Lake Oswego Shines Bright for the Holidays: Events You Won’t Want to Miss

Lake Oswego always embraces the magic of the season, from sparkling lights along the lakefront to hometown traditions that bring neighbors together year after year. During the holidays, the city’s parks, galleries, and historic spaces turn into gathering spots where you can shop local, meet Santa, and soak up small‑town charm without ever leaving the metro area.

61st Annual Tree Lighting Festival

The season officially kicks off at the 61st Annual Tree Lighting Festival on Friday, November 28, 2025, from 3:00–7:00 PM at Millennium Plaza Park, with the tree lighting at 5:30 PM. Expect live music, a festive holiday marketplace, photos with Santa, and even reindeer viewing as the City of Lake Oswego and the Lake Oswego Chamber of Commerce light up downtown together.

Arts Council Holiday Marketplace

If you love gifting local, the Arts Council of Lake Oswego Holiday Marketplace at Artspace Gallery runs November 11–December 24 and features fine art, jewelry, ceramics, textiles, and other handmade pieces from regional artists. It is the perfect stop for one‑of‑a‑kind gifts, and you can make a whole afternoon of it by grabbing coffee downtown and strolling through Lake Oswego’s Gallery Without Walls.

Oswego Heritage Council Holiday Marketplace

On Wednesday, December 3, 2025, the Oswego Heritage Council Holiday Marketplace turns the historic Heritage House into a cozy holiday market from 12:00–5:00 PM, with Santa visiting from 3:00–5:00 PM. Shoppers can browse local, handmade goods while also supporting the Oswego Heritage Council, with food donations encouraged for the community food pantry.

Tinseltown Trolley

The Tinseltown Trolley is a beloved, family‑friendly holiday ride on the Willamette Shore Trolley, complete with decorations, carols, sweet treats, and a visit from a “very special guest” from the North Pole. Tickets typically go on sale in August and tend to sell out quickly, and 2025 rides are already listed on the activity calendar even though individual trips may show as full.​

As the lights go up and the calendars fill, here’s wishing you and your loved ones a season of cozy evenings, joyful gatherings, and Lake Oswego moments that feel straight out of a holiday movie. Whether you are sipping cocoa at Millennium Plaza Park, shopping local at a marketplace, or singing along on the trolley, may your holidays be merry, bright, and full of community spirit.