Experience
A Premier Grower of Walla Walla Fruit
History of Farming and Winemaking
1979 – First planted vine
1981 – Estate became commercial vineyard
1994 – Vineyard split into two properties – Seven Hills Vineyard and Windrow Vineyards
1996 – Hill Block Cabernet Sauvignon and Mary’s Block Malbec were planted
2007 – Doug & Jan Roskelly & Mike Tembreull purchased the property and opened Tero Estates
2022 – Samantha Maiden & Karra Blair purchased the Vineyard and formed Windrow Estate.
2025 – Reopens under Windrow Estate Winery
“Moving home and getting to be the caretaker of these vines is something I would have never imagined. It just feels right.”
Samantha Maiden
ESTATE MANAGER
SAMANTHA MAIDEN
Samantha was born and raised in the Walla Walla Valley. After graduating from Wa-High, she moved to Portland and pursued a career in the funeral service industry. During her time in funeral service, she developed a deep appreciation for bringing people together to celebrate good times and bad. After 10 years and providing care for 1000’s of families, she went back to school to get her M.B.A. From Marylhurst University. While attending school, she was presented with an opportunity she could not pass up to purchase a wedding and event center in Milwaukie, Oregon.
Samantha’s love for planning personalized events demands attention to detail and strict standards for quality. Helping people during their most difficult times demanded her to be at her best daily. Her passion for meaningful moments made her a leader in both industries. Her love for her family and hometown are what drew her to back to Milton- Freewater.
When Samantha isn’t busy creating, you can find her spending time with her husband Andrew and their two boys, Henry and Simon, cooking, or daydreaming about her next wine tasting adventure.
KARRA BLAIR
Karra is a lifelong Oregonian, born and raised in Portland. She started her professional career in public accounting where she earned her CPA license, followed by various accounting management and executive leadership roles. Her passion and enthusiasm for wine led her to purchasing Windrow Vineyards with Samantha in 2022. From their first visit to the property, she knew how extraordinary this place was and how special it would be to share it with others.
In her downtime, Karra enjoys traveling and seeking out new adventures with her husband Trenton, supporting her two stepdaughters (Lilly and Violet) in their many activities and personal growth, and spending time with her family and friends.
BRIANNA JAMES
Brianna has called the Walla Walla valley home for over 20 years. A proud graduate of DeSales Catholic High School, she got her start in the wine world at 21, pouring and bartending at several local establishments where she discovered a passion for hospitality and the stories behind each glass. That early experience laid the foundation for her work at Windrow Estate, where she blends hands-on knowledge with fresh insight as she pursues a degree in Business Marketing.
Outside of Windrow, Brianna is an avid gardener, a proud member of both the women’s and co-ed city softball teams, and a devoted mom raising two sons (Ashaunte and Shiloh) in the community she loves. She brings warmth, drive, and a genuine connection to her work, and she’s proud to be part of a team that celebrates great wine and local roots.
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