Willamette Valley Wine & Pickle

Overview

A seven-hour day custom-built around pickleball and wine, run for private groups of 6 to 16.

You spend it with Wes, a Pickleball Hall of Fame inductee, who runs a small-group clinic at a maximum 1:8 ratio. Players get sorted by level — 3.0, 3.5, 4.0 — so you’re matched with people who play like you. Larger groups get additional pros and coaches. Beyond the instruction, it’s a day of playing games and hearing stories from someone who did this at the highest level.

Then a curated luncheon built around your group’s tastes, with drinks. Then everyone caravans to a boutique Willamette Valley winery for a private tasting.

Everyone goes home with a swag bag.

Jessica runs it. She also owns The Painted Lady in Newberg, which is one of the best restaurants in the valley and tells you what to expect from the lunch. She’ll work around dietary needs if you email ahead, and she has insider pricing on lodging around the valley if you’re making a trip of it.

You can bring your own group or join one that’s forming.

If you’ve got a group of players coming to wine country, book this early. It runs on one pro’s calendar.

Common questions

How many people?
Six minimum, sixteen maximum. Private groups.

How long does it take?
Seven hours. Plan the whole day around it.

Who’s the pro?
Wes, a Pickleball Hall of Fame inductee. Larger groups get additional pros and coaches alongside him.

What if we’re different skill levels?
Players get grouped by level — 3.0, 3.5, 4.0 — so you’re playing with people at your standard.

What’s included?
Clinic and coaching, a curated luncheon with drinks, a private tasting at a boutique winery, and a swag bag.

Can I join if I don’t have a group?
Yes, you can join one that’s forming. Email Jessica.

Are dietary needs a problem?
No, but tell them in advance.

Can they help with lodging?
Yes, Jessica has insider pricing on accommodation around the valley.

How far ahead should I book?

Well ahead. It runs on one pro’s availability and the groups are small.

WVWP - Option 3