October in Lake Oswego is when fall really starts to settle in—and there’s no shortage of ways to get out and enjoy it. From theater and farmers’ markets to community events, family Halloween fun, and even a little wine tasting, here are some of the best things happening in and around Lake Oswego this October.
📚 Freedom to Read Month: The Perks of Being a Wallflower Book Giveaway
Thursday, October 1
Time: Starting when the library opens
Location: Lake Oswego Public Library, 706 Fourth Street
Cost: Free
Celebrate your freedom to read with a free copy of The Perks of Being a Wallflower by Stephen Chbosky. The Lake Oswego Public Library is giving away copies of the coming-of-age novel, which follows Charlie, a shy and sensitive high school freshman navigating friendship, family, trauma, love and growing up. The book has frequently been challenged or banned because of its frank treatment of sexual content, drug and alcohol use, sexual abuse, mental health, suicide and LGBTQ+ themes. Copies will be available at the library’s second-floor reference desk beginning October 1, while supplies last.
🎭 You Can’t Take It With You
October 1–18
Wednesdays, Thursdays, Fridays & Saturdays: 7:30 p.m.
Sunday matinees & Saturday, October 10: 2:00 p.m.
Location: Lakewood Center for the Arts, 368 S. State St.
Cost: Adults $47 | Youth under 25 $30
Online tickets: Additional $3 service fee
Looking for a night at the theater? You Can’t Take It With You is a 1936 Pulitzer Prize-winning comedy about two families whose very different lifestyles collide when Alice Sycamore invites her fiancé’s wealthy, buttoned-up parents to dinner. The result is a hilarious clash between the eccentric, free-spirited Sycamores and the proper Kirbys. It’s a classic comedy with plenty of heart—and a great excuse for a night out in downtown Lake Oswego.
🥕 Lake Oswego Farmers’ Market
Saturday, October 3
8:30 a.m.–1:30 p.m.
Location: Millennium Plaza Park, 200 1st Street
Cost: Free admission
The Lake Oswego Farmers’ Market is celebrating its 25th anniversary this year, and October is the perfect time to take advantage of the market’s final weeks of the season. Browse fresh produce, meats, seafood, cheeses, baked goods, jams, prepared foods, flowers, artisan products and more. Live music runs from 10:30 a.m.–12:30 p.m., and families can take part in the Farm Fresh Kids Program. There’s also a SNAP matching program of up to $20 each week.
The 2026 market runs Saturdays through October 31, so don’t miss your last chance to stock up on all those fall favorites.
♻️ Bulky Waste & Mattress Recycling Event
Saturday, October 3
9:00 a.m.–1:00 p.m.
Location: Republic Services, 10295 SW Ridder Road, Wilsonville
Cost: Free for Lake Oswego residents
Have a garage, basement or spare room that needs a fall clean-out? The City of Lake Oswego and Republic Services are hosting a free bulky waste and mattress recycling drop-off for Lake Oswego residents.
Accepted items include large household items such as furniture, appliances, scrap metal, clean untreated wood, certain gas-powered equipment, mattresses and several specialty recyclable materials. There are restrictions, so check the City’s guidelines before loading up the car. This event is for Lake Oswego residents only, and participants must be able to unload their items without staff assistance. For questions about accepted materials, contact Travis Comfort at 503.826.3897.
🍎 Lake Grove Sunday Market
Sunday, October 4
11:00 a.m.–2:30 p.m.
Location: Hallmark Drive near Mercato Grove
Cost: Free
The Lake Grove Sunday Market gets into the fall spirit with its “Back to School Block Party.” Come browse fresh, sustainable goods, listen to live music and let the kids participate in Farm Fresh Kids activities. It’s a great way to spend a Sunday afternoon supporting local vendors while enjoying one of Lake Oswego’s favorite community gathering spots.
🍷 Lake Oswego Wine Walk
Date: Saturday, October 3 from 1:00 p.m. to 5:00 p.m
Location: Downtown Lake Oswego
Cost: $60
Wine lovers, this one’s for you. The annual Lake Oswego Wine Walk brings more than 35 walkable downtown businesses together, with more than 70 wines available to sample throughout the event.
A $60 ticket includes 12 one-ounce wine pours, small bites, a custom Lake Oswego Wine Walk glass and a reusable tote bag with a tasting map. It’s a fun way to explore downtown businesses while discovering some new favorite wines—and because the event typically sells out, you’ll want to check online for availability and event details.
✉️ Freedom to Read Month: Dear Friend Creative Letter Writing
Sunday, October 11
2:00–4:00 p.m.
Location: Lake Oswego Public Library
Cost: Check with the library for details
Slow down and put pen to paper at this creative letter-writing event celebrating Freedom to Read Month. It’s an opportunity to step away from the digital world and enjoy the simple art of writing a thoughtful letter to someone you care about. Whether you’re an experienced letter writer or can’t remember the last time you actually mailed one, this is a fun, creative way to connect.
💊 Fall Drug Take Back Event
Saturday, October 24
10:00 a.m.–2:00 p.m.
Location: Mary’s Woods, Gallagher Building, 17550 Provost Street, Lake Oswego
Cost: Free
October is a good time to clean out more than just the garage. The City of Lake Oswego’s one-day drug take-back event provides a safe and convenient way for residents to dispose of unwanted or expired medications.
The drive-through event accepts prescription and over-the-counter medications, unknown medicines, veterinary medications and vape pens or e-cigarettes without batteries. Vitamins, empty pill bottles, medical waste and medications from businesses or institutions are not accepted. For liquids, gels or creams, place containers in a sealed plastic bag to prevent leaks. For more information contact Bonnie Hirhberger at 503.675.3992.
🎃 Monster Mash Spooktacular
Saturday, October 31
2:00–5:30 p.m.
Location: Christ Church Parish, 1060 Chandler Road
Cost: Check with event organizers
End the month with a little Halloween magic at the Monster Mash Spooktacular. Designed for children ages 0–12, this family-friendly afternoon features trick-or-treat streets where kids can collect sweets, toys and trinkets, along with spooky music and ghostly crafts. Costumes are encouraged, of course!
It’s a fun, low-key way for Lake Oswego families to celebrate Halloween together—and a perfect way to wrap up a busy month around town.
🍂 Fall Is a Great Time to Be in Lake Oswego
One of the things that makes Lake Oswego such a special place to live is that community life doesn’t slow down when summer ends. In fact, October brings its own rhythm: farmers’ markets, theater, neighborhood gatherings, creative events, family activities and plenty of opportunities to get out and connect with the people who make this community feel like home.
If you’d like to learn more about Lake Oswego subscribe to our blog and/or give us a call. We’d love to answer your questions and show you around.
Kevin Costello kevin.costello@cascadehasson.com 503.939.9801
Riley Costello riley.costello@cascadehasson.com 971.322.6205
