This episode features a conversation with Taylor Simpson, one half of the second-generation team that now owns and operates two wineries on the Leelanau Peninsula in northern Michigan. The Simpson family first planted their roots on the Leelanau Peninsula in the 1950s when visionary entrepreneur John Simpson grew pears and plums for Gerber’s baby food. In the 1970s, he replaced the trees with cherries when that industry became more marketable. John then saw an opportunity for cool-climate wine and sent his son, Bruce, to study grape growing and winemaking at the University of California, Davis. The Simpson siblings have now expanded their reach beyond two family wineries creating Simpson Family Estates, which includes their winery businesses but also plays a critical role in the community by advocating for Michigan agriculture, supporting local wineries and wine trails and early childhood education for local children. Their winemaking operation, called Harbor Hill, supports other wineries across Northern Michigan through production and vineyard services and consulting. We talk about Taylor’s strong roots – literally – to the Leelanau peninsula even reminiscing about helping her mom in the tasting room after school growing up, but Taylor also lived the city life in Chicago after graduating from the University of Michigan. She worked in wine sales distribution for a large wine and spirits distributor, honing her knowledge of wine and business while traveling to renowned wine regions of the world. She carried this extensive experience back home with her and continues to expand the reach of their wines through direct to consumers channels in 17 states (and growing!), boutique and chain grocery stores, and Midwest restaurants. She focuses her marketing efforts on building brands that convey a genuine story of the people and places behind the wines. We hope this conversation sparks your interest in Michigan wine while also giving you some insight on what it’s like to be part of an up-and-coming wine region. You can visit www.simpsonfamilyestates.com to learn more about their winery portfolio and their viticulture practices, and you can visit www.michiganbythebottle.com to learn more about their satellite tasting room project.

Recorded August 5, 2025