It’s wine harvest season—but lucky for us, there’s no need to travel far to celebrate. Lake Oswego’s 11th Annual Wine Walk is set for Saturday, October 4, and this year promises to be the biggest yet. With over 35 walkable downtown businesses and more than 70 wines to sip and sample, the streets of LO are turning into a wine lover’s dream.

Here’s your step-by-step game plan to make the most of it:

1. Buy your tickets early.

This event sells out every year, and for good reason. Tickets include twelve 1-oz wine pours, small bites, a custom LO Wine Walk glass (with its own lanyard “hammock”), and a reusable event tote with a tasting map and more. Click here for tickets.

2. Make a day of it.

Kick things off with the Lake Oswego Farmers’ Market in Millennium Plaza—October 4 is its final day of the season! Grab lunch at one of our downtown restaurants, do a little browsing or shopping, and be ready to raise your glass when the Wine Walk kicks off at 1:00 p.m.

3. Check-in early.

Check-in opens at 12:00 noon with wine tasting starting at 1:00 p.m. An early check-in gives you time to enjoy lunch, plan your tasting route, and take advantage of some crowd-free moments before the sipping begins.

4. Plan your path.

This year, more than 35 local businesses are hosting wine stations. From art galleries to skincare boutiques to real estate offices, the list is a “Who’s Who” of downtown LO—including favorites like Domaine Serene Wine Lounge, glassybaby, Lola’s Café Bar, Wizer’s Fine Wine, City Home, Wishbone Home & Design, R. Bloom’s, StretchLab, Meraki Medical Aesthetics and our own Cascade Hasson Sotheby’s International Realty.

With over 70 wines to choose from, you’ll want to map out your favorites first—just in case something runs out later in the day.

5. Dress for the weather.

October in Oregon is unpredictable. We’ve had Wine Walks in glorious sunshine and ones with a few sprinkles, so check the forecast and dress in layers. Comfortable walking shoes are a must—and don’t forget a tote bag for any goodies or wine you purchase along the way.

6. Hydrate.

Yes, the wine is delicious. But water is your best friend during this four-hour stroll. Be sure to stop for water now and then—you’ll thank yourself the next day.

7. Try something new.

One of the best things about this event is that it encourages exploration. Try wines you’ve never heard of. Walk into shops you’ve passed but never entered. The Wine Walk makes it easy to discover new favorites—both in the glass and on the map.

8. Take photos.

Document your day! 📸 Snap pics of wines you loved, places you visited, and good times with friends. You’ll want a record of the labels you liked for your next wine run—and you’ll be glad to have memories of a very Lake Oswego kind of afternoon.

Whether you’re a returning regular or first-timer, the 2025 LO Wine Walk is a community event you don’t want to miss. See you downtown on Saturday, October 4, with glass in hand!

Don’t miss out on a reason to Love Lake Oswego. Click the “Sign me up” button in the top right-hand column and receive weekly updates to our blog. And if you’re in the market for a house where you can drink all that wine, give one of us a call. We’d love to help make your next move your best one!

Kevin Costello kevin.costello@cascadehasson.com 503.939.9801

Riley Costello riley.costello@cascadehasson.com 971.322.6205