"...just a smile away from Whoville with a hint of It's a Wonderful Life."
—Huffington Post
Sinterklaas Send-Off Celebration, Kingston, New York
Sinterklaas Festival Day, Rhinebeck, New York

Sinterklaas Festival Day in RHINEBECK



Saturday December 1, 2018, Rhinebeck, New York

A day-long, colorful celebration that features children’s workshops, dance, theatre and music all over the village of Rhinebeck. Don’t miss the Dancing Bear, the Pocket Lady, and Mother Holly. The spectacular Children’s Starlight Parade at 6:00 pm, featuring two-story tall, animated puppets carried by hundreds of volunteers, closes the day at twilight. A non-denominational event, Sinterklaas joins residents and visitors alike, people of all ages and backgrounds, in a memorable celebration of children, art, and the light of the winter season.

View the 2017 program booklet online!


2017 Sinterklaas Rhinebeck Schedule

(Scroll to the bottom of the page for a handy MAP)

BEGIN your Sinterklaas Day . . .

10:00am BEAR BEAUTY CONTEST at Samuel’s
Dress your favorite bear up in anything you wish, meet other bears, and maybe win a prize. All children and adults are invited to submit entries! 
Many categories! Many honors!


Fire House 76 E Market St
Children are at the heart of the Sinterklaas story: They are KINGS & QUEENS of the Day and we honor them in the Parade and the Pageant. Make sure they get a chance to make their crowns and adorn their branches for the evening events!

  • CHILDREN Before you leave the workshop be SURE to visit the Wish Lady: Make your wish for your family, your community and the world. Tie them in your branch.
  • ADULTS be sure to place Your wishes in the Peace Dove!
  • PARENTS purchase your STARS so you can participate in the Children’s Star Celebration following the Parade.

Opening Ceremony

at the Beekman Arms, 6387 Mill St (Rt 9)
with jesters, puppets & stories — fit for our Kings & Queens! Be sure to get your Elephant Mask when you arrive.

  • Words Before All Else with Jeanne Fleming, Creator of Sinterklass with the Mother of All Mastodons, African and Indian Elephant Dancers and Musicians, the Pocket Lady, the Polar Bear, the Pachyderm Palace Model and a BIG SURPRISE!
  • Let’s Rumble with Reggie Harris and Betty and the Baby Boomers
  • STORYTELLING by famed storyteller Jonathan Kruk. Hear the legend of St. Nicholas and Dutch New York, Hanukkah Stories, and Elephant Tales.



The Bindlestiff Family Cirkus presents

Foster’s Parking, center of town.

  • Comic Daredevil Michael Rosman (look for showtimes posted in the lot)
  • The Home Spun Merry-Go-Round

Visit the Pachyderm Palace Theater

The Courtyard, off E. Market St.
Step inside the Giant Elephant and be treated to his Shadow Puppet Dream!! Created especially for Sinterklaas by artists Paul O’Connor and Liz Howls

Afternoon flights of fancy with the Bindlestiff Family Cirkus

at Upstate Films, 6415 Montgomery St perfect for ages 3 and up

  • 1:00pm, 2:00pm, 3:00pm — Bindlestiff’s Sinter Cirkus Starring Ringmistress Philomena & Mr.Pennygaff.
  • 1:30pm, 2:30pm, 3:30pm — Paris, the Hip Hop Juggler Interactive stunts, witty comedy, and world class juggling.

Plus… in-between show entertainment with Brandon Shih’s Kong Zhu YoYo Fun!!

Toy Theater

Methodist Church Parish Hall, 83 E Market St (next to the Church)
4 Big TINY Puppet SHOWS with Continual performances

  • Punch & Judy Show
  • Liz Joyce & A Couple of Puppets: Goldilocks & the Three Bears
  • Hao Bang-ah, Rooster! Chinese Hand Puppet Show
  • Jonathan Kruk Storyteller
  • The Blind Men and the Elephant with Liz Howls


The Beekman Arms, 6387 Mill St (Rt 9)
Hosted by the unforgettable Mrs. Beekman (our own Cindy Kubick)

  • 1:30 — Leela Puppet Theater A Boisterous Rajasthani Marionette Circus
  • 2:00 — Roger the Jester Mad Cap Fun!
  • 2:30 — Dog on Fleas
  • 3:00 — Tom Hanford Puppets Wassail, Wassail! Songs and Stories of the Season
  • 3:30 — Funkrust Brass Band
  • 4:00 — Hungry March Band
  • 4:30 — Leela Puppet Theater

Visit the ILLUMINATED BOOK On display in the Beekman Arms. Created by Nadine Robbins, Grace Gunning, and Molly Ahearn with help from James Gurney, Richard Prouse, and Andy Neal.

SinterFeature Jay Ungar & Molly Mason Family Band

New This Year at the United Methodist Church, 83 E Market St (across from Town Hall)

  • 2:00pm — Jay Ungar & Molly Mason Family Band
  • 2:30pm — Mamma’s Marmalade
  • 3:00pm — Jay Ungar & Molly Mason Family Band
  • 3:30pm — Gospel & Folk with Reggie Harris and Betty and the Baby Boomers
  • 4:00pm — Jay Ungar & Molly Mason Family Band

Music, Dance & Theater

Church of the Messiah, 6436 Montgomery St

1:00pm — Orchestra Now Chamber Players

2:00pm, 3:00pm, 4:00pm
Into The Light: A Holiday Spectacular

Presented by The Vanaver Caravan & The Arm of the Sea Theater. A Holiday story of a Young Girl’s Journey throughout the World searching for the Light. Features Giant Puppets and international music and dance!

Music & Magic

The Third EvangelicaL Lutheran Church, 31 Livingston St.

  • 2:00 — Caprice Rouge Balkan & Klezmer
  • 2:30 — Bard College Georgian Choir
  • 3:00 — BaseStation68 School of Jazz
  • 3:30 — Grumpus Magic by Andy Weintraub
  • 4:00 — Raspberry Hill Fiddlers

StoryTelling in MUSIC

Reformed Church Sanctuary, corner of South St. & Route 9

  • 2:00 — Funkrust Brass Band
  • 2:30 — Souls United Interfaith Gospel Choir
  • 3:00 — Key of Q LGBTQ & Allied a cappella singers
  • 3:30 — Vassar Devils a cappella<

Music & Dance

Town Hall, 76 E Market St

  • 2:00 — Mid-Hudson Mexican Folkloric Group
  • 2:30 — Hungry March Band
  • 3:00 — T McCann Band
  • 3:30 — Giglio Italian Band
  • 4:00 — Solas An Lae, Irish Dance

Music at the Bar

Liberty Public House, 6417 Montgomery St

  • 2:00 — T McCann Band, Irish Music
  • 3:00 — Caprice Rouge, Eastern European Music


HOT MEALS! Fun food all over town.
Visit Our Local Restaurateurs. And the Churches are serving :

  • 11:30-4:30pm — Third Evangelical Lutheran Church
  • 11:00am–5:00pm — Church of the Messiah Parish Hall
  • 3:00–8:00pm — Reformed Church Spaghetti Dinner

All Around Town Roaming the streets for your entertainment…

• Mother of All Mastodons with her Mouse. Receive Wisdom Words.
• Mother Holly
• Riddles with the Mad Hatter
• Batala New York Samba Band
• Hungry March Band
• Roger the Jester
• Pocahontas 1859 Hand Pump Fire Truck
• Pokingbrook Morris Dancers
• The Polar Bear with his trainer
• The Pocket Lady
• Grumpuses
• The Chinelos
• Elephant Dancers
• Bond Street Stilt Band

The Polar Bear with his Trainer & Musical Sidekick Sing a song & watch the bear transform.
The Pocket Lady Sinterklaas’ Symbol of Generosity. Find her with her “Pocket Lady Pal” just about anywhere around town. Go inside her beautiful cape and see what secret surprise she has in store just for you!
Mother Holly Become a member of the Eleophant Tribe. Hear stories of creatures large & small.
Our Own Grumpuses Dancing all around town.
The Chinelos Traditional dancers in spectacular costumes from the state of Morelos, Mexico.

Face Painting
All Afternoon at Iconic Hair! 7 W Market St

Abstraction Dutchess Day School Students’ Art Exhibit
Montgomery Row Art Exhibition Space Gallery, 2nd floor at 6422 Montgomery St (Route 9)

Living Nativity, Reformed Church

Havdalah Candle Lighting

In the Dapson-Chestney Parking Lot. Walk two blocks west from the traffic light. Led by the Northern Dutchess Hebrew School, J.A.N.D. and Temple Emanuel.

…and into the night

Children’s STARlight PARADE & Grand Final Pageant

Bring your Crowns & Branches, STARS & Flags!

Parade begins on West Market St. and proceeds through the Village & continues to the Municipal Lot for the Star Pageant. See the map below for the route.


6:30 pm
in the Municipal Parking Lot immediately following the Parade.
Join in at the end of the Parade to be a part of the Children’s Star Celebration featuring Fire Juggling, The Blessing of the Elephant, On the Lam Band, The Peace Dove.

7:30 Wassail From Liberty to Grand Cru.

7:30-9:00pm HoeDown in Town Hall Quickstep with John Kirk, Trish Miller & Ed Lowman. Great for Families!

8:00 pm
More for the grown-ups!
Reading & Book Signing at Oblong Books, 6420 Montgomery St.
GREGORY MAGUIRE - HIDDENSEE: The Once and Future Nutcracker

Sinterklaas DANCE at Liberty For Adults.

With the Dixieland sound of the On The Lam Band and an explosion of sound with the Forefathers of Funk


*Please Note: The schedule may be modified subject to weather or unanticipated changes.