Enjoy tennis and pickleball year-round at Wintergreen!
Our facilities at both Devils Knob and Stoney Creek, feature a total of 16 clay tennis courts and three indoor DecoTurf tennis courts, along with six temporary indoor pickleball and eight new permanent outdoor pickleball courts.
Tennis Magazine has ranked Wintergreen among the nation’s top 50 tennis programs for the past 18 years. Tennis Resorts Online ranks it in the top 25 of tennis resorts worldwide, top 15 of Pickleball Resorts and top 15 Tennis camps.
Racquet Sports Facility is only available to Wintergreen Club Members, Guests of Members and Wintergreen Resort Lodging Guests.
For more information or court reservations, call 434-325-8345.
| PARTICIPANT | Indoor | Outdoor |
|---|---|---|
| Club Members (60 min) | $20 | $12 |
| Club Members (90 min) | $32 | $20 |
| Wintergreen Lodging Guests (60 min) | $32 | $20 |
| Wintergreen Lodging Guests (90 min) | $48 | $32 |
| Unlimited Club Members | $180 |
| Wintergreen Resort Lodging Guests | $220 |
Play better and save money with our new 1+1+1 lesson package.
This package includes 2 one-hour private lessons, one clinic session, plus get to try the new video analysis for one stroke type. During your one-hour lesson with Ryan, he will video the stroke of your choice and provide feedback for improvement. Improvement goals will be shared with our other Pro’s for consistency on your personal goals and objectives.
Part 1 – 1 one-hour private lesson with Ryan Fleming, Director of Racquet Sports, plus 1 stroke video analysis
Part 2 – 1 one-hour private lesson with another coach
Part 3 – 1 ninety-minute session in a coach led group clinic
To get started, call the Racquet Sports front desk or email Ryan to schedule your first lesson.
434-325-8345
[email protected]
Wintergreen Racquet Sports Facility has recently added eight permanent Pickleball courts, to the six temporary indoor courts for a total of fourteen courts on the mountain.
Pickleballer’s can take advantage of private reservations, private lessons, clinics such as Morning Madness and Train Like a Junior, and organized point play in Member Appreciation.
Wintergreen Resort is thrilled to welcome Ryan Fleming as our new Director of Racquet Sports. Ryan brings with him more than 30 years of experience as a player, coach, and leader within the tennis industry, along with a deep passion for fostering community through racquet sports.
A native of the mountains of North Carolina, Ryan was a standout collegiate player for legendary coach Chuck Kriese at Clemson University before competing professionally. Over the years, he has held numerous leadership roles, including Director of Tennis at The Birchwood Club, Adult Director at College Park Athletic Club, and most recently as Regional Director and Head of Staff for TennisBloc, where he managed and trained hundreds of coaches across the Carolinas.
Ryan’s extensive background combines business acumen, player development, and education. He has founded his own tennis school, collaborated with national coaching organizations, and worked closely with renowned tennis educator Steve Smith for more than two decades. Ryan has already developed an exciting lineup of new programs for Wintergreen’s racquet community, bringing fresh energy and a long-term vision to the mountain.
Now settled in at Wintergreen with his wife and children, Ryan looks forward to growing all aspects of racquet sports from tennis and pickleball to events and programming.
Phil’s passion for tennis began at an early age through his father’s tennis program, where he first developed the foundation for what would become a lifelong dedication to the sport. Immersed in tennis from a young age, he not only competed but also studied the game’s technical, tactical, mental, and emotional dimensions, cultivating a well-rounded understanding as a student of the game.
Since beginning his professional coaching career in 2008, Phil has worked with players of all ages and abilities, helping them develop their skills and confidence on court. Before joining Wintergreen, he lived and worked in Tucson, Arizona, contributing to a number of respected tennis facilities and earning a reputation for his player-focused teaching style.
Now at Wintergreen, Phil brings his deep respect for the game, a lifelong love of learning, and a genuine passion for helping players reach their full potential on the court.
Coach Gretchen Rush brings a wealth of experience and expertise to the court as a former professional tennis player and accomplished collegiate athlete. A standout competitor on the Women’s Tennis Association (WTA) tour, she amassed 191 singles wins and 193 doubles wins, highlighted by quarterfinal appearances at prestigious tournaments like the US Open, French Open, Wimbledon, and the Australian Open.
In 1988, she was a mixed doubles finalist at Wimbledon. Representing the United States at the 1984 Olympic Games, she achieved a career-high ranking of 13th in singles and 16th in doubles.
Coach Rush’s collegiate career at Trinity University in San Antonio, Texas, was equally impressive. A four-time All-American and NCAA Division I doubles champion, she twice reached the finals in NCAA singles and doubles. Her senior year was capped by winning the Broderick Award as the nation’s top collegiate tennis player. Under her leadership, Trinity made four Final Four appearances.
After retiring from professional tennis in 1992, Coach Rush transitioned to coaching, sharing her knowledge and passion for the sport. She has served as an assistant coach at San Diego State University, head coach at Our Lady of Peace High School, and head coach at San Diego City College and Claremont-Mudd-Scripps. From 2015 to 2020, she returned to her alma mater as the head coach of Trinity University’s tennis program.
The Junior Tennis + Golf Camp is held weekly during the summer, Monday through Thursday. Campers will receive tennis instruction by a USPTA or PTR Professional and golf instruction by a PGA Professional. These camps have a small student to teacher ratio and are a wonderful way for junior players to learn the rules and etiquette for golf and tennis.
Please contact our golf staff to book your Junior Tennis/Golf Camp at 434-325-8255
Daily Schedule:
9:00am – 11:00am Tennis
11:00am – 12:30pm Pool/Lunch (Lunch Included)
12:30pm – 2:30pm Golf
2026 Junior Camp Rates
Weekly: $399
Daily: $119
2026 Junior Camp Dates
June: 22-25; 30-July 2
July: 13-16; 27-30
Aug: 10-13
$252 per person
Friday: 3:00pm-5:00pm
Saturday: 11:00am-1:00pm
Sunday: 9:00am-11:00am
$336 per person
Friday 3:00pm-5:00pm
Saturday 11:00am-1:00pm + 3-5pm
Sunday 9:00am-11:00am
$420 per person
Friday 3:00-6:00pm
Saturday 11:00pm-1:00pm + 3:00pm-5:00pm
Sunday 9:00am-12:00pm
Customized schedules available
All levels will benefit from this program which includes: video analysis, snacks, academy souvenir, and 15% merchandise discount. Bring your own group and customize the academy to your needs! Great for USTA teams.
For registration or more information, please call 434-325-8345.
Monday-Saturday
1:00PM-2:30PM (Pickle Ball)
Friday
1:00PM-2:30PM (Pickle Ball)
2:30PM-4:00PM (Tennis)
Saturday
1:00PM-2:30PM (Pickle Ball)
2:30PM-4:00PM (Tennis)
Sunday
9:30AM-11:00AM (Pickle Ball)
11:00AM – 12:30PM (Tennis)
Complimentary for all Indoor Unlimited Wintergreen Club Members.
Wintergreen Resort Lodging Guests $12
Join us for Open Play Plus+ at Devils Knob
Racquet Sports. These open-play sessions will begin
with a brief instructional segment to enhance strategic
understanding and improve on-court execution.
Unlimited Club Members: $30
Club Members: $34
Wintergreen Resort Lodging Guests: $40
All levels and all ages welcome.
A video analysis of all strokes is a prerequisite for Juniors and preferred for Adults.
This clinic focuses on Fitness, Technique, Strategy, Point Play, Fundamentals.
Narrated slow motion analysis delivered as private YouTube link $175.
Unlimited Club Members: $60
Club Members: $68
Wintergreen Resort Lodging Guests $80
Unlimited Club Members: $60
Club Members: $68
Wintergreen Resort Lodging Guests $80
Program for Junior and Adult players, covers all aspects of player development and practicing to improve your game.
Technical analysis required.
Monday-Saturday
1:00PM-2:30PM (Pickle Ball)
Friday
1:00PM-2:30PM (Pickle Ball)
2:30PM-4:00PM (Tennis)
Saturday
1:00PM-2:30PM (Pickle Ball)
2:30PM-4:00PM (Tennis)
Sunday
9:30AM-11:00AM (Pickle Ball)
11:00AM – 12:30PM (Tennis)
Complimentary for all Indoor Unlimited Wintergreen Club Members.
Wintergreen Resort Lodging Guests $12
Join us for Open Play Plus+ at Devils Knob
Racquet Sports. These open-play sessions will begin
with a brief instructional segment to enhance strategic
understanding and improve on-court execution.
Unlimited Club Members: $30
Club Members: $34
Wintergreen Resort Lodging Guests: $40
All levels and all ages welcome.
A video analysis of all strokes is a prerequisite for Juniors and preferred for Adults.
This clinic focuses on Fitness, Technique, Strategy, Point Play, Fundamentals.
Narrated slow motion analysis delivered as private YouTube link $175.
Unlimited Club Members: $60
Club Members: $68
Wintergreen Resort Lodging Guests $80
Unlimited Club Members: $60
Club Members: $68
Wintergreen Resort Lodging Guests $80
Program for Junior and Adult players, covers all aspects of player development and practicing to improve your game.
Technical analysis required.
Please call 434-325-8235 for event updates or inquire at the Devils Knob Racquet Sports Pro Shop.
All Racquet Sports events will be held at Devils Knob Tennis except otherwise indicated.
View and book your lessons, clinics, and more with Court Reserve!
March 2026
14: St. Paddles Day Social, Devils Knob
April 2026
17: Spring Down to the Valley Mixer, Stoney Creek
24: Spring Up the Mountain Mixer, Devils Knob
May 2026
1-5: Cinco De Mayo Courtside Celebration, Devils Knob
15: Veritas Destination Event, Off-Site, Veritas Vineyards
22-24: Memorial Day Tournament, Devils Knob
24-25: WTG Paddle Battle, Devils Knob
June 2026
2-4: WTG Summer Swing – Grand Prix Series, Devils Knob
5-6: WTG Summer Swing – Grand Prix Series, Devils Knob
7: French Open Super Pro-Am, Devils Knob
8-11: Nike Wintergreen 10s Camp, Devils Knob
16-18: WTG Summer Swing – Grand Prix Series, Devils Knob
19-20: WTG Summer Swing – Grand Prix Series, Devils Knob
20: Summer Solstice Singles, Devils Knob
22-25: Junior Golf & Tennis Camp, Stoney Creek
24: Summer Nights Under the Lights, Devils Knob
29-July 2: Junior Golf & Tennis Camp, Stoney Creek
July 2026
4: July Jubilee Jam, Devils Knob
7-9: WTG Summer Swing – Grand Prix Series, Devils Knob
10-11: WTG Summer Swing – Grand Prix Series, Devils Knob
12: Royal White Wimbledon Event – Devils Knob
13-16: Junior Golf & Tennis Camp, Stoney Creek
20-23: Nike Wintergreen 10s Camp, Devils Knob
24-26: Racquet Wars at Wintergreen, Devils Knob
27-30: Junior Golf & Tennis Camp, Stoney Creek
August 2026
3-6: Junior Golf & Tennis Camp, Stoney Creek
10-13: Nike Wintergreen 10s Camp, Devils Knob
14-15: WTG Summer Swing – Grand Prix Series, Devils Knob
September 2026
5-6: Yard Sale Social/Labor Day Tournament, Devils Knob
11-13:US Open Box Seat Social, Devils Knob
October 2026
17: Oktoberfest Dinks and Drinks, Devils Knob
November 2026
27: Turkey Burning Fitness Event, Devils Knob
December 2026
15: Ugly Sweater Pro-Am, Devils Knob
19-22: Hittin’ in the Holidays Nike Challenger Camp
28-31: Hittin’ in the Holidays Nike Challenger Camp
Please call 434-325-8235 for event updates or inquire at the Devils Knob Racquet Sports Pro Shop.
View and book your lessons, clinics, and more with Court Reserve!
