Dec. 16, 2025

Dutcher Crossing: A Family Story, a Bold Ask, Buying the Winery That “Wasn’t...” Pt. 2

Dutcher Crossing: A Family Story, a Bold Ask, Buying the Winery That “Wasn’t...” Pt. 2
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Dutcher Crossing: A Family Story, a Bold Ask, Buying the Winery That “Wasn’t...” Pt. 2

In Part 2 with Debra Mathy of Dutcher Crossing Winery, we unpack the story behind the winery’s iconic penny-farthing bicycle logo.

Why Dutcher Crossing’s logo is a Penny-Farthing (high-wheel bicycle) and what it represents

The deeply personal origin story: a 2005 gift from Debra’s father, and the last gift before he passed

The reality of riding a penny-farthing (parades, tight turning, and “kids running out” moments)

The buying story: comparing every winery to Dutcher Crossing… even when it wasn’t for sale

Family advice that changed everything: “Go ask. The worst they can do is say no.

Negotiation moment: playing it cool outside the door while someone checks football playoff scores

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