High On Adventure - Featuring Photojournalist Larry Turner

Friday, February 8, 2019

RoxyAnn Winery

RoxyAnn Winery

Southern Oregon Magazine

Story by Pamela Ruhl Gibson

Photography by Steven Addington


RoxyAnn Winery is located at Hillcrest Orchard, one of the longest continually producing fruit orchards in Oregon. The property is located at the base of RoxyAnn Peak on the northern border of Hillcrest Road, just over two miles east of Medford’s business center. Hillcrest owns over 185 acres of fruit orchards consisting of pears, peaches, apples and grapes.

The 19th century barn that once housed horses and tack has been home to RoxyAnn’s tasting room for the past 15 years. Slated wood floors, warped with time, still embrace the story of Hillcrest Orchard and the Parsons family, who purchased the property in 1908. During the early 1900s, Maude and Reginald Parsons split their residency between Oregon and Washington with Hillcrest being their home for half of the year. In both states, the Parsons were a highly respected couple as contributors to the commercial fruit industry and to philanthropic enterprises. Their combined contributions to social welfare, schools, hospitals, and more resulted in benefits that residents of both Oregon and Washington still enjoy today. 

Twenty years ago, Maude and Reginald Parsons’ grandson, Jack Day, with a Harvard MBA in hand, decided to plant grapes on the southwest slopes of RoxyAnn Peak. He believed that the rich volcanic soil combined with the moderate and sunny climate of Southern Oregon would produce exceptional grapes leading to outstanding wines. In 2001, the first harvest resulted from a Bordeaux style varietal planted on the volcanic slopes resulting in the first 150 cases of Claret wines. The wine was so well received that it sold out within two weeks, and RoxyAnn Winery was established. 

With the promise of exciting new wines to share, the circa 1900 horse barn provided Day the ultimate space for a wine tasting experience. As the heart of the Hillcrest, the original stalls were converted into a small tasting room in 2003. The demand for RoxyAnn wine required the expansion into the entire barn.

Further renovations in 2006 allowed a central bar and more seating throughout the space. Double French doors on both ends of the barn provide natural, filtered light in the warm and inviting tasting room. The preservation of the original hand-hewn wood floors, walls, beams, and remnants of barn accessories create a unique experience in history and wine tasting.

Wine barrel tables provide comfortable seating and a friendly atmosphere to enjoy wine, music, food and friends. Seating is also available at the bar where guests can savor wine sampling or interact with the friendly and knowledgeable bar staff. This trendy tasting room easily engages the senses through architecture, hanging artwork and décor, all while savoring the tastes of accomplished wines. With a newly built outdoor pavilion, additional outdoor space is available to guests at RoxyAnn. The area provides a lovely space for small events and meetings. A live music series is held on the pavilion, June through September.   

The honor barn is located just outside the tasting room and offers a variety of fruit sales. Fruits are available for sale late July through December with peach sales starting in July and pear sales in early August. Payment for fruit is by the honor system. RoxyAnn offers a popular wine called “Honor Barn Red,” named for this historic means of payment.   

RoxyAnn Winery features weekly musical events on Wednesday, Friday and Sunday. The artwork of different local artists is displayed on the walls of the tasting room, featuring a new artist each month. RoxyAnn hosts many other events throughout the year, including the Annual Harvest Dinner, Crush Polio Grape Stomp, Blues, Brews, BBQs, and private events. Weddings are hosted by Hillcrest Orchard on the estate lawns and gardens. 

RoxyAnn Winery has won countless accolades and awards for their wines. Many changes have transpired since Jack Day’s time, and Day’s son, Chad, now manages the winery. The winery continues to employ the same family tradition through the delivery of an excellent wine, superior customer service, and hospitality. Jack Day’s original quest for outstanding grapes and a refined product did in fact materialize through the birth of RoxyAnn Wines.  


RoxyAnn Winery

3283 Hillcrest Rd, Medford



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