Meet the New Canaan entrepreneur turning gatherings into unforgettable experiences.
With a career that began as an orthopedic surgery assistant, Jayne Benton never imagined she would one day run her own event planning business. After stepping away from medicine to raise her two sons, Benton devoted herself to volunteering in the community—a path that unexpectedly led her toward a new career.
The turning point came when a friend running a charitable foundation asked Benton if she’d be willing to donate a cupcake baking class as a live auction item. The friend knew Benton’s creative talents firsthand. For years, Benton had dreamed up imaginative parties for her children, handling everything from the baking and elaborate decorating to the creative details that brought each celebration to life. She also regularly volunteered her talents for class and team events and was known for baking and creating alongside her own children and the neighborhood kids. Still, Benton was unsure whether anyone would be interested. She was surprised when “Baking with Jayne” became the most sought-after item of the night.
Inspired by the response, Benton began teaching baking classes at the New Canaan Library through the Parks and Recreation Department, and at after-school programs throughout New Canaan, Darien and Greenwich. “At one point I was baking more than 250 cupcakes every week,” says Benton.
As her children grew, so did Benton’s involvement in the community. Holding board and committee positions on every organization from her children’s schools to nonprofits like New Canaan CARES, she found herself increasingly drawn toward organizing fundraising events. Those experiences also marked a shift in her business, moving beyond children’s baking classes and toward more adult-focused celebrations.
“My first private event was helping to plan a 40th birthday party for a friend,” says Benton. “From there, things just expanded organically and it’s been word of mouth ever since.”
Today, Benton designs everything from engagement parties and milestone birthdays to corporate events and galas. Over the past year, she has helped plan the 10th Anniversary Waveny Park Conservancy Gala and the inaugural New Canaan Land Trust Legacy of the Land gala.
“I can’t believe I get to do this,” says Benton. “I get to see my friends, my kids, this community—and create experiences that people remember.”
Setting the Tone
Floral arrangements, linens and color palettes are often what people think about first when it comes to planning an event but Benton encourages her clients to start somewhere deeper.
“The biggest thing people forget is to lead with the feeling—not with the flowers,” says Benton. “I always ask people what they are trying to create, what they are celebrating and what feeling they want their guests to walk away with. We talk about what tastes and smells they want to include and people always have an answer. That’s when I start to get excited.”
These initial conversations become the foundation for every decision that follows, from selecting the perfect venue and choosing décor and design elements that bring the overall experience to life.
The Smallest Details
Whether the goal is festive, intimate, nostalgic or glamorous, Benton believes the emotional vision should guide every element of an event. Rather than defaulting to traditional venues, she often encourages clients to consider unexpected spaces that allow guests to connect more deeply with the purpose behind the celebration.
For a recent event, Benton transformed a firefly sanctuary into a magical evening setting, despite having virtually no electricity. Guests followed softly lit lanterns down wooded paths, cocktails were crafted from a trailer hidden among the trees and carefully placed lighting preserved the natural beauty of the fireflies without disrupting the surroundings.
“It was an experience—and that’s what people remember,” says Benton.
For Benton, creating that kind of memorable experience also means making sure an event feels deeply with the purpose behind the celebration.
Benton drew on his love of the outdoors, incorporating his collection of vintage décor and mounted pheasants into the design. “He loved it because it reflected who he was,” she says. “That’s the vibe I’m always aiming to create.”
Benton says the experience should start before guests even walk into the party. Whether it’s live acoustic music greeting people at the door or valet attendants dressed in themed attire, she believes it’s the unexpected touches that make an event memorable. “It’s the little surprises and hidden details that people discover throughout the night that set the tone and stay with people.”
A Family Affair
Although Benton is the creative force behind every event—from the initial planning to execution—she is often supported by her husband and sons. “My secret weapon is definitely my family,” she says. Her husband Tom helps manage invoices and logistics for the business and her sons have grown up lending a hand, helping with everything from building backdrops and transporting décor to pitching in wherever an extra set of hands is needed. “It’s always been a family effort,” she adds.
Follow Benton on Instagram
@elmstreetevents to see what she’s planning next!