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Play Pickleball in the World’s #1 Wine Tasting Region, Oregon Wine Country.
[ About ]■
DINK, DRINK & DINE
We create unforgettable experiences that blend the thrill of pickleball with the refined pleasures of Willamette Valley’s world-class wines and culinary artistry.
2026 Dates
March 14 | April 11 | May 2 | June 20 | July 11 | August 22
Our Founders
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Wes Gabrielsen
Co-Founder & Coach
Wesley Gabrielsen’s pickleball journey started when he was a student in middle school and has evolved into him being one of the most decorated players in the history of professional pickleball. Gabrielsen has accumulated success in singles, doubles and mixed doubles. He is an 11-time USAPA National Champion, six-time Canadian National Champion, PPA Australia Champion, two-time Tournament of Champions Gold Medalist, and two-time U.S. Open Champion. Due to the accomplishments of his playing career, Wes was inducted into the 2022 Class of the Pickleball Hall of Fame. Gabrielsen also has over a decade of pickleball coaching experience and has served as the Head Coach of MLP’s Austin Pickleballers Club. In addition to his playing and coaching duties, he provides both one-on-one lessons and group clinics throughout the United States and internationally. Wes was raised in the beautiful Pacific Northwest, where he continues to live in the Willamette Valley area.
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Jessica Bagley
Co-Founder & Concierge
Jessica Bagley brings more than 25 years of experience in the hospitality industry. For over two decades she has owned and managed The Painted Lady Restaurant, a AAA 4-Star, Forbes 4-Diamond property, while living and raising her family here in the Willamette Valley.
Jessica first picked up a paddle in 2024 and it was passion at first play. Now she plays five days a week.
Jessica is always scouting for ways to introduce people to all that Willamette Valley has to offer and when she started taking lessons from Wes, it wasn’t long before an idea that had been percolating morphed into the Willamette Valley Wine & Pickle project.
Jessica’s passion and talent for hospitality and creating opportunities for locals and visitors alike to enjoy the beauty and bounty of the Willamette Valley, combined with Wes’ professional experience and accessible coaching style makes for a natural combination to curate a dynamic, memorable experience.
In a time when people are craving adventure and experiences more than things, Jessica and Wes combining both their expertise and passion for hospitality and the fastest growing sport in America seemed like a natural next step for the enterprising duo.
Willamette Valley Wine & Pickle invites people to come to this world renowned area to enjoy our world class wines, views, play pickleball with a pro and share a high end lunch with a personalized tasting experience just for your group. You can bring your own group together, or join a group of people who share similar interests.
[ OUR STORY ]
[ PACKAGES ]
This entire experience will be enjoyed with Wes, and for larger groups some other pro players/coaches. It’s an opportunity to receive elite coaching, play some fun pickleball games, listen to great pickleball stories, and to ultimately build a connection with a pro pickleball player throughout the day.
Small group instruction from a top professional pickleball player/coach and Pickleball Hall of Fame Inductee
1:8 ratio, maximum of pro instructor to group participants
3 hours of pickleball
2 hours of clinic starting at 9 a.m.
1 hour of Round Robin Play
Structured Feedback from Wes
Elevated luncheon tailored to the group’s palate accompanied with selection of beverages and libations.
After the clinic, the group will caravan to the chosen winery to have an intimate tasting experience from a local boutique Willamette Valley winery.
All guests will receive a parting gift/swag bag to commemorate this experience.
Please allow seven hours for this single day experience as you plan your trip. For additional trip support, contact Jessica.
More WVWP experience packages coming soon!
Book this experience>
Single Day Experience
LEVELS 3.0 | 3.5 | 4.0
Players will be grouped with other players of the same level.
2026 DATES
March 14, April 11, May 2, June 20, July 11 & August 22
[ FAQ ]Common Questions
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Reach out to our founder Jessica for special insider pricing on various lodging accommodations throughout the valley at wvwinepickle@gmail.com
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Please email or call with any dietary concerns. We will do our best to take dietary restrictions into consideration but we may not be able to accommodate all food allergies.
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Absolutely! Each event will be different. The lesson and luncheon are unique to the group and we will work with a handful of boutique wineries.
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Yes, you and/or group will need your own transportation.
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With a minimum of eight guests, we can create a special experience just for your group. We will incorporate either spirits, ales or a non-alcoholic experience based on the group’s preference.
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We always recommend bringing layers to Oregon Wine Country. Even in the summer times, our evenings can get chilly.
paddle
non-marking tennis/court shoes
protective eyewear (suggested)
water bottle
athletic wear
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We are flexible and available on other dates provided there is the equivalent of a party of 8 people booking the experience and Wes is not on tour.
[ ADDITIONAL INFORMATION ]