Photograph: © sewcream-stock.adobe.com

November means that the holidays are knocking on the door. With a little planning, parents can establish holiday traditions that children will cherish for a lifetime. Today, they may be in diapers but, trust us, in the blink of an eye they’ll be moving out and taking all the memories and traditions you have created. Here are a few ideas on how to celebrate the magic of the holidays through the generations.


Waiting for the big day to arrive can be exhausting for little ones, and as teens get older the holidays may lose a little of the magic. But with some planning in November, a homemade advent calendar can help keep the season festive. The personalization makes each day fun to open. The Historical Christmas Barn in Wilton (historicalchristmasbarn.com) is a great place to look for reuseable wooden Advent Calendars. Or if you’re feeling crafty, string together odd mittens, socks or felt bags and glue felt numbers 1 through 24 on each and hang over a mantel or an easy-to-reach doorway. Next, hunt for goodies. Go simple and inexpensive for most days, like a favorite candy or homemade cookie. About once a week, leave something a little more significant like an ornament, festive socks or “gift certificate” for a date to watch a favorite holiday TV show. I find that by counting down to Christmas, the little ones are less crazed when the big day arrives. As for the bigger ones, well, you just might get a smile out of them in the morning. It also inspires their own generosity as they start to think about what they can do to prepare.

This personalized approach is also great for the eight days of Hanukkah. Instead of being used as an advent calendar, it can be a celebration garland. Just choose socks, mittens or bags in shades of blue, white or silver, number one through eight and fill each night of Hanukkah. Also check out Chai & Home (chai-home.myshopify.com) for an array of unique countdown bags and an assortment of placemats and decorations.


A fun tradition to kick off the season is St. Nicholas Day, when St. Nick delivers small presents to good boys and girls. Growing up with German ancestry, my husband and his sister used to put a boot outside their door every December 5 and discover a few small treats the next morning. We have extended that tradition to our family. And even now that my kids are older, they prop an Ugg, Timberland or Wellie by their bedroom door and wake to find a few treats and an ornament.


I vividly remember my first post-college Christmas. When I unpacked my brand-new Kmart box of sparkly red balls, my roommate Lori opened up a well-worn shoebox filled with keepsake ornaments that her parents had given her every year since she was little. She filled our first single girls’ tree with a lifetime of cherished memories. I have since embraced this tradition, and now every December I buy a special ornament that represents something personal from the past year for my kids, nieces and nephews. They range from acknowledging special accomplishments like making a team or getting a driver’s license to something silly like a favorite TV show.

I look for ornaments that are sturdy and can hold up to toddlers and being jostled around in a box year to year. Avoid handblown glass ornaments or anything that can easily break. Look for ornaments year-round, when you travel or this time of year at local craft fairs or holiday events (see page 34), where many ornaments are handmade and often can be personalized on the spot. As a Michigander, I have to mention that Bronner’s Christmas Store (bronners.com) is the world’s largest Christmas store, and just about any ornament you can think of is a click away.

Start by giving a simply decorated box with the child’s name on it and one ornament inside. Let them know that you plan on adding to the collection every year and that the point is to keep their special ornaments in their own box so someday it will be full and ready to move out with them. I try to personalize and date ornaments (even if it means doing so myself with a Sharpie) so the ornaments don’t get mixed up with family ornaments.


Instilling generosity in your children is the cornerstone of the holidays. While kids can be in a frenzy drafting their own holiday wish lists, it’s important to teach them what a joy giving can be. Whether through donating to angel trees at a house of worship, participating in a toy or coat drive or working in a soup kitchen, the holidays are an easy time to remind children that for many others, a new coat or hot meal tops their wish list.

Teaching children to consider family is also important. When I was a child, the local Birmingham Community House was the highlight of my holiday season. It offered a holiday shop for children where, for a few dollars, I could choose from a wealth of presents for my whole family.

Greenwich offers a similar boutique at the Junior League of Greenwich’s Enchanted Forest (this year it will be held at Christ Church November 16 – 18). At the Children’s Giving Shop, volunteers guide young shoppers as they choose from reasonably priced gifts for family, friends and teachers. Gifts can be wrapped on the spot and kids leave ready to spread cheer.



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