Check out our NEW Winter Activities and Events List! - Westport Moms

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 [email protected] 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.

Stay close to home!

Light Shows

Meet Santa!

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.

And more!

  • Candy House Workshop at the Fairfield Museum and History Center – Saturday, December 9th from 10am – 130pm. Holiday fun for the whole family. Celebrate the magic of the season by creating a sweet and colorful Candy House. Let your imagination bring to life a holiday scene decorated with gumdrops, peppermints, marshmallows, licorice and delicious treats! Members: $10; Non-Members: $15 per house. Register HERE!
  • Van Gogh Immersive Experience Step into Van Gogh’s Paintings with the help of 60,600 frames of video, 90,000,000 pixels, and 500,000+ cubic feet of projections, this captivating digital art exhibit merges state-of-the-art technology, theatrical storytelling, and world-class animation.
  • Disney’s Frozen on Ice – January 4th-7th, 2018 at Bridgeport Webster Bank Arena – Discover the full story of Disney’s Frozen like never before at Disney On Ice presents Frozen! Dazzling ice skating, special effects and unforgettable music will magically transport you to wintry Arendelle. TICKETS ON SALE NOW!
  • Family Festivities Musicals at The Westport County Playhouse – Don’t miss the incredible Family Festivities Musicals at the Westport Playhouse, kicking off with A Christmas Carol on December 17th, and culminating with Harry the Dirty Dog on May 6th! All shows are on Sundays, run 1 hour in length, and have a 1pm and 4pm show. TICKETS ON SALE NOW!
  • Greenwich Reindeer Festival – November 24th – December 23rd – For the 9th year, the Reindeer Festival kicks off on November 24th and continues through December 23rd. It takes place at Sam Bridge Nursery & Greenhouses, 437 North Street in Greenwich. Visit LIVE REINDEER and take photos with Santa! There are also train & Carousel Rides! Photo, Train, and Carousel Houses: Monday-Friday – 12noon-6pm and Saturday – 9am-6pm
  • Marvel Universe LIVE! Age of Heroes – March 1st – March 4th at Bridgeport Webster Bank Arena. Marvel fans, assemble! Marvel Universe LIVE! is an epic show unlike anything you’ve seen before. Watch your favorite Marvel Super Heroes including Spider-Man, The Avengers – Iron Man, Hulk, Black Widow, and more, and sinister villains come to life in a live, action-packed arena performance. TICKETS ON SALE NOW!
  • 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)– Friday December 2nd and Saturday, December 3rd
  • 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!
    • Charlie Brown Christmas – Saturday, 11/25 – 1pm and 4pm
    • Paw Patrol LIVE! – Tuesday, 12/5 at 6pm, and Wednesday, 12/6 at 10am and 6pm
    • The Nutcracker – Saturday, December 16th at 2pm and 6pm and Sunday, December 17th at 1pm and 5pm
    • Frozen Sing-a-long – Saturday, December 30th at 1230pm and 330pm
    • Underwater Bubble Show – Saturday, January 13th at 7pm


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