Past & Present

Above: A pine wreath hangs from the front door of the O’Reilly home, built in 1760.

Jennifer O’Reilly bundles the charms of the holiday season in her historic Westport home.

The holiday season is a special time of year for decorating, oftentimes incorporating family traditions. For Jennifer O’Reilly’s historic Goodsell- Grumman Toll House in Westport, the tree, wreathes and vignettes are more than to-dos for the season; they’re all inspired by her love of family, history and place. She adorns her home with festive string lights, Santa and reindeer figures, snow-white garlands and fragrant pine wreaths. Among the traditional decorations, she adds a touch of character and good humor: Buddha statues, ’70s-vibe peace signs, wine corks spilling from a fireplace, and a framed picture of her friend and hometown hero, the late Paul Newman.

Jennifer O’Reilly with daughter Keleigh

Of her family, she says, “We are huge fans of Christmas. In fact, when I was first looking at this house to buy and renovate, it was August and one of the first things my sister Kelly said was, ‘This is the perfect Christmas house.’ ” Each year, Jennifer proves her sister right.

Usually, Jennifer embraces a fresh and modern sensibility, but around the holidays, she blends old and new as well as solemnity and cheer. “This jewel box of a home was built in 1760, while we were still paying taxes to the British, by the first family of the Greenfield Hill Church. I am humbled and awed to imagine the hundreds of Christmases that have been enjoyed here, before we were lucky enough to do the same.” Her gratitude and love is on full display as she adds to the home’s story.

Fireside Cozy
“I start ‘dressing’ the house, inside and out, the day after Thanksgiving. It allows us to really enjoy each moment of the season leading up to the big day, as opposed to just one day. Christmas music—and only Christmas music— plays, too. This is law.”

Around the Tree
“Growing up, my mom gave each of us an ornament at Christmastime. It was always something unique and relevant to each of us. For me it was a ballerina or maybe something from a place we had visited that year. When I started my own family, my mom gave me the collection of my childhood ornaments, and I have done the same with my children.”

On the Mantel
“Another tradition, some have called it an obsession, is the thousands and thousands of lights that I insist on. I had very good friends growing up here in Westport whose mom used to ‘braid’ the lights in and out on the branches, and the result was worthy of Rockefeller Center.”

By the Windowpane
“I haven’t really touched the dining room, out of the respect to the many spirits who have walked on these original chestnut wood floors in this tavern-like space. The cliché ‘If these walls could talk’ is oh so perfect for a room like this. I imagine all the loved ones [who were] served meals made in the living room’s walk-in fireplace—that space served as the kitchen in the eighteenth century.”

A Pop of Fun
“Now to the corks! It is a working fireplace, but it is very shallow and third-degree burns are not a guest’s favorite. One of my favorite restaurants on Nantucket is in a beautiful antique house. Each time they open a bottle, the cork gets tossed into the fireplace. I borrowed that idea from there, and, luckily for me, I have local friends who help me with my collection.”

A Christmas Toast
“The antique piece in our dining room served as a bedroom bureau in our last house. It has a secret drawer with a secret keyhole that was perfect for hiding jewelry and important papers. In its new life in the dining room, it now serves a much more vital purpose as a bar, just within reach of the dining table, and holds (too many) table linens. The oversized Ralph Lauren lamp makes the room even cozier when candlelight isn’t enough—and makes up for not having a chandelier because of the ceiling height.”

Beloved Memories
“I love to mix tradition with contemporary— something unexpected and whatever ‘speaks’ to you, not following rules. I love the mix of the modern bar cart beneath the wall of black-and-white photos of my parents, grandparents and son. The duo in the center is a nod to Paul Newman, a great family friend and my daughter’s godfather. These loved ones, all known to enjoy an adult beverage, get a wink and glass raised to them nightly.”

All photographs by Kyle Norton.

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