Twenty years. One iconic Lucy moment. Zero shoes. Join us Saturday, October 10th as we celebrate two decades of Love & Squalor with Portland's first-ever grape stomp competition! Teams will battle it out barefoot in the barrels while we sip, snack, and cheer them on with wine, food trucks, live music, and games all afternoon. Squish season is coming — save the date.

If you want to read more about it, here’s a blog post

Here’s a news clip about the stomp!

Every Friday in October (10/2, 10/9, 10/16, 10/23, 10/30), we're transforming the winery bar into your new favorite Halloween hangout, complete with scary movies on the screen and candy pairings to match. Grab a glass of wine, settle in, and see what treats we've paired with tonight's fright. Show starts at 5pm, the bar is open 4pm-8pm

Sunday, October 4, 2026 | 5:45–7:00 PM tasting, followed by dinner

We’re heading out to Stoller for a special welcome tasting and dinner with the Wine & Spirits Guild of America (WSGA), bringing together more than 100 wine retailers from around the country. We’ll be pouring a few Love & Squalor favorites during the walk-around tasting, then sticking around for dinner and the chance to talk shop with some pretty serious wine buyers. It’s a great opportunity to get our wines in front of new markets, make some retail connections, and see where a little Oregon wine might travel next.

We're back aboard Island Style Charters' tiki boat for a Sips & Sights Tasting Cruise, and this round, we're the featured pour. Spend two hours cruising the Willamette River, around Ross Island and through downtown Portland — bridges, skyline, waterfront views, the whole tour — while we pour a flight of three Love & Squalor wines with a small snack on the side.

Not ready to stop there? The onboard bar stays open throughout with beer, cider, cocktails, and mocktails available for purchase.

Seats are limited and this cruise tends to sell out — reserve yours today.

All ages welcome. Alcoholic tastings and beverages available only to guests 21+ with valid ID.

📅 Sunday, October 4, 2026 | Check-in 1:30pm, cruise 2:00–4:00pm (2 hours)
📍 Departs from South Waterfront Park, 2001 S River Drive, Portland

We’re an official Scavenger Hunt spot for Dye Dye My Darling’s 6th Annual Halloween Monster Bash! The celebration features an entire day of live music, costumes, karaoke, local vendors, a neighborhood scavenger hunt, and Halloween mayhem - all while raising money for Iron Tribe Network. Learn all about the Monster Bash and how to participate here.

Looking for a fun way to kick off your weekend? Grab your yarn and join us for our monthly Stitch & Bitch! On the first Friday of every month, come to the tasting room for an evening of knitting, crocheting, and relaxing with a glass of wine. Whether you’re here to show off your skills or just untangle your week, this is the perfect spot to unwind. We’ll be pouring Love & Squalor wines to pair perfectly with your creativity and chatter.

Every Friday in October (10/2, 10/9, 10/16, 10/23, 10/30), we're transforming the winery bar into your new favorite Halloween hangout, complete with scary movies on the screen and candy pairings to match. Grab a glass of wine, settle in, and see what treats we've paired with tonight's fright. Show starts at 5pm, the bar is open 4pm-8pm

Join us at The Wedge, Oregon’s celebration of artisan cheese, wine, and all things delicious! We’ll be pouring Love & Squalor alongside an incredible lineup of Oregon cheesemakers and producers at Alder Block in SE Portland. Come taste, sip, shop, and discover some of the best local cheese and wine Oregon has to offer. 21+ only.

Alder Block (home of the Portland Night Market)
100 SE Alder Street
Portland, OR 97214

Tickets are $25 in advance and include cheese, food, and non-alcoholic beverage samples plus a $5 voucher to spend on cheese! An alcoholic beverages add-on (wine/cider/beer/spirits) is $15 and includes a commemorative tasting glass. At-the-door admission is $30 for food and $20 for beverages.

Early VIP entry (10:30am) is $75 and includes a goodie bag and two $5 cheese vouchers.

Join us for Hand Sew Happy Hour in collaboration with the Portland Modern Quilt Guild. Bring your hand-sewing projects, sip some wine, and connect with fellow makers. We gather on the last Friday of every month.

No RSVP needed — just come hang out!

Love to read? Hate the pressure of having to talk about what you’re reading? This is the book club for you. Bring whatever book you’re currently into, grab a glass of wine and some complimentary snacks, and settle in for about 90 minutes of quiet reading. No assigned book, no required discussion, no homework—just good books, good wine, and good company. Stick around and mingle afterward if you feel like it!

Looking for a fun way to kick off your weekend? Grab your yarn and join us for our monthly Stitch & Bitch! On the first Friday of every month, come to the tasting room for an evening of knitting, crocheting, and relaxing with a glass of wine. Whether you’re here to show off your skills or just untangle your week, this is the perfect spot to unwind. We’ll be pouring Love & Squalor wines to pair perfectly with your creativity and chatter.

Join us for Hand Sew Happy Hour in collaboration with the Portland Modern Quilt Guild. Bring your hand-sewing projects, sip some wine, and connect with fellow makers. We gather on the last Friday of every month.

No RSVP needed — just come hang out!

Hosted by Bird Bam Beth, this class will give you the skills you need to start playing American Mahjong. Here’s what you’ll learn:

Part 1 - August 13

• Rules Overview: Learn the game's official rules set by the National Mah Jongg League

• The Charleston: Practice The Charleston, the tile-swap ritual that starts every game

• Beginner Play: Play 1–2 hands using a beginner-friendly version of a simplified card

• Take-Home Materials: Go home with the beginner card and a cheat sheet to help you practice

Part 2 - August 20

• Rules Review: Brush up on the card and rules set by the National Mah Jongg League

• Basic Strategy: Introduce essential strategies and defensive thinking to your game

• Building Walls & Dealing: Learn how to build your wall and start dealing tiles the official way

• Guided Play: Play two full games, with real-time coaching and guidance

Cost: $120 for both sessions

Learn more and purchase tickets here.

Trashy Book Club meets every other month on the third Thursday, 5:30–7 pm (we're open until 8 if you want to linger). We read bold, romantic, gloriously over-the-top books and talk about them loudly, with wine in hand. Free to attend, no RSVP required. Order by the glass or try our rotating weekly flight, grab some snacks, and settle in. Come as you are — even if work runs a little late.

Up next:

- August 20th — The Song of Achilles by Madeline Miller

Read more about this event here

Trade the tasting room for the top deck. We're teaming up with Island Style Charters — home to Portland's first (and only!) tiki boat — for an evening cruise up the Willamette River to Willamette Falls, pouring a flight of Love & Squalor wines along the way.

On the ride up, Matt will walk you through our wines and the stories behind them — from Willamette Valley vineyard to bottle. On the return, kick back with a glass or bottle, take in live narration and river views, and watch the city lights come up as the sun goes down.

Expect tropical cocktails, onboard games, a little Portland history, and a full flight of our wines — all with unbeatable views of the falls and the river you won't get anywhere else.

Seats are limited and this cruise tends to sell out — reserve yours today.

This is an all-ages cruise. Wine tasting included with your ticket.

📅 Wednesday, August 19, 2026 | 5:30pm–8:30pm (approx. 3 hours)
📍 Departs from South Waterfront Park, 2001 S River Drive, Portland

Hosted by Bird Bam Beth, this class will give you the skills you need to start playing American Mahjong. Here’s what you’ll learn:

Part 1 - August 13

• Rules Overview: Learn the game's official rules set by the National Mah Jongg League

• The Charleston: Practice The Charleston, the tile-swap ritual that starts every game

• Beginner Play: Play 1–2 hands using a beginner-friendly version of a simplified card

• Take-Home Materials: Go home with the beginner card and a cheat sheet to help you practice

Part 2 - August 20

• Rules Review: Brush up on the card and rules set by the National Mah Jongg League

• Basic Strategy: Introduce essential strategies and defensive thinking to your game

• Building Walls & Dealing: Learn how to build your wall and start dealing tiles the official way

• Guided Play: Play two full games, with real-time coaching and guidance

Cost: $120 for both sessions

Learn more and purchase tickets here.

Looking for a fun way to kick off your weekend? Grab your yarn and join us for our monthly Stitch & Bitch! On the first Friday of every month, come to the tasting room for an evening of knitting, crocheting, and relaxing with a glass of wine. Whether you’re here to show off your skills or just untangle your week, this is the perfect spot to unwind. We’ll be pouring Love & Squalor wines to pair perfectly with your creativity and chatter.

Don your brightest pink and join us in the Valley for the 13th Annual Drink Pink Rosé Festival. Enjoy dozens of rosé and sparkling rosé selections, as well as a costume contest, photo booth, DJ, and local artisan and food vendors.

This is a 2-day event — Saturday, August 1 and Sunday, August 2. Each day features a different lineup of participating wineries. We will be there on Sunday!

Single-day admission is $55, while a two-day pass is available for $100. Admission includes a commemorative wine glass, unlimited tastings from participating wineries, entertainment, and access to local vendors. Food will be available for purchase onsite.

Join us on at Portland Wine Company for an after-hours celebration of the summer solstice. We're keeping the tasting room open late with a DJ, pizza, and of course plenty of wine to fuel the longest day of the year. Expect back-vintage pours, cellar door specials, and the perfect amount of Midsummer -- or Midsommar -- weirdness. 

In the industry or have a cellar you want to show off? Bring a bottle to share and get 30% off all bottle purchases. Extra points if you come dressed as Puck or the May Queen!

Whether you're a wine professional or just love a good late-night pour, come celebrate the solstice with exceptional wines and good company.

Friday, July 25th | 8 pm - 12 am | $10 advance purchase | Free for industry and wine club
**Tickets are $20 at the door, so buy yours in advance for the best price.**

Join us for Hand Sew Happy Hour in collaboration with the Portland Modern Quilt Guild. Bring your hand-sewing projects, sip some wine, and connect with fellow makers. We gather on the last Friday of every month.

No RSVP needed — just come hang out!

For the next Spin the Bottle, we’re excited to welcome Vincent Wine Company. Founded by winemaker Vincent Fritzsche, Vincent is known for thoughtful, minimal-intervention wines that showcase the character of Oregon vineyards with precision and restraint. We’re thrilled to share these distinctive wines with you and introduce (or reintroduce) one of the Willamette Valley’s most respected producers. Read more about them here.

As always, it’s a free tasting with no RSVP necessary.

We’ll be cleaning out a reflecting pool for the Semiquincentennia so have to close for the day! Enjoy those hotdogs and see you tomorrow.

Looking for a fun way to kick off your weekend? Grab your yarn and join us for our monthly Stitch & Bitch! On the first Friday of every month, come to the tasting room for an evening of knitting, crocheting, and relaxing with a glass of wine. Whether you’re here to show off your skills or just untangle your week, this is the perfect spot to unwind. We’ll be pouring Love & Squalor wines to pair perfectly with your creativity and chatter.

Join us for Hand Sew Happy Hour in collaboration with the Portland Modern Quilt Guild. Bring your hand-sewing projects, sip some wine, and connect with fellow makers. We gather on the last Friday of every month.

No RSVP needed — just come hang out!

POUR SOME LOVE: Blending Event

Join winemaker Matt, assistant winemaker Alana, and tasting room manager Jess for a hands-on blending event built around our barrelled Gamay Noirs. Taste through individual components, experiment with different blends, and discover how small adjustments can completely transform a wine. Includes tastings, light snacks, 10% off bottles, and a $5 coupon toward your future 2025 L&S Gamay Noir purchase.

$45 General / $25 Club Members | Limited to 20 People

Read more about it here