Family FunLocal EventsRelocation December 8, 2021

December Happenings of 2021

Here are some December Happenings version 2021! Yes, I am a bit late with this post and I do apologize about that! Since working with so many transplants from the city, many of whom are eager to get to know the area, I am bombarded with a plethora of questions on what to do up this way. They are seeking fun local activities, events, and such. So, I have decided to create monthly newsletter-type entries showcasing a few local fun things to do for the month.

December is underway, Christmas is almost here and Hanukkah just wrapped up for the year. I love the holidays, don’t you? The lights, the energy, the shopping, and the fun things to do! But being from the city, it’s not as simple as just a train ride or bumping into something interesting randomly while walking down the street. Up here, you’ll have to do some research or be a part of a great Facebook group in order to get an idea of what’s happening for the month. So to keep it a bit more simple for you, here are some great things to do this month with your family in tow or just solo.

December Happenings

Christmas in a small town

1 – Museum Village’s – Christmas in the Village – Monroe

From December 11th at 11 am to December 12th at 4 pm, experience Museum Village’s winter wonderland! Listen to carolers, shop local vendors, and meet Santa and Mrs. Claus.

2 – Sugar Loaf Holiday Celebration – Sugar Loaf

December 11th at 11 am, the Sugar Loaf Holiday Festival is extra-spirited this year. Guests will enjoy a festive day full of holiday cheer including:

  •  Hot cider courtesy of the Sugar Loaf Community Foundation;
  • Treeside caroling with the Warwick Valley Chorale, Warwick Valley High School Treble Choir, and the Warwick Valley High School Meistersingers;
  • Visits with Santa to share wishlists and capture keepsake photos;
  • Horse Drawn carriage rides through the village of Sugar Loaf (weather dependent) from 1-4:30pm;
  • Tree lighting at 4:30pm;
  • Shopping the dozens of artisan shops and boutiques
  • Dining and snacking at local village eateries.
  • Shopping Discount Ticket for all guests! Stop in White Rabbit Restorations at 62 Wood Road to pick up a ticket valid for shopping discounts and freebies from shops and eateries throughout the Village of Sugar Loaf.

Additional details and updates available at

3 – Breakfast With Santa! – Chester

December 19th at 7:30 am, Santa’s Firehouse Elves are hard at work cooking breakfast for you!

  • $10 per elf
  • $5 per seasoned elf (65+)
  • Free for tiny elves 4 and under

Santa clause's hand, reaching for a cookie

4 – Santa Paws – Pet photos with Santa – Tractor Supply Co. in Pine Bush

December 11th at 11 am, all pets and children are welcome to have their photos taken with Santa for just $10! They will also have a raffle table of goodies and Christmas gift ideas.

-Each photo will be printed out on site. The photos will also be posted on this page the week after the event.

5 – Breakfast with the Grinch – Home2 Suites by Hilton Middletown

Sunday, December 19th at 10 am – 12 pm, Visit Home2ville at the Home2 Suites Middletown on Sunday, December 19th from 10 am-12 pm! Enjoy breakfast with the Grinch, crafts, and face painting by Legends Barbershop!! Bring your cameras for lasting memories. Reservations are required. Please email: to reserve.

  • $20.00 for Adults & Children (in advance)
  • $25.00 at the door
  • Children under 1 are free

6 – Holiday Craft & Vendor Fair – Sloatsburg

December 11th from 10 am to 4 pm, shop this year at our special Holiday Library Holiday Craft & Vendor Fair, which sets up this season at the Sloatsburg Senior Center.

7 – Brunch with Santa – The Thayer Hotel at West Point

December 5th, 12th, and 19th starting at 10:30 am, join in for their award winning Sunday Champagne Brunch with special guest, Santa! View the Menu:

Reservations required.
10:30 AM, 11:00 AM & 1:30 PM
Call to make your reservation: 845-446-4731 ext. 7929

8 – Wynonna Judd – Sugar Loaf Performing Arts Center

Wednesday, December 15th, at 6 pm, Orange Motorsports & Entertainment is pleased to present WYNONNA JUDD with a special holiday show at the Sugar Loaf Performing Arts Center, in Chester, NY. Tickets · $60 – $75.

gold wrapped Christmas gift

9 – Holiday Artisan Fair – Mamakating Environmental Education Center

December 11th at 10 am to 3 pm, Enjoy a festive atmosphere as you peruse the wares of local artisans. Find unique gifts, enjoy holiday refreshments, and support local business at the same time.

10 – Santa at the Tap House – Pine Island Tap House

December 18th from 2 pm – 5 pm, guess who is coming to the Tap House??? You got it, Santa! Oh, what fun this is going to be!!!!

Santa will be here from 2 pm till 5 pm on Saturday, December 18th. Please stop by with your children or adults and say hi to Santa and take a picture and tell him what you want for Christmas!
This is a free event.

11 – Winterfest – Sloatsburg Train Station

December 12th, 12:00 PM – 5:00 PM, Save The Date – Chamber’s Annual Winterfest! Join in and enjoy decorations and holiday music, food & craft vendors, children’s crafts, warming stations, our Chili Contest (judging at 2pm), Ugly Sweater Contest (judging at 3pm). Contact Jessie at to register for the Chili contest. Contestants should bring chili croc pots by noon to the pavilion. Winner announced at 2:00pm. $5 to taste and vote for best chili. Good luck!
festive Christmas cookies

12 – Holiday Market – The Yard – Beacon

December 11th at 10 am, this market will feature 30+ Hudson Valley Artisans. There will be food vendors, live music, an airstream turned bar serving beverages (alcoholic + non-alcoholic), incredible artisans with SO MANY HOLIDAY GIFT IDEAS and so much more…

13 – Ugly Sweater Party – Hillcrest Entertainment Inc – Florida

December 11th at 8pm, Join in at Hillcrest Entertainment for an ugly sweater party! Come enjoy a night out where the food is always great and the drinks are always cold, all while wearing your ugliest sweater! Saturday. Please bring a New unwrapped toy to contribute to the Toys for Tots program to Make Christmas special for a Child who may otherwise not have one.

14 – Home At Last – the Brewery at Orange County Hops – Walden

December 1oth at 5:30 pm to 7:30 pm, beer and music always makes for a good time! Performance by Tom Rausch Gigs.

15 – Holiday Boutique – Stony Point

December 12th from 9am to 3pm, the Holiday season is upon us. So get your shopping started by supporting local businesses at Powerhouse Dance Center’s Holiday Boutique.

cup of hot cocoa with whip cream on top

16 – A Christmas Carol – Dinner Theatre Show – New Windsor

December 18th at 4:30pm, You’ve seen Scrooge, Tiny Tim and the Ghosts of Christmas from a theatre seat. This season, why not dine with them?

17 – Westchester’s Winter Wonderland Drive-thru Holiday Light Extravaganza – Kensico Dam Plaza

Holiday season from 6pm to 9pm, Westchester’s Winter Wonderland Drive-Thru Holiday Light Extravaganza, presented by Westchester Medical Center Health Network, returns to Kensico Dam Plaza bigger and better than ever with thousands of more lights, magical holiday animations and a live Santa!

boy playing in snow

18 – Kids New Years Bash – Newburgh Mall

December 29th, at 1 pm to 3 pm. First… Live Magic Show with The Great Charlini. Afterwards celebrate the New Years with the countdown and the ball drop. Then… race painting and fun with Ms. Bubbles and Pals. Snacks and bottle of water will be provided (please note that snacks may not be allergy-friendly).

19 – Holiday Lights on Jenkins Court – Ossining

Reoccurring until January 6th 4:30-9:00 pm. Lights on Jenkins Court is the Staples family’s home light show. The show has run each year since 2017 during the holiday season. Jeff started designing and programming holiday light shows as a hobby over 6 years ago. Today, hundreds of Ossining residents stop by the house to see the 23 minute light show.You can watch the show at 12 Jenkins Court, Ossining. Tune to FM 90.5 to hear the medleys that accompany the display of lights.

Enjoy the holidays and check out some of these December Happenings! As I stated at the beginning of this post, this is only some of what’s going on in the area but it’s plenty to keep you busy! And if you’re looking to migrate up this way, looking to buy or sell in the Hudson Valley area, contact me! I’d love to help!