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Two’s Company Sample Sale
03 Dec, 2025
Wednesday
10:00 am
4:00 pm

Two’s Company Sample Sale

The Two’s Company Charity Warehouse Sale is a special, limited time event where the public can shop deeply discounted home decor, gifts and accessories from a brand that typically sells only to retailers. Held at the Two’s Company warehouse in Elmsford, shoppers can expect thousands of items at significant savings, with past events offering up to 90 percent off retail. A meaningful portion of proceeds supports local charitable organizations, making the sale both a community event and a way to give back. It’s a once a year chance for consumers to step inside the world of Two’s Company, discover great finds and support a good cause.

275 Clearbrook Road, Elmsford, New York
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
Holiday Fineries at the Wineries on the Shawangunk Wine Trail
06 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
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
Holiday Fineries at the Wineries on the Shawangunk Wine Trail
07 Dec, 2025
Sunday
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
The Irish Tenors
07 Dec, 2025
Sunday
7:00 pm
9:00 pm

The Irish Tenors

The Irish Tenors return to the Paramount Hudson Valley Theater on December 7 for an unforgettable evening of soaring vocals, heartfelt melodies, and timeless Irish charm, adding a wee bit of holiday music to enhance the festive spirit. Since joining voices in 1998, this beloved trio has captivated audiences around the world, performing to sold-out crowds at prestigious venues including Carnegie Hall, Radio City Music Hall, and the Sydney Opera House. Their legendary PBS specials, including the acclaimed Ellis Island, have reached millions and helped cement their status as the premier ambassadors of Irish song. Known for breathing new life into traditional Irish favorites, The Irish Tenors also surprise and delight audiences with contemporary classics and crossover hits. Their repertoire spans haunting ballads like “Danny Boy” and “Fields of Athenry” to interpretations of “My Heart Will Go On” and “Fairytale of New York,” all delivered with rich harmonies and emotional depth. This performance will feature the sweeping arrangements and vocal brilliance that have made their live concerts a must-see event. Joining Anthony Kearns and Ronan Tynan is award-winning Irish tenor Patrick Hyland. A native of County Kildare, Hyland has performed globally at esteemed venues including the Royal Albert Hall, Glyndebourne Opera House, and the National Concert Hall Dublin, and has earned critical praise from Opera News, Opera Today, and Opera Magazine. His powerful vocals and international operatic experience add a new dimension to the trio’s sound. Don’t miss this extraordinary night of music that celebrates Irish heritage and showcases the enduring power of the tenor voice. *As a reminder, no outside food or drink permitted in the venue. Any patron found with outside alcohol, is subject to removal. Backpacks and large bags are not permitted inside of the venue. All guests are subject to bag checks and security wanding upon entry. Event & ticket link: https://paramounthudsonvalley.com/events/the-irish-tenors/

One year in the books
12 Dec, 2025
Friday
10:00 am
5:30 pm

One year in the books

Celebrate Bedford Books’ first anniversary with a day full of gratitude and fun. Enjoy raffles, giveaways, special author visits, festive treats, drinks, and free holiday gift wrapping. A warm thank-you event for the community that helped make this independent bookstore a beloved local hub.

13 Court Rd, Bedford, NY 10506
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