If you’re wondering why people love living in Lake Oswego, September offers the perfect answer. Summer isn’t quite ready to let go, the farmers market is still in full swing, wine events return, community gatherings continue, and there’s no shortage of opportunities to learn something new, get outdoors, or connect with your community.

Whether you’re a longtime resident or thinking about making Lake Oswego home, here are some of the best events happening around town this September.

September 5 | Lake Oswego Farmers’ Market

The award-winning Lake Oswego Farmers’ Market is celebrating its 25th season, and September is one of the best times to visit. Shop fresh Oregon produce, artisan foods, baked goods, flowers, handcrafted gifts, and enjoy live music while the kids participate in the popular Farm Fresh Kids program.

Date: Saturdays throughout September (Sept. 5, 12, 19 & 26)

Time: 8:30 a.m. – 1:30 p.m.

Location: Millennium Plaza Park, 200 First Street

Cost: Free admission

September 5 | Southern Hemisphere Wine Flights at Zupan’s

Take your taste buds on an international journey without leaving Lake Oswego. This self-paced tasting features exceptional wines from Australia, New Zealand, and South Africa, making it a perfect afternoon stop for wine lovers.

Date: Saturday, September 5

Time: 1:00 – 3:00 p.m.

Location: Zupan’s Market, Lake Oswego 16380 Boones Ferry Rd.

Cost: $35 Tickets online

September 6 | Artist Talk with Susan Schenk

Meet local mixed-media artist Susan Schenk as she shares how she transforms vintage atlas pages into stunning dimensional artwork. Guests can even try the techniques themselves during this interactive presentation.

Date: Sunday, September 6

Time: 2:00 – 3:00 p.m.

Location: Lake Oswego Public Library, 706 Fourth Street

Cost: Free

September 8 | Pints from the Past

History buffs won’t want to miss this fascinating presentation on the legendary 1962 Columbus Day Storm, one of the Pacific Northwest’s most devastating weather events. Author and speaker Sig Unander brings local history vividly to life.

Date: Tuesday, September 8

Time: Doors open 6:30 p.m.; presentation begins at 7:00 p.m.

Location: To Be Announced

Cost: Free

September 10 | Long Shadows Wine Dinner

Enjoy an elegant multi-course dinner paired with acclaimed wines from Washington’s celebrated Long Shadows Winery. Seating is extremely limited, making this one of the month’s premier culinary experiences.

Date: Thursday, September 10

Time: 5:30 p.m.

Location: Zupan’s Floral Shop, 16380 Boones Ferry Rd.

Cost: $195 Tickets online

September 11 | You Can’t Take It With You

The Lakewood Center brings this 1936 Pulitzer Prize-winning comedy to the stage. Find out what happens when the lifestyles and philosophies of two sets of future in-laws collide.

Date: September 11 – October 18

Time: Wednesdays, Thursday, Fridays and Saturdayas at 730 p.m.; Sunday Matinees and Saturday matinees on September 16 and October 10 at 2:00 p.m. WOW night (Wine or Whiskey) on September 30th.

Location: Lakewood Center for the Arts, 368 S. State Street

Cost: $47/Adults; $30/Youth under 25

September 12 | Cannoli Second Saturday

Sometimes the simplest events are the sweetest. Stop by Zupan’s for freshly piped cannoli from Bella’s Italian Bakery—a delicious monthly tradition.

Date: Saturday, September 12

Time: 11:00 a.m.

Location: Zupan’s Market

Cost: $5

September 15 | The AI Toolkit Series

Curious about ChatGPT, Copilot, or other AI tools? This free hands-on class from the Lake Oswego Public Library is designed to help beginners understand artificial intelligence while learning how to use it safely and effectively. Titled, “Demystifying AI: Intro to AI (Part 1) Foundations for Everyday Use,” the class will repeat October 20. Participants are asked to bring smartphones, laptops or tablets with internet access.

Date: Tuesday, September 15

Time: 2:00 – 3:30 p.m.

Location: Lake Oswego Adult Community Center, 505 G Avenue

Cost: Free, but register by calling 503.635.3758

September 19 | Historic First Addition Walking Tour

Explore one of Lake Oswego’s most beloved neighborhoods with a guided walking tour through historic First Addition. Learn about the people, homes, and businesses that helped shape the original City of Oswego.

Date: Saturday, September 19

Time: 10:00 – 11:00 a.m.

Location: First Addition

Cost: $10 Members | $12 Non-members- Register online

September 24 | Live & Local at LORAC

Enjoy live music, local food, and a relaxed community atmosphere during the final Live & Local event of the season. Grab dinner from a food truck, sip a local beer or wine, and enjoy a beautiful September evening with neighbors.

Date: Thursday, September 24

Time: 4:00 – 8:00 p.m.

Location: Lake Oswego Recreation & Aquatic Center (LORAC),17525 Stafford Rd.

Cost: Free admission (food & beverages available for purchase)

September 24 | Emergency Preparedness Fair

National Preparedness Month is the perfect reminder to prepare for whatever comes our way. This family-friendly event includes emergency vehicles, live demonstrations, giveaways, preparedness workshops, children’s activities, and the opportunity to meet Lake Oswego’s first responders—including K9 Shadow.

Date: Thursday, September 24

Time: 4:00 – 6:00 p.m.

Location: Lake Oswego City Hall, 380 A Avenue

Cost: Free

September 26 | Creating Backyard Habitat Workshop

Want to make your yard more wildlife-friendly? Learn how to create native habitat that supports birds, pollinators, and other local wildlife while discovering the Backyard Habitat Certification Program.

Date: Saturday, September 26

Time: 9:00 – 11:00 a.m.

Location: Tryon Creek State Natural Area Classroom, 11321 SW Terwilliger Blvd.

Cost: Free (registration required)

September 29 | World Cinema Series: Panda Plan

Wrap up the month with an international film at Lake Theater & Café. This free screening of Panda Plan (presented in Mandarin with English subtitles) is followed by a community discussion.

Date: Tuesday, September 29

Time: 5:30 – 8:00 p.m.

Location: Lake Theater & Café, 106 N. State Street

Cost: Free (food and drink purchases encouraged)

There’s Always Something Happening in Lake Oswego

From farmers markets and wine tastings to neighborhood walks, educational programs, and family-friendly festivals, September is packed with opportunities to enjoy everything that makes Lake Oswego such a vibrant place to live. Whether you’re exploring a new hobby, supporting local businesses, or simply enjoying the changing seasons, these community events are a great reminder that life here extends far beyond beautiful homes—it’s about being part of a connected, active, and welcoming community.

If you’d like to explore being part of the Lake Oswego community, give us a call. We’d love to help make that happen!

Kevin Costello kevin.costello@cascadehasson.com 503.939.9801

Riley Costello riley.costello@cascadehasson.com 971.322.6205