Holiday Traditions: A Celebration of Creativity, Connection, and Joy
Discover heartfelt holiday traditions and creative inspiration from my friends and fellow artists, designers, and tastemakers who make the season bright.
As the holiday season approaches, I’ve been reflecting on the traditions that make this time of year so meaningful: the familiar recipes, decorations, and rituals we look forward to each year. Whether it’s baking a family favorite, decorating the house, or simply pausing for a moment of gratitude, these small acts connect us to one another and to our memories.
Traditions can be big or small, shared or unique. Sometimes we don’t even realize we’ve created one until it becomes something our families look forward to year after year.
This season, I wanted to spread a little joy, warmth, and inspiration by inviting some of my favorite creative friends to share the holiday traditions that mean the most to them. From Virginia to Texas, Illinois to New Jersey, and even across the Atlantic to England, we’re all connected by our love of community and meaningful moments.
Meet My Friends:
Jessica Williamson | JTW Design, Richmond, VA
Owner and Principal Designer
Website | Instagram
Let’s start here at home with a few local Richmond creatives. Jessica Williamson leads JTW Design, a luxury interior design firm known for creating fresh, timeless spaces. We met through a local networking group, and I’ve admired her ever since, not only for her design talent but also for the way she keeps her focus on what matters most: family and connection.
From Jessica:
Our church puts on an incredible service every Christmas Eve. It’s absolutely my favorite part of Christmas. It reconnects me back to the true meaning of why we’re celebrating in the first place. The service is music-filled, elegant, fun, and entertaining in a way that’s very meaningful. They end the service singing “O Holy Night” with a candlelighting. It brings me to tears every single year without fail.
Ever since our kids were little, my parents would spend the night with us after the service so that they could wake up with us on Christmas morning. Even though the kids are teens now, and my dad has since passed, we still keep this tradition alive.
On Christmas Eve, I prepare an elegant table with china, silver, and crystal. We always have a rack of lamb, scalloped potatoes, and a peppermint ganache pie that’s easy to make and completely decadent. See the recipe below!
Every Christmas morning, we have an easy and elevated brunch with casseroles, fresh fruit, and of course cinnamon buns.
On Christmas Eve, Jessica serves this super rich, no-bake pie with an Oreo crust and peppermint ganache filling.
Jessica and her team are also celebrating a milestone: moving into a brand-new office in Richmond’s Scott’s Addition neighborhood this December! Her hope for the season is to enjoy the process of packing up their office as a team, joyfully and without stress.
Theodora Miller | Theodora Miller, Richmond, VA
Artist and Textile Designer
Website | Instagram
Artist and founder Theodora Miller channels her Greek heritage and a warm, soulful spirit into everything she creates, from paintings and ceramics to textiles and wallpaper.
I’ve admired Theodora and her artwork for years and first met her in person when I happened to see her at a local school where I was planting seasonal containers. Her energy is infectious, and her work is as vibrant and genuine as she is. Her Greek heritage is a driving force in both her life and her art, and she has some wonderful New Year’s traditions to share with us.
From Theodora:
To jumpstart our New Year’s blessings, we embrace several Greek traditions in our family. The first is breaking a pomegranate, which is an ancient Greek holiday tradition with origins in the Peloponnese region, where my mother Athanasia and my grandparents Theodora and Constantinos were born. We believe that by smashing a pomegranate, we release its plentiful ruby-red seeds, thereby unleashing an abundance of health, happiness, and prosperity for the coming days, weeks, and months of the new year.
As soon as the clock strikes twelve (or whenever we return home from celebrating elsewhere), we throw down a pomegranate with force upon the front door threshold. Then, one by one, we step on the pomegranate and enter the home with our right foot, as a symbol of taking the right path forward in the year ahead.
A friendly tip for avoiding a mess: place your pomegranate inside a large or extra-large Ziploc bag, then double-bag it, but be sure to remove the extra air before sealing.
After a good sleep, we wake up on January 1st and get to baking, as it’s the Greek Orthodox Christian feast day of St. Basil, a 4th-century bishop. He is remembered for his compassion and his care for the poor. While there are many variations of how the Vasilopita came to be, my family has passed down the legend of him hiding the townspeople’s jewels and money from tax collectors by baking them inside a pita. The pita was then cut and distributed to each person, miraculously returning the jewels and coins to their rightful owners.
In honor of St. Basil, we bake a Vasilopita with a hidden coin inside. My late mother’s cake recipe includes fragrant orange zest and is baked in a round pan, topped with a generous heap of powdered sugar. The top is decorated with the numbers of the new year, usually made from nuts or edible silver beads. We cut the cake in a specific order, starting with a piece for God, the church, the head of the household, and continuing from the oldest to the youngest family member.
Just make sure not to inhale when taking your first bite, or you’ll have quite a mess (and a laugh)! The person who finds the coin in their piece of Vasilopita wins good luck for the entire new year, and the lucky coin is meant to be saved, because you should never throw away your good luck. We place it in a spot where it can be seen often as a friendly reminder of good fortune.
Theodora recently launched her debut line of wallpaper and fabric, aptly named the Ancestral Collection. I attended her launch party and was awestruck by the exquisite prints, all inspired by her heritage and her beautiful painting. The world is taking notice of her work in clay, too; her Blooming Girls vessel was on exhibit in the 1000 Vases exhibit during Paris Design Week this past September!
Vana Chupp | Vana Chupp Studio, Richmond, VA
Designer of Timeless 14K Custom Silhouette Jewelry
Website | Instagram
Vana Chupp Studio is a fine jewelry atelier dedicated to preserving life’s most meaningful stories into exquisite heirloom-quality jewelry. I met Vana when she co-created a local networking group here in Richmond, VA. She exudes elegance, peace, and style…and I make no apologies for staring at her stunning jewelry each time I see her.
Vana’s jewelry captures family stories in gold and silhouette, and her family’s own holiday tradition reflects that same spirit of connection and kindness.
From Vana:
The feast of Saint Nicholas, which falls on December 6th, honors the life and miracles of Saint Nicholas, the patron saint of children, sailors, and merchants. One of the most cherished traditions our family associates with the feast is the tradition of putting shoes under the Christmas tree.
According to history, Saint Nicholas would secretly visit houses during the night and leave gifts for children in their shoes. This tradition is a way to commemorate the saint's compassion and his dedication to helping those in need.
To this day, on the eve of Saint Nicholas' feast day, children place their shoes near the Christmas tree, eagerly awaiting the arrival of the saint. In the morning, they wake up to find their shoes filled with small gifts, candies, and sometimes even a small amount of money.
We cherish this tradition for several reasons. We began incorporating it when our oldest, Nikolas was just a toddler. It first began as a way to add an element of surprise and excitement to the holiday season while honoring the memory of a beloved saint whom our son was named after. We love the reminder of the importance of generosity and giving, encouraging each one of us to share our blessings with others. Through this tradition, we keep the spirit of Saint Nicholas alive, reminding us of his selflessness and inspiring us to follow in his footsteps.
This season, Vana is also celebrating the opening of her new showroom in Richmond, where local clients can schedule private appointments to design custom pieces or view her full collection in person. She loves the connections she’s built with local clients over the years. It's such a treat to help them imagine something new or assist them in putting to life a piece they've been dreaming up for years.
Tina Thomas — Tina Take My Photo, Richmond, VA
Branding Photographer and Video Creator, Emmy Award-Winning Marketing Producer
Website | Instagram
Aside from her photography and videography talents, Tina has an remarkable sense for business strategy and brand messaging, which make her a highly sought-after partner. Tina is a powerhouse of creativity, and her traditions beautifully blend family, food, and memories.
From Tina:
First, as a photographer, I always try to do a Holiday Photo Swap with a friend's family. We will use the Christmas tree area at either Cross Creek Nursery or The Great Big Greenhouse, which also has our favorite Santa! We've taken our son to see him every year.
Last year we created a new tradition for a simple night at home - a New Year’s Eve activity countdown! Every hour, I filled a paper bag with a treat or activity to help the kids stay awake and spend quality time together. Candy, games, food, etc. It was a big hit and he wants to do it this year as well! We decorated the bags earlier in the day for each hour, but he didn't know what was going into them. It was so much fun!
And of course we have a food tradition. We lost my mom last year, but she always made the most delicious, juicy, fragrant Christmas ham with cherries and pineapples that filled the room with the best smells. I plan to carry on that tradition with my family, too.
Tina is introducing Holiday Video Sessions this year, a fun new way for families or businesses to record personalized video greetings. They’ll have a special set in the studio and the final session will be offered on Nov 22.
Wendy Conklin | Chair Whimsy, Austin, TX
Artisan, Designer, Educator, and Entreprenista
Website | Instagram
Now let’s swing down south to Austin, Texas, home of Wendy Conklin — a former teacher turned chair stylist and entrepreneur. I first discovered Wendy on Instagram several years ago and later had the pleasure of learning from her in person at the first Pink Creatives entrepreneurial retreat she co-hosted in Round Top. She’s endlessly creative and radiates color, joy, and energy.
From Wendy:
Here is a recipe that I make every holiday season. It was my mom‘s coffee cake and it’s always a huge hit. But the kicker is it should be refrigerated in order to taste really good! And it’s amazing when it is. I use a fluted tube cake pan – I bake it, cool it to room temperature, then I wrap it in foil and put it in the refrigerator and serve it cold. It's so good in the mornings with your coffee and served cold. It really brings out the flavor and everyone loves it!
While you don’t have to refrigerate this cake, Wendy says it tastes so much better served cold!
Wendy always has something inspiring in the works, whether renovating their cabin in the Adirondacks, mixing fearless fabrics, or opening her joyful Texas home for tours. Watch for her new collection of prints, greeting cards, and tea towels, and her upcoming column in Cottages & Bungalows magazine in 2026.
JeriLynne Clifford | The Hill Country Bon Vivant, Fredericksburg, TX
Cookbook Author, Educator, and Entertaining Specialist
Website | Instagram
I also met JeriLynne at the Pink Creatives retreat and was instantly drawn to her warmth and generosity. Since then, we’ve stayed connected through our shared love of hosting and creating beautiful moments, including our Instagram Live series Planters & Parties. JeriLynne is thriving as a tastemaker and champion of the Texas Hill Country.
From JeriLynne:
Thanksgiving and Christmas are always celebrated with family and friends. On both holidays, we always have my dad’s stuffing, affectionately called “Papa’s Stuffing” by my children. The smell of sage, thyme, and rosemary means holiday to me. It doesn’t matter what protein that we are serving – we have to have it! Also on Thanksgiving, before we eat and after we’ve said the blessing, we go around the table and say one thing that we are thankful for this year.
JeriLynne’s new cookbook, The Vineyard Table: Cooking, Wine & Stories of Hospitality, is filled with recipes and heartfelt stories that celebrate grace, gratitude, and the joy of gathering. You’ll find “Papa’s Stuffing” on page 115. Spoiler alert, there are mushrooms and a hint of Bell’s Seasoning.
Howard Nemeroff | Plant Parenting, Chicago, IL
Container Gardening Designer
Next, let’s swing up to Chicago, where Howard Nemeroff has provided distinctive, award-winning container gardens across the city for nearly 40 years. I’ve been a fan of his since I first found him on Instagram (circa 2017?) and, even though we’ve never met in person, I consider him my friend. His work inspires me – and countless professional container gardeners across the country – every season, year after year.
From Howard:
One of my favorite holiday traditions is a decorative collaboration with Simply Flowers Design, a florist friend of more than 30 years. Together, we create a spectacular residential installation that includes a huge quantity of densely packed magnolia garland from Weston Farms out of North Carolina. A full truck of garland is shipped overnight to Chicago and picked up at the airport. We start creating immediately!
When you pour your heart and soul into your work, as Howard does, projects like this become a joyful highlight of your year, and perhaps even your career. Speaking of careers, in 2026, Howard will be celebrating 40 years in business. As always, he’ll be looking for interesting new plants and products to try. Happy 40th Business Birthday, Howard! Catch a glimpse of their magnolia installations from 2023 and 2024.
Howard is also deeply committed to giving back. He lends his talents to Designs 4 Dignity, an organization that transforms nonprofit spaces through design. “This organization speaks to me because it dovetails with a quote from the industrialist, Irwin Miller, who famously said, ‘mediocrity is expensive.’ What he meant by that was community investment pays big dividends.”
Another organization Howard would like to highlight, especially at this time of year, is The Greater Chicago Food Depository, which provides food for families in need.
Laura Boissonnault | How’s It Growing NJ, Woodbury, NJ
Life-long Organic Gardener, Shop Owner, Garden Designer
YouTube | Instagram
Heading back to the east coast, meet Laura Boissonnault, a Master Gardener in my childhood state of New Jersey. Her lifelong love of gardening began in childhood and continues to flourish today. One of her most cherished holiday traditions is making her mother’s sausage stuffing – a simple, comforting dish that instantly brings back memories of her family’s Thanksgiving gatherings. When I first found Laura on Instagram, I felt an immediate connection because of my Jersey roots and love of plants. Coincidentally, my family has a very similar dish to the one she shares that we call “Dad’s Secret Sausage Stuffing”, so the connection continues.
From Laura:
I’m sharing a recipe that my mom has made for my entire life and beyond. It’s her sausage stuffing recipe. Even though our family gatherings are smaller than they used to be, and I now host the dinner instead of my parents, the sausage stuffing remains. We always look forward to it, and the aroma instantly snaps me back to my childhood. The ingredients are readily available and anyone can make this. We measure with our hearts.
When it’s all cooked, I put some in a little dish and bring it to my parents who live 7 blocks away so they can taste test the day before Thanksgiving and make sure it tastes exactly like mom’s!
I’m so so thankful to have that close relationship with my parents, and my boys as well. I’m especially thankful this year to have my dad healthy after a heart procedure on Halloween. My husband, mom, and dad all have birthdays in November, too, so we have a lot to celebrate and be thankful for.
Laura’s Mom’s Sausage Stuffing
Bagged herbed stuffing cubes
Couple bunches of celery
Sweet onions
Salted butter
Botto’s sweet sausage, uncased (This is local to Laura in NJ. Use as little or as much as you’d like.)
Boxed chicken stock
Bell’s Seasoning
Start out with 2 large pans on the stove.
In one, I brown the sausage. No oil required, but you could do a little olive oil if you want. Break it up into crumbly bits as you cook.
While that’s going, in the other pan, I put 2 sticks of butter, plus lots of celery and onion in a rough chop so the celery stays a little crunchy.
Add salt, pepper, and a sprinkle of Bell’s.
Reduce it down to a nice soft, buttery goodness.
Now grab the biggest stock pot you can find (Laura’s was given to her by her mother; it’s so big she has to get on a stepstool to reach into it, making her feel like a kid again).
Start layering:
Cubed stuffing
Spoonful of sausage
Spoonful of celery and onion mix.
Keep layering, including all of the juices.
Then mix it all together. There’s a lot, so layering first helps you get it all incorporated. You want to make sure it’s not too dry, add chicken stock to make it more moist and yummy.
Reserve a tray of “stuffing” to go in the bird, and another tray of “dressing” to eat. My favorite is the stuffing cooked in the bird because it just tastes so good!
When they’re not cooking sausage stuffing, Laura and her husband are restoring a 1900s building in historic Woodbury, NJ. There, they plan to open The Garden Shop of Woodbury in 2026, featuring seasonal container designs, floral bunches, garden accessories, and more — a perfect extension of her passion for all things green and beautiful.
Caryl Tincknell | Violet Grey, Devon, England
Curator of Fine Garden Antiques
Heading across the Atlantic to Devon, England, meet Caryl Tincknell. She is the founder of Violet Grey, one of the UK’s most admired sources for garden antiques. Her curated collection of planters, furniture, and ornaments feels like a love letter to craftsmanship and history. One look at her Instagram feed and you’ll see what I mean.
From Caryl:
A special tradition at Christmas time in our house is largely based around homemade food. Christmas day is quite a small gathering: my 2 sons and wives, one great grandmother, a two year old grandson, and my husband!
I like to make all the usual Christmas food, including Christmas pudding, that is always flamed with brandy and is served with hot brandy sauce on Christmas Day after a huge roast Turkey and all the trimmings. The house is filled with twinkling fairy lights and decorated Christmas trees; it’s such a special time of year!
My specialty is sausage rolls and my family devours them! They have to be homemade and I can’t make enough of them! We usually see friends over the entire festive period. I make well over 200 sausage rolls and freeze them! They are given to anyone who comes over! There is never any left over!! The recipe is borrowed from a lady called Delia Smith, a well known TV cook back in the day,
You can view and print the recipe transcribed from Caryl’s cookbook, or find Delia’s Sausage Rolls here. Her story reminded me of how a single recipe can become part of a family’s identity. Food connects generations and brings comfort and joy to everyone who gathers around the table.
Our Tradition: Gingerbread Houses
One of my family’s favorite Christmas traditions is making gingerbread houses at my parents’ house. It started when the girls were little and has evolved into a full-on Gingerbread War with my mom, brother, aunt, friends, and now boyfriends all joining in. The competition is fierce — the kids (who are not so little anymore) plan their designs and gather specialty ingredients weeks in advance. My husband and I stay out of the fray until it’s time to deliver pizza and cast our votes for the winner. No pressure, but anyone who adds window boxes to their house gets my vote.😉
My mom still leads the charge with her teacher’s touch: the candy, frosting, and tools are organized on the table like a perfectly planned classroom project. My dad’s no longer with us, but he’s always here in spirit. He’s the one who nurtured the artist in me (and in our daughters), and we all still laugh remembering how he’d blanket his gingerbread house in confectioners’ sugar if it didn’t turn out quite right.
It’s messy, busy, and wonderfully creative — just the way the holidays should be.
A Season to Savor
I’m so grateful to these incredible creatives and tastemakers for sharing their stories and traditions. Reading their reflections reminds me how universal the spirit of the holidays truly is.
The simplest things — a cake chilled in the fridge, a child’s shoes under the tree, or the smell of something baking — can carry us back in time and help us celebrate what matters most.
Whether your traditions are long established or just beginning, I hope this inspires you to slow down, savor the season, and create moments that last.
Wishing you warmth, joy, and creativity this holiday season!
Steph
P.S. Share your favorite holiday tradition in the comments!