A “sweet” new business will soon occupy the space on the high side of Main Street, formerly housing Cheesecake & Company. “The Cake Carpenter” plans a soft opening on October 20 at 39 South Main Street.
The new shop’s owner is Sydney Carpenter (hence, the name “Cake Carpenter”). Sydney moved to Winchester from Lexington nine years ago when she married her husband, George, who is a Winchester native.

Preparation work was still underway at the shop when I visited on Friday. Although already well-equipped to operate as a bakery, Sydney and George were busy putting their own touch on the building. Pink dominates the color scheme.
Offerings at the new shop will include a range of delectable treats like cookies, cupcakes, cake slices, and brownies, as well as specialties such as chocolate-covered fruit, cheesecake-stuffed strawberries, and cheesecake-stuffed tacos.
Other offerings will include savory lunch fare such as wraps, salads, soups, and dips. For those with special dietary needs, there will also be daily gluten-free and vegan options.
Of course, patrons will need something refreshing to wash all of that down, and The Cake Carpenter has that covered as well. The drink menu will feature mixed lemonades, mixed teas, mixed iced coffees, and hot coffees.
“I’ve been here since we’ve been married in 2016, and my heart has literally grown for Winchester,” Sydney says.” Just this small community, how everybody comes together . . . I love the community!”
Besides the fact that the new space was already set up as a bakery, what drew Sydney to this particular location was the renovation of the high side and the patio space in front of the store.
“We will be open later, so people will be able to enjoy the desserts outside on the patio as well, getting the view of the lights coming off of the courthouse. So it’s gonna be so gorgeous!”
It’s evident that Sydney has a heart for young people and children, and she often brings up the notion of creating a “safe space” where everyone feels welcome and safe.
“I’ll have some encouraging messages, like a sign that’s come in that’s really encouraging. So just a safe space for people to go and just de-escalate, de-stress, relax. Those are the people I want to come and truly experience the love of God. And especially for the kids that come in, [they will] be protected and won’t be judged based on what [they] have on, what they look like.”

How did Sydney get started in the business of baking and cooking?
“Well, it was my mom. I started off making chocolate-covered fruit. And my mom’s like, ‘You need to put this out there.’ And I’m like, ‘No, it’s just chocolate fruit. People can get it anywhere.’
“Well, come to find out, the chocolate that I make, the blend is so perfect on the fruit that people really love it because it’s so smooth. So my mom pushed that, and then it turned into cupcakes. Cupcakes turned into cakes. My husband was like, ‘Your cakes are going to be your best seller.’ I told him, ‘I’m not making cakes.’ A year later, I was making cakes, and everybody was ordering my cakes.
“And so I took classes for pastry arts just to learn the science behind it as well. I love science and I love art. Desserts are where science and art come together.”

What is Sydney’s business philosophy?
“Quality. That’s one of the most important things to me. That and excellent customer service.
“We’re having a soft opening on October 20 because I do have a following on social media, and we don’t want to get overwhelmed. We’re family-owned—it’s just my husband and me, and another family member is going to help out.
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“And so that’s one promise I make to my customers. You’ll always have the best quality. If you don’t, I’ll fix it.”
How confident is Sydney that she will be able to open by October 20?
“I have high hopes . . . we’re getting a lot done today, and then over the weekend . . .”
Her voice trails off, and she flashes a hopeful grin.
