• Loving Westchester
  • Posts
  • 💗 Loving Westchester's Winter Wonders: Frosty, Lights & Trains Return While New Traditions Debut

💗 Loving Westchester's Winter Wonders: Frosty, Lights & Trains Return While New Traditions Debut

Plus, an easy guide to Santa's whereabouts this weekend.

Author

Wes+Bec Willetts
November 28, 2025

Happy Friday, Westchester!

 

We’re hoping most of you are getting to enjoy a long weekend or at least the memories of delicious food and good company yesterday are getting you through to more merriment this weekend! Did Aunt Joan drink too much and tell her sister’s husband what she really thought of him? Did you have to pretend that someone didn’t overcook the turkey, making up for it with lashings of gravy? Did you have too many helpings and are now hoping to work it all off and be good before the next big wave of festive treats? Whatever you did, we hope it was what you wanted, with some laughs thrown in for good measure. Life is short after all.

 

Now the time is yours, and there’s plenty to do. So take those ‘gather’ vibes and bring them into the weekend with you.

 

Bec+Wes

 

 

In today’s edition:

  • Featured events… Rye gets a brand-new tradition and official holiday cookie, Armonk celebrates its Frosty heritage, and the biggest ever LEGO set donation kicks off.

  • Kid-friendly fun… enjoy a lit-up Wonderland from the comfort of your car, go see trees all aglow, bid on tabletop versions, or experience a train-lovers dream.

  • Grown ups & date nights… If you can’t find Jessie’s Girl, laugh it off at a brewery open mic night, check out some comedic talent in Port Chester or go catch a Cannes Award winner in Pleasantville.

  • Live music beat… nine great gigs to get you shmoozin’ and groovin’

  • Westchester’s weekend Santa sightings… our handy, go-to guide of where to catch Old St. Nick this weekend for your little ones.

  • Worth a drive… snowball fights without the mess, a fairground of more than one million lights, and a reindeer festival just a stone’s throw away.

Plus, a message from our partners, QueenBHive (for all things brand and marketing) & QueenBPoker (for all things fun and play!)

 

If you would like to chat with us about advertising in Loving Westchester, shoot us an e-mail at [email protected]. We love supporting local businesses and events!

 

Let’s go!

💓 The Pulse

Loving Westchester’s Featured Events!

Sat., Nov 29 | Wainwright House, Rye | 4-6p | Donations from $10pp

 

A sweet, new tradition at Wainwright House kicks off with a festive evening. Explore whimsical gingerbread creations from local bakers, sip hot cocoa, enjoy holiday music, and witness Mayor Josh Cohn unveil the Official Cookie of Rye, the Chocolate Rye Cookie, created to support Cookies for Kids’ Cancer.

 

The Showcase (and competition) is at the heart of Wainwright’s December programming, with special events running around it throughout the month. Guests are encouraged to bring non-perishable donations for Feeding Westchester.

 

Runs through Dec 31 | LEGOLAND Discovery Center, Yonkers | Times Vary | Tickets from $24.99

 

Leave the winter chill behind and enjoy some festive family fun at LEGOLAND’s Bricktacular. Snap photos with epic holiday builds, explore seasonal lands and scenes, make ornaments and Gingerbread Man creations and even meet the LEGO® Gingerbread character. Plus, build a LEGO heart for the Build To Give donation drive and take part in the biggest ever donation of LEGO sets to children in need.

 

Sun., Nov 30 | Armonk | From noon, parade at 4p | Free

 

Armonk highlights Frosty The Snowman’s roots with an afternoon of miniature train rides, wagon rides, dancers, bands, Santa visits, face painting, cookie-decorating, and make-your-own Frosty crafts before everyone joins the Frosty Parade up Main Street to Wampus Brook Park. The day is in celebration of Armonk’s connection to lyricist Steve Nelson, who wrote “Frosty the Snowman” while living there. If you’ve any jackets or hats you can also support the Help Frosty Help Others Winter Warmth drive while in town.

Partnered With QueenBHive

Want your brand to stand out?

We help brands cut through the noise.

With decades of experience running communications and partnerships for worldwide names, QueenBHive brings global experience to local businesses. Whether you’re stuck on what to post, how to grow, or how to sound like you online, QueenBHive makes it make sense.

 

With support and packages designed for businesses of all sizes, including help with visuals, content and PR, we take the stress out of building your brand.

 

Based in Westchester and proud to be part of this community.

 

🐝 Visit QueenBHive.com or email us here. Our flexible and friendly approach will help you figure out exactly what you need to grow with confidence.

📆 What’s Happening?

 

Kid-friendly Fun!

Fri., Nov 28 | Westchester Children’s Museum, Rye | 10a-5p | Included with admission

 

Visit Rye’s Westchester Children’s Museum for some Thanksgiving festivities on Sound Shore featuring holiday-themed story times throughout the day and crafts at the Makerspace.

 

🎄 Chappaqua Tree Lighting

Fri., Nov 28 | 100 King St., Chappaqua | 4-5p

 

Head to Chappaqua’s Horace Greeley House as the holiday season kicks off with the town’s annual tree lighting. Fill up on cookies and hot chocolate, listen to caroling from The Greeley Enchords and get a glimpse of Santa! He’s a busy guy this weekend!

 

Begins Fri., Nov 28 | Kensico Dam Plaza, Valhalla | Check link for times & tickets

 

Pack the kids up and be prepared for some excited ‘ooh’s and ‘aah’s as Westchester Parks Foundation’s 1.2-mile Winter Wonderland Drive-Thru takes you through a 100-foot light tunnel, Rudolph’s Runway and Candy Cane Lane, as well as a special sighting of the man of the moment! Truly a wonderful experience for all the family, if not purely just for your own inner child!

 

Fri., Nov 28 | Westchester County Center, White Plains | 7p

 

The Westchester Knicks are home for the holidays, hosting the Maine Celtics Friday night at the Westchester County Center.

 

Select dates through Dec 30 | Harvest Moon Farm & Orchard, North Salem | Check link for available times & tickets

 

Reminder that Harvest Moon’s Lumina holiday attraction is open and running Fri through Sun this weekend for those looking to burn off some excess calories from Thanksgiving dinner and catch half a million shining lights while doing it.

 

Starting Sat., Nov 29 and running to Dec 31 | Lasdon Park, Katonah | Timed entry: $20 adults / $10 kids / $15 seniors

 

Lasdon’s signature holiday experience is back with a fully re-imagined, more immersive holiday experience and train show. Enjoy multi-level, G-scale trains running across 2,500 square feet of bridges, tunnels, waterfalls, and festive scenes amidst holiday displays, and grab a slice from George’s Wood Fire Pizza. Santa will also be making an appearance on select dates.

 

Sun., Nov 30 | 12–3p | Rye Historical Society | Free

 

Stop by the Square House for festive music, hot chocolate, kids’ activities, Santa visits, crafts, and the annual Tabletop Tree Fundraiser. Bid on one-of-a-kind themed trees created by local designers (silent auction starts at $125) and vote for favorites. Meals on Main Street will be on hand to collect non-perishable food donations.

 

Grown Ups & Date Nights

Fri., Nov 28 | Tarrytown Music Hall | 8p | Tickets from $44.50

 

The THE BAND Band pays tribute to the legendary, Thanksgiving night farewell concert The Last Waltz from Rock and Roll Hall of Famers, The Band. Joining them on stage is fiddle player Larry Packer, who played alongside the star-studded lineup in 1976.

 

Sat., Nov 29 | Jacob Burns Film Center, Pleasantville | 1p | Tickets from $20

 

Pleasantville’s Jacob Burns Film Center hosts a screening of 2025 Cannes Film Festival Palme d’Or winner It Was Just an Accident this Saturday afternoon, featuring a Q&A with director Jafar Panahi.

 

Sat., Nov 29 | The Capitol Theatre, Port Chester | 8p | Tickets from $45.65

 

Eighties tribute group Jessie’s Girl takes The Cap stage on Saturday night, bringing its high-energy throwback show to Port Chester backed by top NYC vocalists and musicians. The show kicks off with openers The Fresh Kids of Bel-Air.

 

😂 Westchester Weekend Comedy Scene:

  • TriState Stand Up… showcase feat. Cody Clarke, Umar Pasha, Whitney Allen, Andrew Alfredo & Chris Warren | Sun., Nov 30 | Run & Hide Brewing Co., Port Chester | 5p

  • TriState Stand Up… open mic night | Sun., Nov 30 | Wolf & Warrior Brewing Company, White Plains | 6p | $10 bar tab minimum

 

 

The Beat

Westchester’s Live Music Scene

Thanks to our partner, QueenBPoker!

 

Go All In with a Special Event This Season

 

Whether it’s a casual home game, a corporate celebration, a beginners' poker evening or a night that gives back — QueenBHive Poker delivers unforgettable poker and gaming experiences.

No experience needed; we’ll teach, host, and handle every detail.

 

Choose an event with a difference. Plan your game night with us!

 

Contact us here for more details.

 

🎅 Westchester’s Weekend Santa Sightings!

 

🚗 Worth a Drive

There are also great things going on outside Westchester county lines this coming week

Select dates now through Jan 4 | The Bronx Zoo | Check link for times & tickets

 

The Bronx Zoo’s annual Holiday Lights attraction is back with millions of lights and hundreds of illuminated animals to uncover along six zoo trails! New this year are snow tube slides, an ice-themed throne and virtual snowball throwing.

 

Select dates now through Dec 28 | Dutchess County Fairgrounds, Rhinebeck | Check link for times & tickets

 

The Wonderland of Lights drive-thru light show is now open for its 5th year at Rhinebeck’s Dutchess County Fairgrounds. Catch hundreds of illuminated displays made up of more than one million lights!

 

Nov 28 through Dec 24 (closed Sundays) | Sam Bridge Nursery & Greenhouses, 437 North Street, Greenwich, CT | Check link for daily schedules & photo prices

 

Santa and three of his real-life reindeer drop by Sam Bridge Nursery & Greenhouses in Greenwich for a photo meet and greet with tons of other contests and entertainment scheduled for guests. A portion of all photo proceeds will support the charity Kids in Crisis.

Thanks for reading Loving Westchester!

 

We’re really enjoying putting this together twice a week and hope you enjoy reading it. We’ve said it before and we’ll say it again… we love to hear from you! You can reach us at [email protected].

 

Check us out on Instagram for additional highlights outside of our normal Tuesday & Friday e-mails and, as always, please send this along to a friend who’s always asking, “What’s going on this week?”

 

Until next time,