Upcoming Events

Memorial Day Weekend

May 22nd – May 25th | 11am-5pm

Join us for Memorial Weekend at Blakeslee Vineyard Estate, where exceptional wine meets breathtaking views of Mt. Hood. We’ll be open Thursday through Monday from 11am to 5pm, offering a full weekend of live music, relaxation, and celebration.

Enjoy performances from Scott Galegos (Saturday), Robert Tackett (Sunday), and Lew Jones (Monday), each playing from 1–4pm.

Whether you’re gathering with friends or hosting out-of-town guests, there’s no better place to spend the holiday weekend. Reservations are recommended.

Make Your Reservation

First Thursday live music with Simmer Down Duo

Thursday, May 7th | 5-7pm

It’s another fun First Thursday music night!

Molly Elkins and Craig Jahne are longtime friends and experienced musicians in the Portland area, playing in local bands Rock Doctors, Angela Haywood and Soul Expression, Probable Cause and The B4s. In 2015 we decided to branch off from our loud and rowdy rock ‘n roll background and simmer down a bit. And so the Simmer Down duo was formed. Start with a variety of popular folk, country, rock, pop selections then simmer them down to simple acoustic arrangements with vocal harmonies and the occasional looper to fill out the sound. Throw in the tackle box guitar that Craig made himself, and you have a fun and entertaining show!

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.

A Rare Taste of Blakeslee History Continues
May 30th-31st

In celebration of Oregon Wine Month, we’re unlocking the cellar once again and pouring some of our favorite Library Wines for you to enjoy.

May 30-31, alongside our Classic Wine Flight ($30), we’re offering a very exclusive, limited quantity, Premium Experience:

✨ Sheila Estate Reserve Pinot Noir Vertical Flight
Featuring vintages 2011, 2012, 2013, 2014 & 2015 — $50

This is a rare opportunity to explore how these wines have evolved over time—showcasing depth, elegance, and the unique character of each vintage.

And it gets even better…
All Library Wines from 2006–2016 are on sale throughout May! From 750ml bottles to impressive Magnums, 3L, and 5L formats, there’s something perfect for every table and every celebration.

Come sip, savor, and take home a piece of our story to share with the people who matter most.

Blakeslee Vineyard Estate Sherwood Oregon

Poolside Vineyard Sip & Paint with Vine Gogh
June 15th, 5:30-8pm

Grab your brushes and your best company — we’re heading poolside at the stunning Blakeslee Vineyard Estate in Sherwood for an evening of painting, sipping, and soaking in one of Oregon’s most beautiful settings.

Together we’ll paint Twilight Mountain — a breathtaking Mt. Hood scene inspired by the very view right in front of us. Watch the real mountain as you bring it to life on canvas. No experience needed, just a good attitude and maybe a glass of something wonderful.

We’ll be working with acrylic paint on an 11 × 14 canvas, and everything you need is included — paints, brushes, easel, and even an apron to keep you clean.

Your ticket includes painting instruction and all supplies.

Pre-purchased ticket required

Painting of a mountain in the background with billowy clouds in the sky and green trees and brush in the fore

Raise a glass to Dad this Father’s Day at Blakeslee Vineyard Estate! 🍷🍺

Join us Sunday, June 21st for a day full of great wine, cold beer, and friendly competition. All dads receive one complimentary beer or glass of wine on us—because they’ve earned it.

Plus, we’ll have Corn Hole Contests happening all day long—so bring your game face and let the fun begin!

Good vibes, beautiful views, and a little healthy competition…sounds like the perfect way to celebrate Dad.

Cheers to all the amazing fathers out there!

Patio Performance by Scott Gallegos
June 20th, 1-4pm

Scott Gallegos is an independent recording artist known for crafting emotionally driven music that blends modern production with authentic storytelling. His sound pulls from a mix of contemporary and classic influences, delivering tracks that are both relatable and sonically engaging. With a focus on honest lyrics and memorable melodies, Scott’s music connects with listeners through themes of life, growth, and personal experience.

Reservations not required but Recommended. Click HERE

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.

Purchase Tickets Here

Holiday Closures

We are closed on these major US holidays:
Easter Sunday
Fourth of July
Thanksgiving
Christmas Eve & Day
New Years Eve & Day

We want to help you celebrate mom for Mother’s Day at Blakeslee Vineyard Estate.

We have a special day planned which includes:
* Live music from 1-4pm by Rudolf Korv
* A new wine release &
* A carefully curated wine flight with mom in mind.
* Plus a special little something for mom to take home.

Our regular menu of Charcuterie, Hummus & Brie will be available for purchase along with our entire current wine releases.

Make Your Reservation Today!

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!)

Buy Tickets