Decemberville Runs a Full Month This Year, and the Windows Carry It

Last December, the Sellwood Moreland Business Alliance billed its holiday program as "15 Days of Decemberville." Voting in the window contest closed December 13. This year, Decemberville '26 starts on Saturday, November 28, two days after Thanksgiving, and runs through December 31. That's 34 days, more than twice as long as last year.

What runs through all 34 days is the window displays, which stay lit along SE 13th Avenue, SE Milwaukie Avenue and SE Bybee Boulevard for the whole month. The ticketed and one-day events fall at the beginning and the end. Once you know where the windows are and which dates fall in that stretch, you can plan around them.

Last year's 44 windows, by street

The 2025 Winter Window Walk was the first one, and the alliance's list of entrants runs to business number 44. Grouped by street, the list shows how the walk covers the neighborhood:

Almost all of the windows sit on the two north-south shopping streets, and Bybee Boulevard links them. Last year's four winners came from all three. Luna Karina Masaya at 7044 SE Milwaukie Ave took Best in Show, and Adored Vintage at 7013 SE Milwaukie Ave won Most Aesthetic. Kim's Taekwondo at 8113 SE 13th Ave won Spirit of Sellwood, and The Focacceria at 1613 SE Bybee Blvd won Best Theme.

Businesses had until November 1 to sign up for the 2026 competition, which the alliance calls Window Wonderland. Most windows on Milwaukie, 13th and Bybee are probably the safe bet, but the 2026 map will have the final list.

What the extra weeks do to the window hunt

In 2025, the walk was a voting contest. Visitors scanned QR codes in each window, picked favorites in four categories, and could enter a prize drawing by leaving an email address. The 2026 version adds a game for families. The alliance's Decemberville committee gives each participating business one small letter to hide in its display, next to the voting QR code. Visitors find the letters on a printed map, put them together into a secret holiday phrase, and bring the finished map to one of several Holiday Hubs for prizes.

The longer season changes how you can play. Last year's 44 stops had to fit into about two weeks of voting. With 34 days, a family can do the 13th Avenue windows one weekend, the Milwaukie Avenue windows another, and pick up the Bybee stops on a coffee run to Fetch or a lunch at The Focacceria. The map and the letters stay up for the whole month.

Businesses have until November 13 to send the alliance their holiday events, such as markets, live music and performances, along with ongoing deals like food and drink specials, free gift wrap and month-long sales. The alliance plans to run all of it from one calendar on the Decemberville '26 page and to promote it with posters, table toppers and print ads around the city. For the full season, check that page as it fills in.

The dated events at the start and end of the month

The window hunt runs every day. These one-day and ticketed events already have dates. Several of them come before November 28, and most of the rest fall in the last two weeks of December.

1. Friday, November 13, 10:30 to 11:15 a.m. Red Yarn plays a children's concert at Sellwood Community House. Tickets are $15, or $13 for siblings, at the door, according to The Bee's events listing.
2. Friday, November 13, 7 to 8:30 p.m. Nate Query plays the Sellwood Sessions concert at Oaks Pioneer Church. The series raises money for the free summer concerts at Sellwood Park, and tickets cost $45 to $65.
3. Saturday and Sunday, November 14 and 15. St. Agatha's Parish Hall at 7959 SE 15th Ave holds its annual Christmas Bazaar, 9 a.m. to 4 p.m. on Saturday and 9 a.m. to 2 p.m. on Sunday. The Bee lists local vendors, homemade lunch, arts and crafts, and baked goods.
4. Saturday, November 28. Decemberville '26 and the Window Wonderland displays begin.
5. Sunday, December 6, 10 a.m. and 1:30 p.m. Sellwood Community House holds its Nutcracker Tea Parties, with tea, sweets and savories while Classical Ballet Academy dancers perform scenes from the Nutcracker. The online ticket page shows sales as closed.
6. Through December 15. For the Great Toy Drive with KGW, the Oaks Park Roller Rink gives $3 off on-site admission to anyone who brings a new, unwrapped toy worth $10 or more to any skating session. Each donation covers up to six discounted admissions.
7. Saturday, December 19, 10 a.m. to 3 p.m. The Sellwood Community House Decemberville Holiday Market at 1436 SE Spokane St brings in local makers and vendors, a hot cocoa bar and a bake sale. The house planned it to go with the neighborhood's Decemberville events.
8. Sunday, December 20, 5 to 9:30 p.m. At the Charlie FM Christmas Skate, 97.1 Charlie FM plays holiday music from 5 to 7 p.m. Photos with The Skating Santa and Chipper the Squirrel, a Christmas music trivia contest and a themed café menu run through the evening, and the rink's live pipe organ takes over from 7 to 9:30.
9. Monday, December 28, 7 to 10 p.m. Oaks Park holds an '80s aerobics-themed skate for ages 21 and up. The $24 admission includes one adult beverage.
10. Thursday, December 31, 7 p.m. to 1 a.m. The all-ages New Year's Eve skate party has a live DJ, party favors, prize drawings and a countdown to midnight. Skating costs $27, or $32 with champagne for guests 21 and up, and spectator tickets are $9.50, or $14 with champagne. Decemberville ends the same night.

The rink is at 7805 SE Oaks Park Way, and Oaks Park charges $4 per vehicle per day for parking. Its event listings and current prices are on the Oaks Park specials page.

With these dates in mind, December 19 and 20 is the busiest weekend of the season. The Spokane Street market fills Saturday, the Christmas skate fills Sunday evening, and the windows are open all weekend. A household that wants the whole thing in one trip can walk the 13th Avenue windows before the market, then head down to the rink the next night.

The Moreland Theater block on Milwaukie

The stretch of SE Milwaukie Avenue just south of the Moreland Theater has changed this year. The Bee reported in September that Monty's Red Sauce had recently opened in the space just south of the theater. The new Silly Daisy store sits south of Monty's, and a banner in the long-running Stickers restaurant space announces a Mexican restaurant to come.

Monty's Red Sauce is at 6716 SE Milwaukie Ave. KOIN's Everyday Northwest describes it as hearty, home-cooked Italian food from the team behind Montelupo in Northwest Portland, with Tyler Weeks as executive chef. Silly Daisy is at 6802 SE Milwaukie Ave. It carries children's clothing and accessories, baby goods, toys, women's clothing, jewelry, home goods and stationery, which fits the gift-shopping errand that the window hunt already puts on most families' list. Both businesses were on last year's window walk list.

On the other side of the theater, The Bee reported that the Limelight Bar and Restaurant still has most of its sidewalk seating, first put in during the pandemic, and that it fills every night. For a Westmoreland window loop, that puts dinner, a children's shop and a theater marquee on one block, about midway along the 16 Milwaukie Avenue stops from last year. Luna Karina Masaya and Adored Vintage, last year's Best in Show and Most Aesthetic winners, are a few blocks south, in the 7000 block.

Where to find the 2026 map

The alliance plans to put the event calendar, the specials and the Window Wonderland voting on its Decemberville '26 page. Last year, the printed window maps were free at every participating business while supplies lasted. Holiday Hubs are where finished scavenger maps get turned in for prizes. Any participating storefront on 13th, Milwaukie or Bybee should be a good place to pick up a map once the displays go up on November 28.

At Green Buck Real Estate, we see how much a neighborhood's walkable shopping streets add to everyday life in Sellwood-Moreland. If you own a home within walking distance of these windows and want to know what it's worth this season, request a free home valuation and we'll put together a report based on your street.