory at scheduled times during each session.  Visits with Santa are only available as space and time permits.


Photos with Santa

Santa Photos at The Cross County Center

Santa will be available for photos and visits in his workshop, located in the former NY&CO store, across from Michael Kors.

MAKE YOUR RESERVATION HERE. Reservations are strongly recommended, but not required.

We are taking all precautions to ensure you have a safe and magical experience, including:

  • Santa’s Workshop is cleaned throughout each day, with CDC approved products and procedures
  • Santa and staff are vaccinated and/or tested for COVID-19 regularly
  • Masks are strongly recommended for unvaccinated guests, but may be removed for the purpose of the photo
  • Hand sanitizer stations are available at the entrance and exit 


  • SUNDAYS: 1PM – 6PM
  • MONDAY & TUESDAY 11/22-11/23, 2PM – 7PM
  • MONDAY – THURSDAY, 11/29-12/23, 11AM – 8PM
  • FRIDAY, 11/19, 11AM – 7PM
  • FRIDAYS, 11/26-12/23, 11AM – 8PM
  • SATURDAY, 11/20, 11AM – 7PM
  • SATURDAYS, 11/27-12/18, 11AM – 8PM

Pet Photos with Santa

Bring your dogs and cats for Pet Photos with Santa! Santa’s Workshop is located inside the former NY&CO store, next to Footlocker and across from Michael Kors.

No reservation is needed – just attend during one of these two event dates:

  • December 6, 6pm – 8pm
  • December 13, 6pm – 8pm

Dogs must be kept on a leash and cats in a carrier until photo time. Please come prepared to manage any ‘accidents’ with your pet. Dogs, cats, bunnies only – no exotic animals (such as snakes, lizards, etc. permitted). Click for more details.


The ultimate holiday tradition is back: Photos with Santa! Reservations are necessary.

November 12 – December 24
The Westchester, 125 Westchester Ave, White Plains, NY
More Details

Photos with Santa at Ridge Hill

November 26 – December 24

Located at the corner of Market Street and Archer Avenue, across from Apple, Santa will be available daily for visits and photos.

CLICK HERE for reservations (recommended but not required).


  • Santa is vaccinated and will wear a mask upon request. All staff will be masked. Guests are required to wear masks but may remove them for the photo.
  • Santa and staff will undergo daily temperature checks and symptom-screening protocols.
  • A thorough cleaning of the set will be completed each evening and twice during operation hours.
  • Reservations are recommended and have priority. Walk-ins will be accepted but worked into the line as time permits.

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