Southeastern Connecticut’s Winter Activities

There are so many activities to do in Southeastern Connecticut this winter. No matter which town you live in or which holidays you celebrate, ring in the season with fun festivities over the next few months!


What is Christmas without seeing Santa’s Arrival?! On Saturday, November 25, Santa visits Sherman Green from 10am to 2pm. Along with visiting with Santa and telling him what’s on your holiday wish list, there will also be a petting zoo, wagon rides, hot chocolate and food for sale, face painting, and so much more!

If singing is more your thing, bring your family to the Frozen Sing-Along at the Fairfield Theatre on Saturday, November 25 at 1pm. The Fairfield Theater is also hosting more holiday shows, including A Broadway Holiday Show and Aaron Neville Christmas, both on December 17.

For the interior designer, architect, or lover of all things home design, a tour of the decorated Burr Mansion is the perfect treat. From November 30 to December 3, enjoy a cup of cider and meander through the beautifully renovated mansion for a holiday showcase called the Fairfield Christmas Tree Festival. Wreaths, trees and home decor will be for sale as well. Santa will also make an appearance so bring your kiddos!

On Friday, December 1, bring your friends and family to enjoy the Christmas Tree Lighting at the Town Hall Green. Choirs from Fairfield Woods, Roger Ludlowe, Tomlinson Middle Schools will kick off the event at 5:55 pm with the Fairfield Warde Choir singing at 6:20 pm. The Downtown Theatre Company will finish off the musical entertainment at 6:45 pm. The lighting of the tree will begin at 7 pm with Santa joining the group shortly after.

From December 1 to January 7, the Fairfield Museum will host their 11th Annual Holiday Express Train Show, a magical experience for kids to watch trains wind around a winter wonderland. The perfect activity for a child who loves model trains!

For the kids who can’t wait to give Santa their Christmas wishlist, they can drop off their letters in Santa’s Mailbox at the Parks and Recreation Department. Make sure to include your return address so Santa can write you back!

Bring your skates and toboggans to one of many sledding hills and ice rinks in Fairfield; sledding hills include Gould Manor Park, Sturges Park, Tunxis Hill Park, and outdoor ice skating rinks include Gould Manor Park and Owen Fish Pond.


A Christmas Carol – the quintessential holiday story. See this magical musical live at the Westport County Playhouse on Sunday, December 17 at 1pm and 4pm.

After you’ve got your Scrooge and Tiny Tim fix, stop by the Connecticut Audubon Society’s H. Smith Richardson tree farm to cut down a Christmas tree!


Four Norwalk attractions are hosting plenty of events this season. Kick off the season right by watching The Nutcracker at the Wall Street Theater on December 2, put on by Norwalk’s Metropolitan Youth Ballet.

Starting on November 24 and running on select dates through December 22, the Maritime Aquarium’s IMAX theater will be showing The Polar Express, one of our favorite holiday feel-good movies!

Before or after the movie, check out a shark-diving Santa at the aquarium! Santa’s exchanging his snow boots for fins as he dives into shark-invested waters at the aquarium, demonstrating that sharks don’t see humans as prey.

Our favorite grocery store, Stew Leonard’s, is hosting a slew of activities this winter. Check out their events calendar for events including Christmas Tree Lighting and Menorah Lightings. Their Newington location is hosting fun activities as well!

The Stepping Stones Museum is hosting events from Elf Workshops, Winter Workshops and Santa and Friends. Perfect for kids of all ages, check out the events calendar for specific dates and times throughout November and December. The museum will also be hosting Festivals of Light traditions from all over the world, including Kwanzaa, Hanukkah, Las Posadas and the Winter Solstice, every Sunday from December 3 until Christmas Eve.


What’s Christmas without having a beautiful, live tree to cut down? Maple Row Farm in Easton is open daily starting on November 24 and has everything from balsam firs to blue spruces.


If you live closer to Shelton, visit Jones Family Farm for their Christmas Trees. After the tree cutting, we suggest taking a trip through the gift shop to get wreaths, garland, tree stands and more, and end the day with a visit to their winery for a wine tasting.


Our favorite local zoo is hosting Breakfast with Frosty on December 9, 10, 16, 17 and 23 from 9-10 am. After breakfast, enjoy a walk through the zoo.

Webster Bank Arena will be hosting two festive shows: Cirque de Soleil Musica Holiday on December 12 and Disney on Ice’s Frozen from January 4 -7 so you can stay in the holiday spirit even after the New Year.

New Haven

New Haven’s annual Fantasy of Lights kicks off on Friday, November 17 and runs until December 31. Drive through Lighthouse Point Park as over 10,000 light bulbs light up the night sky! All proceeds from this special event will benefit the programs of Goodwill of Southern New England.


The Essex Steam Train is a staple of Connecticut. They’re hosting a slew of holiday activities throughout November and December, including a Reindeer Breakfast, Santa Special and the famous North Pole Express, where the train will travel to the North Pole! But make sure you book your tickets as soon as possible as most of the holiday trains have already been booked.


A Charlie Brown Christmas, another holiday staple, will be having a live-action stage adaption on Saturday, November 25 at 1pm and 4pm at the Palace Theatre. Join Charlie Brown, Snoopy, and the whole Peanuts gang as they light up the stage with their holiday antics.

If you find yourself in Stamford on December 3, check out Heights & Lights. Cheer for Santa, the Grinch, Rudolph and more as they descend 22 stories from Landmark Square. Then follow them to Latham Park for holiday music and tree lighting. This is sure to be a delight for kids of all ages!

Bring your tiny dancers to Chelsea Piers on December 9 for the Nutcracker Suites, a ballet show for young children put on by dancers from the Ballet School of Stamford.

Have a wonderful holiday season!

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Shoshana Snyder

Shoshana Snyder

Sarah Pritchard

Sarah Pritchard

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