This young baker tore up the instructions for starting a business (but kept all the best recipes)

Overland Park cookie shop gets a new baker behind the counter, adding a frosted twist to familiar favorites

She learned to bake as a child by her grandmother’s side.

So by middle school, Maddie Callicott was so proficient she not only held popular bake sales, she printed up business cards for her “You Take the Cake” operation to generate more orders from family and friends.

Maddie Rae’s at 9224 Metcalf Ave., Overland Park; photo by Joyce Smith

Since then she’s gained formal training and stints at several Kansas City bakeries, including Connie’s Cookies in Overland Park.

Now, after nearly two decades, the Connie’s Cookies sign is down, and the Maddie Rae’s Bakery sign will soon be up as Callicott moves from a former employee to owner.

Click here to follow Maddie Rae’s Bakery on Instagram.

“This has been my passion so I definitely had hopes this would come to fruition,” she said. “Owning a bakery has been my dream.”

Still, it wasn’t a straight path to becoming a business owner.

Maddie Callicott greets customers inside the new Maddie Rae’s Bakery; photo by Joyce Smith

Just keep going

Maddie Callicott baking at home as a teen; courtesy photo

Maddie Callicott as a child; courtesy photo

Callicott crafted cookies, cakes, candy bark and even the occasional family dinner with her grandmother, Carolyn Callicott, “a wonderful cook and baker.”

While at Shawnee Mission South High School, she enrolled in what is now called the Culinary Arts and Hospitality Signature Program. The students operate the Broadmoor Bistro at 8200 W. 71st St. in Overland Park.

Her dream of owning a bakery took the first detour when she signed up for journalism courses at Kansas State University in Manhattan, Kansas. But she missed her family — and baking.

A tour of Johnson County Community College’s culinary program set her back on the bakery path.

In 2015, while earning a pastry/baking certificate, she joined Connie’s Cookies at 9224 Metcalf Ave., Overland Park. When the owners wanted to expand beyond cookies in 2017, she offered up her cinnamon rolls.

During college she also spent six months studying in a bakery and pastry program in Florence, Italy — that included six weeks working in a bakery.

Maddie Callicott outside the Wylie Hospitality And Culinary Academy at Johnson County Community College; courtesy photo

When the original owners of Connie’s Bakery sold the business in 2018, Callicott stayed for a month to help with the transition. And while she would have liked to purchase the shop, the then-22-year-old knew she needed more experience.

Her first stop: Heirloom Bakery & Hearth, a Brookside full-service bakery with a fast-casual service style.

“To learn their production versus just a cookie shop. More variety. How to be more efficient,” she said. “Getting up at 3 a.m. and working until 11 a.m. and it was a lot of fun because I got to do a lot of different recipes.”

Next she joined Rye on the Country Club Plaza to get full-service restaurant experience.

But then came another diversion.

Her father, Kent Callicott, owns Petworks Veterinary Hospital, next door to Connie’s Bakery. 

Maddie worked there off and on since she was 15, and they needed help. So after Rye, she earned a veterinary certificate and joined the family business, later moving into management.

When COVID hit the metro, she was considered an essential worker and stayed employed, unlike many restaurant workers.

In late 2024, she heard neighboring Connie’s Cookies was going to close. She sat down with the owner, worked out an agreement including taking over the seven-year lease, the name, recipes and equipment. The deal was finalized in early December, during the holiday rush.  

“It was a crazy, hectic time but it was good,” she said. “I’ve always loved this place and wanted to keep it going.”

Maddie Callicott talks with her father, Kent Callicott, who owns Petworks Veterinary Hospital, next door to Maddie Rae’s Bakery; photo by Joyce Smith

Back and baking

Maddie’s uses the same recipes that made Connie’s Cookies a draw for nearly two decades: chocolate chocolate chip, lemon, M&Ms, oatmeal raisin, peanut butter, Snickerdoodles, sugar cookies, and more.

It also features a cookie of the month; most recently: oatmeal frosted.

Maddie’s favorite? The sweet and slightly salty M&Ms.

The shop is known for its cut-out sugar cookies that can come in more than 150 different shapes — angel, cat, stroller, watermelon, tooth, KC helmet, butterfly, bikini, rainbow, and basketballs. They are hand-rolled, hand-cut and hand-frosted with tinted buttercream. To welcome spring, Maddie offered pastel yellow, orange and green colors.

Sugar cookies frosted in spring colors at Maddie Rae's Bakery; photo by Joyce Smith

Cinnamon rolls from Maddie Rae's Bakery; photo by Joyce Smith

Her work day typically starts before 7 a.m. She does all the baking, frosting, packaging, waiting on customers, and then prep for the next day. She’s usually home by 7 p.m.

Her mother, Angie, occasionally helps out by waiting on bakery customers, while her father will put on an apron and pop in to work in the kitchen — to the surprise of his veterinary customers.

“People will be like, ‘Is that Dr. Callicott back there?’” Maddie said. “We joke that we will put in a pass-through window between the businesses. But it is rewarding to work with family.”

She’s also already brought back the cinnamon rolls and added coffee cake crumble muffins. Lemon poppyseed, and chocolate chip zucchini muffins could soon make the menu. And she’s seeking feedback from customers.

Her bakery is continuing to take pre-orders while also now packaging treats for walk-in customers.

She also recently took a cookie order for a high school graduation party that didn’t want the typical cakes. She can package cookies individually or displayed on trays.

Only one issue so far as owner: the AC is out, not something to notice during the metro’s blustery winter, but in a hot kitchen on a recent 70-degree-plus day? The temperature can hit 100.

A small sign at the new Maddie Rae’s Bakery in Overland Park; photo by Joyce Smith

As for competition, she cites Overland Park’s The Upper Crust Bakery and McLain’s Bakery — both two or more miles away, along with a few chain shops.

But Maddie’s Bakery is in a pocket with surrounding office tenants, an area she calls “up and coming” with a lot of new development including 95Metcalf, the former Metcalf South Shopping Center just down the street. She also has a food truck that she hopes to roll out soon.

She kept the Connie’s Cookies name during the transition so customers would know she was honoring the legacy. But after four months it was time, “to put my own stamp on it. My customers have been very supportive of the transition,” she said.

Hours are 9 a.m. to 5 p.m. Tuesdays through Fridays, and 9 a.m. to 3 p.m. Saturdays. The shop is closed Sundays and Mondays; customers can pick up pre-orders on Mondays by appointment.

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Startland News contributor Joyce Smith covered local restaurants and retail for nearly 40 years with The Kansas City Star. Click here to follow her on Bluesky, here for X (formerly Twitter), here for Facebook, here for Instagram, and by following #joyceinkc on Threads.