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Winter Activities & Events

With the winter upon us, we have put together some local activities and adventures, as well as when is best to book these. Please feel free to email us at info@westportmoms.com with any others we may have missed! For additional ideas of other great indoor activities during the cold, dark months, check out our Indoor/Rainy Day Activity List here and for any ski mountain or rental info, check out our All Things Skiing List here.

  • 11th Annual Greenwich Reindeer Festival & Santa’s Workshop – November 23rd to December 24th 2019, at Sam Bridge Nursey & Greenhouses in Greenwich. Come join us for holiday fun! Photos with Santa visit and feed Santa’s LIVE reindeer, contests, special offers and more. The festival kicks off on November 23rd with photos with Santa and other activities, and Santa’s reindeer arrive on November 29th.
  • 11th Greenwich Holiday Stroll Weekend – December 7th – December 8th, 2019 in Greenwich, Bryam, Glenville, Cos Cob, and Riverside. Shop, dine, and be merry with over 143 participating merchants. Visit us here for more information and scheduling.
  • 26th Annual Holiday Train Show – November 27th, 2019 – February 23rd, 2020 at the Connecticut River Museum. The family friendly Holiday Train Show exhibit is back at the Connecticut River Museum for its 26th year of fun for all ages. See what train artist Steve Cryan has created this year! A fully operational 26-foot train layout, “I SPY” scavenger hunts, and toddler sized viewing layout are all part of the fun!
  • Cirque Musica Presents Holiday Wishes – December 8, 2019 2 PM at the Webster Bank Arena. Cirque Musica presents Holiday Wishes brings a holiday story to life in a full theatrical cirque event for the entire family. Featuring the world-renowned cast of Cirque Musica with your favorite holiday hits all performed LIVE by a full symphony orchestra. Audiences will be amazed by the acrobats, aerialists, hilarious hijinks and holiday cheer. The show blends the spellbinding grace and daredevil athleticism of today’s greatest circus performers with the sensory majesty of a symphony orchestra.
  • Downtown Cabaret Theatre Holiday Shows – Taking the stage from November 16th to December 29th, tickets for Rudolph are on sale now! Everyone’s favorite reindeer is here to help Santa save Christmas! He may be a little different, but when a snowstorm threatens to cancel Santa’s annual flight, Rudolph with his nose so bright is the only one who can guide Santa’s sleigh tonight. It’s a classic Christmas tale about friendship, perseverance, and our differences making us special.
  • Family Festivities Musicals at The Westport County Playhouse – Don’t miss the incredible Family Festivities Musicals at the Westport Playhouse, kicking off with Peter Pan on December 8th, Judy Moody in January, Charlotte’s Web in February and culminating with The Pout-Pout Fish in March! All shows are on Sundays, run 1 hour in length, and have a 1pm and 4pm show. TICKETS ON SALE NOW!
  • Ice Skating:
    • Longshore Ice Rink (outdoor) – skate rentals (and sharpening) available for kids and adults; group lessons also offered. Ice rink opens on Friday, November 24th! 
    • Sportsplex Ice Rink (indoor) – year round lessons and skating available for kids and adults. Class sessions begin week of November 13th. 
  • North Pole Express at The Essex SteamTrain – Board the locomotive-powered sleigh for a magical nighttime journey to the North Pole. Every coach becomes a stage for a LIVE, musical performance of The Night Before Christmas. Celebrate the spirit of the season with Santa and Mrs. Claus, sing-a-longs, hot chocolate and sugar cookies. Each child will receive a small gift from Santa. Children are invited to wear their favorite PAJAMAS. Make sure those PJs are warm and cozy…it’s cold up at the North Pole! Ride length is approximately 90 minutes. TICKETS ON SALE AS OF SEPTEMBER!
  • Nutcracker Performance at Staples High School (performed by the Westport Academy of Dance)– Saturday, December 7th and Sunday, December 8th
  • Saugatuck Socials: Yule Stories – Thursday, December 19, 2019, 6:30 – 7:30pm at the Westport Museum for History and Culture. The Westport Museum of History and Culture began in Saugatuck in 1889. Members read interesting historical documents aloud or shared local stories. We invite you to join us on Thursday, Dec. 19, from 6:30 to 7:30 pm, to share stories, poems, historic essays and music with the rest of our community. Listen as others present original works or pre-selected pieces from history such as the Declaration of Independence or the Gettysburg Address.
  • Stamford Palace Theatre Winter Shows – Just 20 minutes away, The Stamford Palace Theatre has a wide range of options for kids and adults. There are some great holiday shows coming up you may not want to miss! TICKETS ON SALE NOW!
    • A Carpenters Christmas – Friday, 11/29 – 8PM
    • Twas the Night Before Christmas – Saturday, 11/30 at 1PM and 4 PM, and Wednesday, 12/6 at 10am and 6pm
    • A Christmas Carol – Friday, December 13th at 7:30pm
    • The Nutcracker – Saturday, December 21st at 2pm and 6pm, and Sunday, December 22nd 1pm & 5pm

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