The first weeks of December 2026 are when Portland and Lake Oswego go fully festive, and nearly all of it sits an easy drive from 1111 SW Coronado St. The Christmas Ships return to the Willamette starting December 3, the Holiday Market opens at Pioneer Courthouse Square on December 4, and the big light festivals at The Grotto and Portland International Raceway run through the month. Every event below is confirmed for 2026, and together they make a strong argument for moving into a home like this one in time for the holidays.
3-20
Christmas Ships Parade on the Willamette & Columbia
Evenings from Thursday, December 3 | Portland & Vancouver waterfronts
About 80 illuminated boats make up the longest continuously running illuminated boat parade in the United States, and the 2026 season runs December 3-20. Early-December evenings include the combined fleet from the M. James Gleason Boat Ramp toward the Vancouver Waterfront on December 3 and the run into North Portland Harbor on December 4, with free viewing from the riverfronts. Dress warm, bring cocoa, and you can watch several nights without ever going far from SW Portland. The full fleet schedule is on the Christmas Ships parade schedule page.
4-23
Holiday Market at Pioneer Courthouse Square
Friday, December 4 through Wednesday, December 23 | 701 SW 6th Ave
Portland Saturday Market's downtown holiday pop-up brings more than 75 Pacific Northwest artisans under the square's lights for three weeks of seasonal shopping: ceramics, jewelry, textiles, and handmade gifts, all in the city's living room. It is a relaxed alternative to mall shopping and an easy lunch-hour or weekend stop. Details are on the Pioneer Courthouse Square events page and the Portland Farmers Market site.
Dec 30
The Grotto Christmas Festival of Lights
5:00 - 9:30 PM nightly | 8840 NE Skidmore St
A quarter-mile walk-through with millions of lights strung through the sanctuary's forest, with nightly choir performances in the Chapel of Mary, hot drinks, and holiday treats. It runs November 27 through December 30 (closed Christmas Day) and is one of Portland's most atmospheric holiday traditions. Tickets and the nightly choir schedule are on the Grotto Festival of Lights page.
Dec 31
Winter Wonderland at Portland International Raceway
Nightly, November 27 - December 31 | 1940 N Victory Blvd
More than a million lights line about two miles of drive-through holiday display, and 100 percent of the proceeds feed local families through the Oregon Food Bank and school programs. Early December brings special nights too: the Lights & Leashes dog walks on November 30 and December 1 let you walk the course with your dog, and Bike the Lights happens November 28. Full dates and tickets are on the Winter Wonderland Portland site and its Lights & Leashes page.
Lake Oswego Holiday Half, 15K, 10K & 5K
Sunday, December 13 | Lake Oswego
The Lake Oswego holiday race weekend lets you earn the season's indulgence: a holiday-themed half marathon, 15K, 10K, and 5K winding through the city's neighborhoods and waterfront on Sunday, December 13, 2026. It is about 10 minutes from SW Portland, and the festive, family-friendly energy is a fun way to see Lake Oswego at its most decorated. Registration opens through the City of Lake Oswego Parks & Recreation page.
11
Portland Holiday Brew Fest at Pioneer Courthouse Square
Friday, December 11, 5:30 - 10 PM | 701 SW 6th Ave
For grown-up holiday cheer, the Holiday Brew Fest takes over the square with winter ales and ciders from regional breweries under the tree lights. It is a short hop from the Holiday Market, so you can shop and then toast the season in one evening downtown. The square's December lineup is on the Pioneer Courthouse Square venue page.
The Weeks Before and After
December opens on the heels of a busy late-November run, and the weeks around it are already covered in our late-November guide (ZooLights from November 20, the tree lightings on November 27, and Small Business Saturday) and the broader November and December overview. Beyond early December, ZooLights runs through January 3 and the winter events guide carries the season into the new year.
A Cozy Season at the Forest Home
Tryon Creek State Natural Area, directly across the street from the property, keeps its family programs running through the season, including a Nature Walk & Storytime session on Water Cycle & Rain on Friday, December 11 on the Friends of Tryon Creek calendar. Back at 1111 SW Coronado St, the remodeled kitchen, two fireplaces, and covered deck were made for exactly this stretch of the year: a big table for the holidays, warm corners for quiet mornings, and a forest that glows in the low winter light. If you would like to see the property dressed for the season, or simply plan a December move, contact Danielle Bade to schedule a private tour.
Danielle Bade
Principal Real Estate Broker, Bade Real Estate