About Us
Jack Day, the visionary grandson of Reginald Parsons, harnessed the grape-growing potential of Hillcrest Orchard Estate, recognizing its ideal conditions – sloping hills, clay soils, and abundant southern sunlight. Drawing on his expertise as an artisan farmer with an MBA from Harvard, Day orchestrated the planting of the original 20 acres on the southwest slopes of Roxy Ann Peak in 1997. Guiding the vineyard through its first harvest, he unveiled a remarkable proprietary red blend named “Claret,” which quickly sold out within two weeks.
Today, one of the premier Oregon wineries, RoxyAnn continues its legacy, producing nearly 15,000 cases of award-winning Southern Oregon wines. The diverse portfolio includes celebrated varietals such as Claret, Pinot Gris, Merlot, Cabernet Sauvignon, Cabernet Franc, Tempranillo, Syrah, and Viognier. Each wine is a testament to the region’s unique terroir, showcasing a harmonious blend of balance, complexity, and profound depth of flavor.
Our Great Team
At RoxyAnn Winery, we’re all passionate about vineyard management, winemaking, and customer service. When people visit our winery, we want them to feel welcomed and at home, like part of our family. We are proud to be an integral part of the historic legacy of Oregon wineries.
Chad Day
gm — owner
Following in his father's footsteps, Chad brings a unique blend of skills and a thoughtful management approach to RoxyAnn Winery. With previous experience in residential and commercial construction and a Master's in Business Administration from Seattle University, Chad returned to his hometown in 2012 to assist his father with RoxyAnn's fall harvest and oversee the family business. Chad and his wife, Oakley, have two young daughters who can often be seen playing with their cousins on the property. As part of the vibrant tapestry of Oregon wineries, RoxyAnn reflects Chad's commitment to preserving and advancing the winemaking tradition in the region.
Crissie Olson
cfo — owner
Despite knowing she always wanted to work for the family business, Crissie pursued her education and career, completing her undergrad in Southern California and earning her CPA and MBA in Portland. After working in public and private accounting, including as a controller in the retail/manufacturing industry, Crissie gained the experience needed to join RoxyAnn Winery. She and her husband, Shaun, along with their three children, have since moved back to Medford, living close to the tasting room and extended family.
Fred Mihm
winemaker
Fred discovered his passion for wine while assisting friends in renovating a neglected Medford vineyard after completing a BA in Literature from Portland State University. He started as a cellar rat at Weisinger's, quickly advancing to become an Assistant Winemaker. Fred also gained valuable experience working with world-renowned winemakers, including Andrew Rich of Andrew Rich Cellars in Oregon and a winter crop harvest in New Zealand. Eventually, Fred joined the RoxyAnn Winery team. He lives in Jacksonville with his wife, Fiona, son Benjamin, and their dog, Pepe. He is proud to put his expertise to good use while bringing his unique skillset and passion to the scene of Oregon wineries.
Our History
One of Southern Oregon’s oldest orchards, Hillcrest Orchard, has been directed by members of the Parsons family since 1908.
the beginning
1853
Land settled by RoxyAnn and Samuel Bowen.
land sold
1868
Land sold to Jesse Richardson.
hillcrest orchard
1903
Julian Wells Perkin purchases a flourishing Apple and Pear Orchard and names the farm Hillcrest Orchard.
new owner
1908
Reginald H. Parsons bought Hillcrest Orchard and soon makes it one of the finest orchard complexes in Southern Oregon.
honor barn built
1918
The “Honor Barn” was built.
orchard renovations
1938
All apple trees removed and replaced with pears.
varietals planted
1997
20 acres of Vineyard planted in Block 14.
varietals planted
2001 welcoming claret
RoxyAnn Winery is born with the production of 200 cases of Claret.
present day
Today
RoxyAnn Winery has 70 acres of vineyard land in production and produces 13,000 cases comprising of 17 different types of Bordeaux and Rhone Style wines.
future generations
FUTURE
We hope to continue our families tradition of farming this land for the next generation to enjoy.
