Down on Main Street: ‘The Cake Carpenter’ Will Bring Sweet Treats to Main Street

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Estimated time to read:

3–5 minutes

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.

Sydney Carpenter.
Sydney Carpenter proud­ly dis­plays the “open” sign that will soon grace the street-fac­ing win­dows at The Cake Carpenter.

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.”

inside the store
Pink is every­where out­side and inside the new shop. On October 9, the new look was com­ing togeth­er inside the store. 

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.”

Sydney Carpenter in front of her new shop, The Cake Carpenter.
Sydney Carpenter pos­es in front of her new shop, The Cake Carpenter.

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.

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