1997: Carrabassett Valley Academy expands by purchasing the Lumberjack Lodge for additional dormitory space.
2001: The $1.2 million Anti-Gravity Center physical training facility, jointly financed by the town and Carrabassett Valley Academy, officially opens in February. The 20,000-square-foot complex features a gymnasium, skate park, and locker rooms.
2002: On the 20th anniversary of its founding, Carrabassett Valley Academy announces plans to build a new and larger campus on 22 acres adjacent to its current location. The decision to expand comes in the wake of placing six skiers and snowboarders on the U.S. Olympic team and having former students Bode Miller and Kirsten Clark win medals in Olympic and world competitions. In all, CVA alumnae include eight Olympians, four world champions and 70 national champions.
2006: Carrabassett Valley Academy alumnus Seth Wescott wins a gold medal in the initial snowboard cross event at the Winter Olympics in Torino, Italy.
2007: Carrabassett Valley Academy opens the first phase of its expansion, a dormitory called Murfey Hall, allowing the school to sell the Lumberjack Lodge.
2008: Carrabassett Valley Academy names the newly expanded campus in honor of H. King Cummings, a founding chair of CVA. Cummings developed a school that enriched the community and gave student-athletes the opportunity to reach their highest potential.
2011: Kate Webber Punderson, a graduate of CVA's class of 1989, is named Head of School.
2014: The new 17,000 square foot state-of-the-art Webber Academic Center opens its doors. The center, which connects to the Murfey Residential building built in 2007, is named in honor of Peter and Martha Webber, members of the founding board of trustees who supported CVA throughout their lifetimes.
2016: Carrabassett Valley Academy is named US Ski and Snowboard Club of the Year, a gold-level award that represents the single highest honor in the US Ski & Snowboard organization, and US Ski and Snowboard Snowboard Club of the Year, a silver-level award. US Ski & Snowboard clubs provide the backbone for athletic programs, with coaches and dedicated volunteers providing the direction for athletes to succeed
2016: The new $2.1 million Bill and Joan Alfond Competition Center opens, featuring an 11,000 sq. ft. Competition Center that includes day lodge space, tuning and waxing facilities, locker rooms, a trainers’ room, meeting space, and offices. The project is a collaboration between CVA, Sugarloaf Resort, and the Sugarloaf Ski Club, with the purpose of fostering friendships, instilling a lifelong love of winter, and supporting athletes of all ages.
2016-2021: CVA, Sugarloaf, the Sugarloaf Ski Club, and other community partners continue to expand and improve training venues including terrain parks, a moguls course, a jump training site (Joanie's Jump), and a Cross Course developed by Olympian Seth Wescott ’94.
2022: The grand opening of the CVA/Colby Competition T-Bar is held. The venue offers wider training lanes and state-of-the-art snowmaking to optimize at-home training opportunities.