With the holidays just around the corner, it’s hard not to be excited for the presents waiting for us to open under the tree this year. But the holiday season is much deeper than the things to open; instead, it’s the memories you make, the traditions you have, the people you spend time with that are most important. Here are some of my favorite traditions and activities to enjoy the holiday season, whether with friends or family!
Watch Christmas movies
There’s nothing like curling up with loved ones and watching Christmas movies to kick off the holiday spirit! Whether it’s timeless classics like “Rudolph the Red Nosed Reindeer”, animated favorites like “The Grinch”, or modern hits like “Home Alone” and a personal favorite, “Elf,” holiday films bring warmth and magic to any home. With cozy blankets, hot cocoa and a cozy fire, watching Christmas movies is the perfect way to create cherished memories, share laughter and enjoy the heartwarming stories that remind us of the season’s true meaning.
Build Gingerbread Houses
Another festive tradition that blends creativity, sweetness and a little bit of holiday magic, building gingerbread houses is a fun activity for all ages! Whether you bake the gingerbread pieces from scratch or use a pre-made kit, the process of constructing and decorating your very own gingerbread house brings everyone together. With colorful candies, frosting and icing, each house becomes a unique masterpiece. It’s a deliciously fun way to celebrate the season and a great opportunity to make lasting memories with family and friends while crafting a holiday centerpiece that’s almost too sweet to eat!
Ice Skate at Longshore
As the weather turns colder and snow is still a wish away, step into a true winter wonderland at Longshore in Westport, Connecticut. The rink offers the perfect atmosphere to enjoy the season’s chill—whether you’re skating laps or just soaking in the festive vibe. Don’t have skates? No worries, you can rent a pair! And if you’re new to the ice, skate mates are available to help you stay steady as you glide. Take a moment to watch the Zamboni work its magic, smoothing out the rink for another perfect glide. Afterward, warm up with a delicious cup of hot chocolate and a soft, giant pretzel, the perfect pairing to enjoy after a few spins on the ice.
Be sure to bundle up in a cozy jacket, gloves or mittens, and a hat or scarf—whatever makes you feel warm and ready to make the most of this classic winter experience at Longshore!
Caroling
Singing Christmas carols is a joyful tradition that fills the air with festive cheer and brings communities together. Whether you’re gathering with friends, family or neighbors, caroling spreads holiday spirit through timeless songs like “Jingle Bells,” “Silent Night” and “Deck the Halls.” Bundled up in cozy scarves and mittens, carolers make their way from house to house, spreading smiles and a little musical magic with each note. It’s a heartwarming way to share the joy of the season, create memories and remind everyone of the true spirit of Christmas.
Jones Family Tree Farm
A tradition of mine since I was born is visiting Jones Family Tree Farm. Located a short drive away in Shelton, Connecticut, this charming farm offers the perfect setting for selecting your own Christmas tree. Wander through rows of fragrant evergreens, handpick the perfect tree and enjoy the simple joy of cutting it down yourself. After, head down to their winery, where they have a holiday gift shop filled with decor and ornaments. Finish the outing off with their hot apple cider and a trail mix cookie. Whether you’re creating new traditions or continuing old ones, Jones Family Tree Farm provides a warm, welcoming experience that brings the holiday season to life.
Secret Santa
A holiday activity that brings a little mystery and a lot of joy, Secret Santa is all about giving and spreading festive cheer! In this fun gift exchange, participants draw names and secretly shop for a surprise gift for their designated person, keeping their identity hidden until the big reveal. Whether you’re exchanging small, thoughtful trinkets or fun, silly presents, the excitement of receiving a surprise from a secret giver adds extra sparkle to the season. Secret Santa is a heartwarming way to foster generosity and make everyone feel a little extra special during the holidays.
See the Rockfeller tree
Just a one-hour train ride from Westport, experiencing the magic of New York City’s Rockefeller Center during the holidays is an unforgettable tradition. The iconic Christmas tree, adorned with thousands of twinkling lights and crowned by a stunning Swarovski star, is a must-see. If you just want to soak in the holiday atmosphere, this outing offers a perfect blend of excitement, tradition and seasonal charm. It’s a short trip that delivers big holiday memories, making it a must-do for anyone looking to enjoy the best of Christmas in the city.
Decorate cookies
A beloved Christmas tradition for families and friends, decorating cookies is a festive way to get creative and indulge in sweet treats! Whether you’re rolling out dough from scratch or using a convenient Betty Crocker mix, the classic sugar cookie dough provides the perfect canvas for your holiday designs. With fun shaped cookie cutters, icing, sprinkles and candies, everyone can create their own edible masterpiece. Leave it out with a glass of milk for Santa!
