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541 Wiley Parker Road
Jackson TN 38305


Woodstock Bake Shop: Finding Triumph in the Toil


Woodstock Bake Shop: Finding Triumph in the Toil

Guest Contributor


Before opening his bakery’s doors, Matt Childress spent several years racing cars competitively. Because of his competitive background, he grew up knowing he didn’t want to work a “normal job.”

He took his love for vintage aesthetic, his mom’s cake recipes, and his dad’s idea for a name—Woodstock Bake Shop—and ran with it. September 11, 2012 he opened for business on Innsdale Cove in Jackson. 

In those early months, Matt said there were more rough days than easy ones—from hiring friends who disappointed him to just being patient with the drudgery of starting a new business, it was more of a struggle than he expected.

“I made a ton of mistakes,” he said. “It takes a long time and a lot of persistence to build a business. I’m a very competitive person, so I knew I was going to figure it out. I just didn’t know how long it would take to figure it out.” 

Matt wasn’t prepared for the downtime at the end of the day as a young entrepreneur, according to his dad Dale. Just twenty-two years old at the time, he would often come home and start to question himself. Am I really prepared for this? What happens if I fail?

“In the beginning, we would have days where ten or fifteen people would walk through the doors,” Matt said. “Now it’s a few hundred every day. You just have to hang in there for the first two or three years.” 

Matt said he learned that those in his sphere of influence—although they would never admit it—weren’t always rooting for him to succeed. People didn’t want him to be more successful than they were, he said. 

One thing that helped him stick with it was avoiding social media. Both strangers and friends would talk negatively about his plans on Facebook, and it took him a long time to learn to ignore it, but ultimately he refused to let those people tear him down.

Now twenty-five years old, Matt has learned from his mistakes and seen his business expand to three Jackson locations in just three years. He’s also seen his own confidence level grow and his love for business develop.

In addition to the original Innsdale location, Woodstock has a booth downtown at the farmers' market and recently launched a spot at Jackson State Community College.

“A lot of people thought we had deep money somewhere, but it was a big risk,” he said. “We took a leap of faith, and it worked. I like to just commit to something and then figure out the rest later. Sometimes you make mistakes, but sometimes you make great decisions.” 

I like to just commit to something and then figure out the rest later. Sometimes you make mistakes, but sometimes you make great decisions.
— Matt Childress

One thing that has kept Woodstock’s business afloat is their commitment to a community-minded mission. Dale said that since day one their love for the community has not dissolved—although it may have taken people a while to realize their authenticity. 

Woodstock chooses a local charity to support each week—from St. Jude Children’s Hospital to Madison Academic’s Soccer Team. They set out a donation jar throughout the week, and twenty-five percent of Saturday sales go directly toward that week’s organization.

“People buy from people they like, trust, and believe in,” Dale said. “They won’t if they don’t see you genuinely doing things to make the community better. Anybody can sell a cupcake, but I don’t think anybody can reach out to the community like that.” 

Anybody can sell a cupcake, but I don’t think anybody can reach out to the community like that.
— Dale Childress

At times, Woodstock would be giving more money away than they were making, but they never wavered from that mission. Matt said he believes the more you receive, the more you should give back. 

Woodstock’s mission plays nicely alongside its theme in promoting peace and love. At first glance, one notices vibrant colors, vinyl records, groovy posters, and tie-dyed t-shirts. But once you hang around a little longer, you start to pick up on the Childresses’ attention to detail. 

Tens of thousands of customers’ signatures adorn the walls. Dale said the original plan was to line the walls with art, but they couldn’t afford that in the beginning. Now people stop in from the interstate just to buy a cupcake and sign the wall, he said.

Displaying about eighteen different cupcake flavors on any given day, Woodstock allows their customers to name the treats on Facebook: Proud Mary, Stairway to Heaven, Kokomo, and Susie Q, among others. 

Dale spends a lot of his time writing inspirational quotes on every single box that goes out, which is typically hundreds every day. People will send him messages, or he will search for them online. With a database of more than 1,000 quotes stored in his iPad, the likelihood of ever getting the same one is slim to none.

“That late 60s, early 70s genre is all about peace and love,” Dale said. “I was around back then, and we didn’t promote war. It was all about togetherness and unity. You don’t see much of that anymore.” 

But when running a family business, it’s not always peace and love, right? That’s not the case with the Childress family. They seem to have found a balance of work and family life, and even after the two each put in eighty hours of work a week, the family dynamic doesn’t bring issues. 

“Most family businesses, you hear about them fussing and fighting,” Dale said. “We know our roles. I handle the marketing and community side, and Matt handles the business side.” 

Matt wakes up at 5:00 a.m. to starting preparing for each day at different Woodstock locations. By 6:00 p.m., he closes up and heads home for the night, leaving his laptop behind so he doesn’t have to think about work. 

In the spring, Woodstock is set to launch a food truck. Matt said he’s interested in expanding to more college campuses in the area, and ultimately he wants to open a store in Las Vegas. 

“We just don’t sit still,” Dale said. “We don’t let a slow day deter us from where we’re going. We keep finding new ways to grow.” 

Say hello to Matt and Dale next time you stop by for a boxed lunch, cupcake, cake ball, or any other Woodstock Bake Shop treat!

To learn more about Woodstock Bake Shop, visit their website, and make sure to follow them on Facebook, Twitter, and Instagram. Visit them at 80-C Innsdale Cove (Monday through Saturday), at the West Tennessee Farmers' Market downtown (Thursday through Saturday), or at Jackson State Community College (Monday through Friday).

Danica Smithwick is a senior journalism major at Union University, where she serves as Editor-in-Chief of the Cardinal & Cream. Otherwise, her life in Jackson consists of writing for the Jackson Sun, attending City Fellowship Baptist Church, and shopping for used books that she struggles finding time to actually read. She probably talks about Myers-Briggs and ice cream more than anything else.

Photography by Danica Smithwick.