Upcoming Events
Closed to the Public
Saturday March 14th
The Winery is closed to the public for our Spring Time Wine Club Member Release Party.
Wine Club Members watch for your email with more details of the upcoming release and event details.
Game Night – Trivia
Thursday, April 16th | 5-7pm
Game Night at Blakeslee Vineyard just leveled up!
Trade your usual after-work routine for an evening of wine, laughs, and a little friendly competition from 5–7 PM. Grab a glass (or split a bottle with friends), snack on delicious lite bites, and settle in for all the fun.
This April, we’re putting your knowledge to the test with Trivia: Are You Smarter Than a 5th Grader? Get ready for some throwback questions, big laughs, and prizes you’ll definitely want to take home.
Round up your crew, sip, play, and make it a night to remember—because everything’s more fun with a little wine involved.
Reservations are not required, but always a good idea!
Sip & Paint with Vine Gogh
Monday, April 20th | 5-8pm
Sip, swirl, and get a little artsy!
Grab your friends and join us for a laid-back Sip & Paint experience. We’ll provide everything you need-just bring your creativity (and maybe a love for wine). No talent necessary…just good vibes, great wine, and those unbeatable Mt Hood views.
Pre-registration is required. Purchase Here
Sips & Sounds with Rob Rainwater
Saturday, April 25th | 2-4:30pm
We’re thrilled to welcome local favorite Rob Rainwater, an Americana singer-songwriter inspired by the legends — the Pauls (Simon & McCartney), Bob Dylan, and Tom Petty. Expect soulful storytelling, catchy melodies, and the perfect soundtrack to your afternoon at the vineyard.
Bring your friends, grab a glass (or a bottle), and settle in for an afternoon that hits all the right notes and feels.
Reservations not required but encouraged.
Annual Kentucky Derby Party
Saturday, May 2nd | 12-5pm
Blakeslee Vineyard Estate presents our Annual Kentucky Derby Party — and trust us, this is one event you do not want to miss.
Dust off your boldest hats, sharpest suits, and most fabulous Derby looks… it’s time to show up in style.
Step into the excitement with live viewing and mock betting of vintage black & white Kentucky Derby races, bringing all the charm and thrill of Derby Day to life. Sip, socialize, and compete in a lineup of lively games while you go head-to-head for fabulous prizes.
Think you’ve got the look? We’ll be crowning Best Hat, Best Dressed Couple, and more — so bring your A-game.
Big energy, great wine, unforgettable moments… this is Derby Day, Blakeslee-style.
Tickets are $45 and include a glass of wine, food and fantastic fun, games and prizes.
Purchase HERE
A Roarin’ Good Time
November 28-30
12pm-5pm
Join us for an elite tasting flight of our Blanc de Blancs, Estate Reserve White Pinot Noir, Reserve Pinot Noir and Sheila Pinot Noir. All paired with Sheila’s famous chocolate chip cookies. Limited edition holiday wine packages will also be available!
No RSVP required, see you at the tasting room!
Aaron Meyers
Saturday, August 23rd
6pm to 8pm
The incredible Aaron Meyers will be returning again and this is absolutely another event you will NOT want to miss out on (along with some amazing wines!)
Romantic Winter Event
Take in the beauty of the setting with Aaron Meyer as he performs in our Piazza for a limited crowd. Get ready to enjoy some of your favorite tunes as you’ve never heard them before, fireside and intimate. Enjoy the spectacular wines and views of Blakeslee Vineyard paired with the signature sounds of Aaron Meyer.
- Open seating / first come, first served.
- 21+ event
- Tickets: $45 – limited quantity
- Purchase tickets: online (SOLD OUT)
- Tickets are Non-Refundable
Magic in the Mountains
Saturday, June 10th
1PM – 4PM
A Chehalem Mountains Wine Tasting
At the gateway to Oregon’s prestigious Willamette Valley wine growing region, just 35 minutes from Portland, you’ll discover wines produced by 30+ of Oregon’s most highly acclaimed wineries paired with food bites from incredible purveyors during a fun afternoon at the Allison Inn and Spa.
Holiday Closures
We are closed on these major US holidays:
Easter Sunday
Fourth of July
Thanksgiving
Christmas Eve & Day
New Years Eve & Day
Magic in the Mountains
Saturday, June 10th
1PM – 4PM
A Chehalem Mountains Wine Tasting
At the gateway to Oregon’s prestigious Willamette Valley wine growing region, just 35 minutes from Portland, you’ll discover wines produced by 30+ of Oregon’s most highly acclaimed wineries paired with food bites from incredible purveyors during a fun afternoon at the Allison Inn and Spa.