Mike Woolard
Board Member, Wintergreen Music
Mike Woolard was born and raised in Lynchburg, Virginia, one of four boys in a home filled with music thanks to his father, a music minister. From an early age, music was woven into the fabric of his daily life. From playing trumpet in the middle school band to playing bass guitar in a rock band in high school, Mike has had a lifelong appreciation for the arts.
While studying business at Lynchburg College, Mike joined the ski club, which brought him to Wintergreen for the first time. He quickly fell in love with both the sport and the mountain. In 1987, he began working part-time at the resort’s front desk and as a ski instructor—roles that deepened his ties to the community he would one day call home.
After graduation, Mike built a 20-year career in the restaurant and hospitality industry, working in the Poconos, PA, Durham, NC, and finally Charlottesville, VA. It was in Charlottesville that he was introduced to Virginia’s growing wine industry, which inspired a career shift. For the next 15 years, he worked with local wineries, helping them expand and grow their distribution.
All the while, Wintergreen remained a central part of his life. Mike taught skiing for decades, purchased his first Wintergreen property in 2005, and became a full-time resident in 2015. After earning his real estate license, he spent seven years with Wintergreen Realty before joining RE/MAX, where he continues to help families make Wintergreen their home; a role he considers his most rewarding.
Mike has a long history of community involvement at Wintergreen, including service as secretary and treasurer of his condo association board. As a property owner for more than 20 years and now a full-time resident, he brings both perspective and passion to community leadership.
Outside of real estate, Mike is a wine enthusiast, avid cyclist along the Blue Ridge Parkway, and enjoys hiking Wintergreen’s trails and skiing as often as possible. Each July, he looks forward to immersing himself in the Festival’s performances.
