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The Great Holiday Train Show!
06 Dec, 2025
Saturday
10:00 am
4:00 pm

The Great Holiday Train Show!

This beloved annual tradition returns to the New Castle Historical Society's Horace Greeley House for its fifth year. 2025 brings new featured layouts, including LEGO Around the World, alongside classic family favorites like the Polar Express and Santa’s Holiday Train. This unique holiday exhibition features something for the whole family. In addition to the trains, the rooms of the historic Horace Greeley House will be festively decorated for the season, with several full-sized holiday trees decorated by local designers. For those who are young or young at heart, we offer a train-themed scavenger hunt, an activity room with crafts and hands-on trains, and even a mini train engine for the perfect photo op! Stop by our shop before you leave for the perfect holiday gift.

100 King Street Chappaqua, NY 10514
The Great Holiday Train Show!
07 Dec, 2025
Sunday
10:00 am
4:00 pm

The Great Holiday Train Show!

This beloved annual tradition returns to the New Castle Historical Society's Horace Greeley House for its fifth year. 2025 brings new featured layouts, including LEGO Around the World, alongside classic family favorites like the Polar Express and Santa’s Holiday Train. This unique holiday exhibition features something for the whole family. In addition to the trains, the rooms of the historic Horace Greeley House will be festively decorated for the season, with several full-sized holiday trees decorated by local designers. For those who are young or young at heart, we offer a train-themed scavenger hunt, an activity room with crafts and hands-on trains, and even a mini train engine for the perfect photo op! Stop by our shop before you leave for the perfect holiday gift.

100 King Street Chappaqua, NY 10514
2025 Westchester Jingle Bell Run
13 Dec, 2025
Saturday
8:30 am
11:00 pm

2025 Westchester Jingle Bell Run

Please join us on Saturday December 13th from 9 am - noon at Manhattanville University for the annual Arthritis Foundation Jingle Bell Run, presented locally by Northwell Orthopedics! Timed & untimed 5K, entertainment, refreshments, vendors, kid's activities, Santa & Mrs. Claus, and other holiday festivities! Help support the 1 in 4 Westchester residents suffering from over 100 forms of arthritis.

2900 Purchase Street, Purchase, NY 10577
The Great Holiday Train Show!
13 Dec, 2025
Saturday
10:00 am
4:00 pm

The Great Holiday Train Show!

This beloved annual tradition returns to the New Castle Historical Society's Horace Greeley House for its fifth year. 2025 brings new featured layouts, including LEGO Around the World, alongside classic family favorites like the Polar Express and Santa’s Holiday Train. This unique holiday exhibition features something for the whole family. In addition to the trains, the rooms of the historic Horace Greeley House will be festively decorated for the season, with several full-sized holiday trees decorated by local designers. For those who are young or young at heart, we offer a train-themed scavenger hunt, an activity room with crafts and hands-on trains, and even a mini train engine for the perfect photo op! Stop by our shop before you leave for the perfect holiday gift.

100 King Street Chappaqua, NY 10514
Holiday Fineries at the Wineries on the Shawangunk Wine Trail
13 Dec, 2025
Saturday
11:00 am
5:00 pm

Holiday Fineries at the Wineries on the Shawangunk Wine Trail

Unwrap the magic of the Hudson Valley’s coziest holiday tradition. Three festive weekends: November 22-23, December 6-7, and December 13, 2025.  Time: 11:00 AM – 5:00 PM each day Celebrate the season one sip at a time! Savor holiday flavors, explore the beautiful Hudson Valley, and collect keepsakes that will make you smile for years to come. Holiday Fineries at the Wineries is one of the longest running holiday events of its kind, hosted by the member wineries and cideries of the Shawangunk Wine Trail! Full Experience Event Ticket are $45 (+tax/fees) per person and include:

  • (1) Shawangunk Wine Trail Tasting Glass. • (1) 2025 SWT Holiday Ornament. • (4) Wine tasting flights (1) at each location on your chosen itinerary. • (4) Winery Holiday Ornaments (1) from each location on your chosen itinerary.
Designated Driver Tickets are $15 per person (+tax/fees) and include:
  • (4) Non-alcoholic beverages (1) at each location on your chosen itinerary. • (1) 2025 SWT Holiday Ornament at the starting winery on your chosen itinerary. • Voucher for (1) FREE Wine Tasting Flight, redeemable on a future visit to any Shawangunk Wine Trail member winery. Choose Your Holiday Adventure: Select your date, starting winery, and one of three curated itineraries — each featuring four locations arranged for easy travel between stops.
Northern Itinerary #1
  • Robibero Winery, New Paltz
  • Whitecliff Vineyard, Gardiner
  • Christopher Jacobs Winery at Pennings Vineyard, Pine Bush
  • Angry Orchard Cider House, Walden
Central Itinerary #2
  • City Winery Hudson Valley, Montgomery
  • Magnanini Farm Winery, Wallkill
  • Quartz Rock Vineyard, Marlboro
  • Benmarl Winery, Marlboro
Southern Itinerary #3
  • Brotherhood, America’s Oldest Winery, Washingtonville
  • Applewood Winery, Warwick
  • Clearview Vineyard, Warwick
  • Warwick Valley Winery & Distillery, Warwick
From twinkling lights to the clink of glasses, our wineries will be decked out in festive décor and pouring seasonal wine and cider flights to put you in the holiday spirit. Celebrate over three festive weekends filled with tastings, keepsakes, and scenic holiday charm. Tickets are on sale now. This event sells out year after year, so don’t wait to get your tickets. For tickets, an itinerary map, and event details visit https://www.shawangunkwinetrail.com/holiday-fineries-at-the-wineries/

12 Multiple Locations in Orange and Ulster Counties Hudson Valley
Comedy From Scratch at The Idea Kitchen Larchmont “Best of Westchester Comedy Show” – BYOB Stand-Up with Katie Hannigan
13 Dec, 2025
Saturday
8:00 pm
9:30 pm

Comedy From Scratch at The Idea Kitchen Larchmont “Best of Westchester Comedy Show” – BYOB Stand-Up with Katie Hannigan

Comedy From Scratch is where you go in Westchester County to hear top comics from TV and NYC's major clubs performing long sets on an intimate stage. Past performers include comedians from HBO, Netlfix, Colbert, SNL, the Daily Show, Letterman, the Tonight Show, Comedy Central, and more. Every month, Ben Asher's presents comedy that reaches up into your brain with the force of a fist through the nose. Named "Best Comedy Show in Westchester" by Westchester Magazine. Every month you can hear some of the most talented comics perform long sets, that other shows don't give them the time to perform. Comedy From Scratch is your chance to get to really watch comedians flex their muscles and hit their stride on stage, at The Idea Kitchen. Locally-grown comedian Ben Asher presents a tasting of what the area's best stand-up comics are cooking up, at 'Comedy From Scratch' at the Idea Kitchen every 2nd and 4th Saturday of the month - that's right, you demanded more comedy, so we now give Westchester Comedy Twice a Month! Tickets available at https://ComedyFromScratch.eventbrite.com Show at 8:00 PM. Seating at 7:00 PM (bring your food and drink/wine with you and sit down at our tables to eat before the show and pick out your seats!!) Admission is $25 in advance, and $30 if purchased the day of the show. (Unlike Comedy Clubs, There is NO 2-Drink Minimum at this show)(and there is Free Parking.) BYOB and your own food/snacks/pizza (Half-Time and Sal's Pizza in Mamaroneck, or Nicky's Pizza in Larchmont is recommended!) Updates to line-ups may be posted the week of the show here or you can follow @the_ben_asher on Instagram (line-ups are subject to change, but rarely, and will always be amazing!) The December 13th lineup features: Katie Hannigan (Late Show with Stephen Colbert, HBO, Comedy Central) - https://www.katiehannigan.com Katie Hannigan is a stand up comic, actor and writer. Her stand up has been featured on The Late Show with Stephen Colbert, Comedy Central, Just For Laughs New Faces, The Late Late Show with James Cordon, and MTV. Her debut album Feeling of Emptiness was named Ten Best of 2022 by the Interrobang. Katie is a member of SAG AFTRA and has appeared in That Damn Michael Che, Succession, PBS Kids, commercials for Subway, Cheezits, Mabelline, Home Depot, and many indie films and sketches. Katie's writing credits include the original series Death Hacks staring Thomas Middleditch and Kristen Schaal, for Augenblick Studios. Katie hosts the popular podcast Lady Journey with comedian Sarah Tollemache. Ron Nobles (NY Comedy Festival) - https://www.ronnoblescomedy.com Ron Nobles is a New York City–based stand-up comedian known for his sharp storytelling and clean-cut, everyman charm. A staple of the NYC comedy scene, Ron performs regularly at clubs, colleges, and theaters across the country. He has been featured in the New York Comedy Festival and has toured across Europe, bringing his unique brand of humor to international audiences. Ron’s debut album, Trailer in the Sky, hit #1 on Spotify’s comedy charts and is now available on all major platforms. Produced/Hosted by BEN ASHER (New York Comedy Festival; StandUp NBC; Iceland Comedy Festival headliner; Caroline's; Catch A Rising Star; DoublePlusGood Comedy) - http://www.benasher.net Ben Asher, a writer and comedian from New York, is known for his “brave,” confrontational material, and his skills as a “brilliant joke writer” among fellow comedians. He performs regularly at comedy venues and colleges throughout the metropolitan area, East Coast, and Europe. Audiences are always quick to share their appreciation of Ben’s style of sardonic irreverence and absurd, satiric wit in which he doesn’t just dissect language and taboos - he explodes them. “What Ben Asher says makes me laugh, even though I feel like I shouldn’t." In 2022 Ben recorded a half-hour special "An Intimate Evening of Provocative and Deranged Humor" at The Nest rock club, in Brooklyn, NY. In 2024, Ben recently opened for Greg Fitzsimmons. Also, in 2022, Ben's show Arthur Avenue Comedy was featured in the NY Comedy Festival as one of only two comedy shows in Bronx. In 2014, Ben traveled to Iceland to headline in the Iceland Comedy Festival. He was also the finalist in the 2014 Funniest Jewish Comedian Competition. In 2013 Ben was in the New York Comedy Festival. Ben has been a guest on Sherrod Small's 'Races Wars' podcast. Ben currently produces and hosts the weekly Arthur Avenue Comedy show in NYC's Bronx borough, the monthly Comedy From Scratch at The Idea Kitchen, which was named “Best Comedy Show” by Westchester Magazine, and Slide-In at Slate-Nightclub in Manhattan's Chelsea neighborhood, and has produced and hosts a monthly comedy show in Park Slope, Brooklyn and New York's East Village, DoublePlusGood Comedy, (formerly Nasal Vice! Stand-Up,) where, since 2013, rising comics perform long, 20+ minutes sets, every month. He also co-produces/hosts The Homebrewed Mic, giving New Yorkers a sample of homebrewed beers and comedy. From TimeOut NY: For comedy connoisseurs tired of seeing their favorite comics squeeze their sets into five minutes, Ben Asher's showcase provides full-length sets and a chill atmosphere for diverse acts to thrive in. Press: In addition to being a TimeOut New York 'Critics Pick', TimeOut NY has frequently called Ben's show the "best cheap things to do," of the week and one of the “most amazing things to do” of the month, and the New York Times has listed it show as an editor's choice multiple times. Presented by The Stand-up Westchester Comedy Club - https://StandupWestchester.com QUESTIONS: Is This Venue Handicapped Accessible? YES. And please let us know how we can help you if you need any assistance. What Age is Appropriate For This Comedy Show? Should I Bring My Children? The material comedians discuss may be what you consider 'Adult' material. Anyone under 16 years of age should be accopanied by a parent or guardian. We would discourage you from bringing any child under 11 years old. If you child is age 11-15, and loves dark stand-up comedy (think George Carlin or Sarah Silverman) and you do, too, then we don't have any problem with them coming. However, if you child's only exposure to comedy is watching Seinfeld, Friends, or any situation comedy from TV, please do not assume you will be comfortable with material being discussed. Comedians on the show may discuss ANY aspect of human existence, or non-existence, in the darkest, most absurd way possible More show info available at: https://www.instagram.com/the_ben_asher o r https://www.facebook.com/BenAsherComedy or http://www.benasher.net You can always find out about upcoming "Best of Westchester" wining shows on The Stand-Up Westchester Comedy Club website by going to StandUpWestchester.com . What can you seriously expect? Just look which comics are frequently on my shows. This show is no BS. Past performers on Ben Asher's shows include comedians and writers from Saturday Night Live, the Tonight Show, the Late Show with Stephen Colbert, the Daily Show, HBO, Netflix, including: Ophira Eisenberg (NPR's Ask Me Another), Mark Normand (Comedy Central 1-Hour Special), Phoebe Robinson (HBO, 2 Dope Queens), Myq Kaplan (Netflix Special, Comedy Central Presents, Conan, Tonight Show), Mike Lawrence (Comedy Central Half-Hour, Roast Wars champ), Emmy Blotnick (writer Colbert, Comedy Central The President Show), Sam Morril (Comedy Central 1-Hour Special, Colbert, special ‘Up On The Roof’), Liz Miele (Comedy Central's "Live at Gotham"; Caroline's), Erik Bergstrom (Comedy Central Half-Hour, Colbert), Matteo Lane (Netflix, Late Nite w/ Seth Meyers, Comedy Central Half-Hour), Mike Recine (Conan; Comedy Central Half-Hour), Jena Friedman (The Daily Show, Conan, Adult Swim), Jacqueline Novak (‘Get On Your Knees’ off-Broadway hit produced by Mike Birbiglia, Comedy Central Half-Hour, The Late Late Show), Ben Kronberg (Last Comic Standing, Comedy Central Half-Hour), Vlad Caamano (Jimmy Kimmel Live, HBO, Comedy Central), Nick Vatterott (HBO's Real Time with Bill Maher, Comedy Central Half-Hour), Langston Kerman (Comedy Central Half-Hour), Josh Gondelman (Desus & Mero on Showtime; Jon Oliver HBO), Mehran Khaghani (TruTV, MTV, Comedy Central), Harrison Greenbaum (Conan, AGT, Comedy Cellar), Seaton Smith (Conan, Comedy Central, The John Mulaney Show on FOX), Tony Deyo (Conan, Letterman), Jon Fisch (Colbert, Letterman, The Tonight Show), Mike Vecchione (Comedy Central Presents half-hour special, the Tonight Show), Jordan Carlos (HBO, writer Colbert Report; The Gods Honest Truth), Beth Stelling (Netflix, Conan, Comedy Central Half-Hour), Aparna Nacherla (Netflix 'Master of None', HBO, Comedy Central Half-Hour), Jamie Lee (Ted Lasso, HBO's Crashing, Conan), Matt Koff (The Daily Show), Alingon Mitra (Conan; Last Comic Standing), Khalid Rahmaan (Conan; Comedy Central), Charles McBee (head writer The Gods Honest Truth Comedy Central, MTV)

1940 Palmer Avenue, Larchmont, NY 10538
The Great Holiday Train Show!
14 Dec, 2025
Sunday
10:00 am
4:00 pm

The Great Holiday Train Show!

This beloved annual tradition returns to the New Castle Historical Society's Horace Greeley House for its fifth year. 2025 brings new featured layouts, including LEGO Around the World, alongside classic family favorites like the Polar Express and Santa’s Holiday Train. This unique holiday exhibition features something for the whole family. In addition to the trains, the rooms of the historic Horace Greeley House will be festively decorated for the season, with several full-sized holiday trees decorated by local designers. For those who are young or young at heart, we offer a train-themed scavenger hunt, an activity room with crafts and hands-on trains, and even a mini train engine for the perfect photo op! Stop by our shop before you leave for the perfect holiday gift.

100 King Street Chappaqua, NY 10514
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