Behind the Scenes of Sweet Martha's Cookie Jar at the Minnesota State Fair
Fashion

Behind the Scenes of Sweet Martha's Cookie Jar at the Minnesota State Fair

authorBy Gloria Vanderbilt
DateSep 06, 2026
Read Time4 min

Jennifer Olson, a prominent figure at Dôen, dedicates a portion of her summer each year to a cherished family tradition: managing Sweet Martha's Cookie Jar at the Minnesota State Fair. This enterprise, founded by her parents in 1979, has evolved into an iconic fixture of the fair, renowned for its freshly baked chocolate chip cookies. Olson's narrative offers a unique glimpse into the intensive preparations, the logistical complexities of producing millions of cookies daily, and the deep-rooted family involvement that sustains this beloved institution. It's a tale of entrepreneurial spirit, community, and the enduring appeal of a simple, delicious treat.

The legacy of Sweet Martha's Cookie Jar began in 1979, conceived by Martha Rossini, Gary Olson, and their friend Neil O'Leary. Martha, growing up near the fairgrounds in St. Paul, nurtured a lifelong passion for baking with her grandmother. Initially, her entrepreneurial endeavors led to Sweet Martha's Yogurt Shop. The leap to the Minnesota State Fair was unexpected; their yogurt proposal was declined, but the cookies were enthusiastically accepted. This pivotal moment led to the creation of the now-famous chocolate chip cookie recipe, a blend of cherished family recipes. From a modest 9' x 11' backyard-built plywood booth, the operation has expanded to three permanent locations across the Fairgrounds, celebrating its 47th year of operation.

Preparing for the Minnesota State Fair is an extensive undertaking that commences in February, ensuring everything is in place for the late August opening. This involves recruiting over 750 staff members, many of whom are students returning to school. The logistical coordination is meticulous, with Katie Atlas, a childhood friend, overseeing the complex scheduling. Each of the three stands undergoes thorough cleaning and stocking. Ingredients are delivered fresh nightly, maintaining the commitment to baking from scratch and serving cookies straight from the oven. The seasoned crew, many of whom return year after year, ensures a smooth and efficient operation, perfected over four decades.

A typical day for Jennifer Olson during the fair begins early, around 7 a.m., to prepare the booth for an 8 a.m. opening. The morning starts with a serene 'Classical Hour,' a brief period of calm before the bustling crowds arrive. Production is immense: each mixing bowl yields 5,000 cookies, and with 22 walk-in ovens capable of baking 2,000 cookies simultaneously, Sweet Martha's can produce 44,000 cookies in just 12 minutes. Daily production averages one million cookies, soaring to three million on peak days. Over the 12-day event, staggering quantities of ingredients are used: 197,000 pounds of sugar, 143,000 pounds of flour, 125,000 pounds of chocolate chips, and 58,000 pounds of eggs.

The family involvement in Sweet Martha's is a cornerstone of its success and identity. Jennifer hails from a large family, with numerous aunts, uncles, and cousins contributing to the annual cookie production. Over 20 family members typically work each year, transforming the fair into an annual reunion. Neil O'Leary, the co-founder, also brings his extensive family to help. Jennifer's brother, David, works in lockstep with her, and his wife, Erica, manages public relations. Cousins like Lucia, who runs employee engagement and creates TikTok content, and Will, an engineer who developed a mathematical system for oven management, play crucial roles. Even Jennifer's husband, Aidan, and his parents are integral to the operation, underscoring the deep family commitment.

Beyond the cookies, Sweet Martha's has cultivated a distinctive brand presence, particularly through its merchandise. The journey into branded apparel began with a unique collaboration with Vampire Weekend, which stemmed from Ezra Koenig and Jake Longstreth featuring Jennifer's mother on their podcast. This led to a one-off T-shirt sale in 2019, with proceeds benefiting the St. Paul Public Library, a cause dear to Martha. During the 2020 pandemic-induced fair cancellation, the official merchandise line was launched, starting with tie-dyed tees. Guided by industry veteran Aaron Levine, the line expanded to include collaborations with other bands like The Black Keys and LCD Soundsystem, with a continued commitment to supporting the library. This blending of family business with Jennifer's passion for music has created a vibrant and engaging brand identity.

The true essence of Sweet Martha's lies in its community, especially its dedicated employees. With over 700 staff members, predominantly aged 16 to 21, the workplace fosters a dynamic and engaging environment. Jennifer cherishes the interactions, learning about current trends and appreciating the diverse skills each individual brings. The senior staff, many of whom are professionals taking time off their regular jobs, are equally vital. Jennifer's aunt Mary, a public school teacher, exemplifies this dedication by assisting in the evenings. These individuals, whether relatives or not, form an extended 'cookie family,' whose unwavering support is indispensable to the operation's success.

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