The Sherwood Saturday Market runs May through September, 9 a.m. to 1 p.m., in Cannery Square next to the library. It has no winter edition. For years that gave Old Town's calendar a clear shape: a busy summer, then a long quiet stretch broken up by the holiday parade.
This year, a walk-in wine tasting room that opened this summer keeps Friday-through-Sunday hours with no seasonal end date. The food cart pod proposed for the old white church was designed around Oregon's wet months. And December now has two evenings downtown, four days apart. Taken together, the newest pieces of Old Town are being built for November through April.
Mark these dates
- Nov. 7 through 15: CYT Portland Presents The Little Mermaid at Sherwood Center for the Arts
- Nov. 19 and 20: Cascade School of Performing Arts presents Disney's Frozen Jr.
- Tuesday, Dec. 1, 5 to 8 p.m.: Old Town Sherwood Winter Art Walk and Holiday Market
- Saturday, Dec. 5: Mosaic Arts Loft's Heritage Holiday Market from noon, holiday parade at 4 p.m., tree lighting around 5 to 5:15 p.m.
- Dec. 14: Last day of the Four Eights gallery exhibit at the Center
The rest of this post covers what's behind those dates and what has changed downtown since last year's tree lighting.
One room on First Street, two schedules
Olea Vineyards, a family-owned winery founded in 2013, held a ribbon cutting at 16017 S.W. First St. on July 8 for a walk-in tasting room. It shares the space with Mosaic Arts Loft, according to the Sherwood Sun. Olea's original tasting room on Parrett Mountain is becoming a members-only lounge and special-events venue. That leaves the Old Town room as the walk-in option, and no reservation is required.
The posted hours are Fridays 3 to 7 p.m., Saturdays noon to 6 p.m., and Sundays noon to 5 p.m. According to the Sun, the sparkling rosé, big reds and estate pinot are the most popular pours.
The shared room works because the two tenants use it at different times. Owner Tom Melillo explained the arrangement to the Sherwood Sun:
"The nice thing is when we're here, they're usually not, and when they have their classes in session, we're not."
Splitting the week like this means a room that one business might fill only a few days a week is in use for more of it. It also means the room is open to the public on weekends whatever the weather, and Saturday afternoon is exactly when the outdoor market used to bring people downtown in summer. In the same Sun story, Sherwood Area Chamber of Commerce executive director Dave Murray called the opening "a delight and a pleasure."
Saturday, Dec. 5, in order
The arrangement on First Street matters most on the first Saturday in December, when the room's art side and the street outside both have something going on. Here is how the afternoon lines up from the event listings:
- Noon: Mosaic Arts Loft opens its 2026 Heritage Holiday Market at 16017 S.W. First St. It features local artisans, original artwork, prints, handmade tree ornaments, holiday cards and home décor, plus pottery from the Ann Brucker Collection. Olea's regular Saturday hours also begin at noon.
- 4 p.m.: The Sherwood Holiday Festival parade starts near 12th Street and Sherwood Boulevard and ends at Cannery Square Park. The Robin Hood Festival Association lists the Sherwood High School Marching Band, the Maid Marian Court and Santa among the entries. Mosaic's listing tells shoppers to step outside between 4:00 and 4:30 p.m. to see it pass along Sherwood Boulevard and Pine Street.
- Around 5 to 5:15 p.m.: The tree lighting in Cannery Square Park, with several local school choirs and a sing-along led by the Junior and Senior Maid Marian Court.
- Through the evening at Cannery Square: A Santa tent with free surprise bags for kids, free hot dogs and cookies served with help from the Boy Scouts, and free hot chocolate and coffee, all while supplies last. The association's booth sells festival shirts.
Mosaic's page lists two closing times for its market. The description says 5 p.m. and the event details say 6 p.m., so confirm with Mosaic Arts Loft if you plan to shop after the tree lighting. The parade is run by an all-volunteer nonprofit, and it has a sign-up page for anyone who wants to help on the day.
Four days earlier, a Tuesday night
The parade is the long-running tradition. The Winter Art Walk adds a second evening downtown in the same week, and it runs on a weeknight. Sherwood Center for the Arts schedules the Art Walk twice a year. This year's dates are Tuesday, June 9, and Tuesday, Dec. 1, both 5 to 8 p.m., with the December edition doubling as a holiday market.
The Center's Art Walk page explains how it works. Pick up a map at the Center or at any numbered sandwich board in Old Town, then work through the stops in the six-block downtown area. At each stop, engage with the business to get a stamp. A map stamped at every stop goes back to the Center for a chance at a prize basket. Stops can include local art, artist conversations, hands-on activities, performances, and food and drinks. For the December list of participating businesses, the Center's event page says "More information to come."
A caption on Mosaic Arts Loft's site mentions an Art Walk on Dec. 2. The Center runs the event, and it lists Tuesday, Dec. 1.
Filling November at the Center
Before either December evening, the Center's calendar covers most of November. CYT Portland Presents The Little Mermaid has performances at 1 and 7 p.m. on Nov. 7, 3 p.m. on Nov. 8, 7 p.m. on Nov. 13, 1 and 7 p.m. on Nov. 14, and 3 p.m. on Nov. 15. Cascade School of Performing Arts presents Disney's Frozen Jr. on Nov. 19 and 20, and an Arts Academy Recital is listed for Nov. 21. Check the Center's calendar for those performance times.
The gallery exhibit Four Eights – An Artist Challenge is up through Dec. 14, so you can catch it on the Art Walk night. The week after the parade, the Center lists Crafting with the Classics: Little Women on Tuesday, Dec. 8, at 7 p.m.
The white church, redesigned for rain
Jessica and David Balfour own the historic white church in Old Town, formerly St. Francis, and they have proposed turning it into the Little John's food cart pod. They submitted a complete land-use package to the City of Sherwood on Sept. 1 and expect a four- to six-month review, according to the Sherwood Sun. Counting from Sept. 1, that window runs from about January to March 2027. The project still needs a conditional use permit and other land-use approvals, and the City Council also has to approve the plans.
The design brief is what fits this season. Portland-based Scott Edwards Architecture kept the church building and added a new exterior structure with extra seating so people can gather year-round. Balfour described the request to the Sun:
"We asked them to maintain the vision of the church while adding an exterior building that could support a lot of patrons during the cold and rainy months Oregon has, and I think they delivered wonderfully."
She added that the team sized the outdoor structure after looking at what other pods offer, and that "there will always be a table for someone." This December, the white church will still be a church building on the parade route. If the city approves the plans, it would add covered, year-round seating to Old Town.
Out on Pacific Highway
The highway side of town has added some practical options for the holidays. Ham Ji Bak, a family-run Korean restaurant, opened in June at 21035 S.W. Pacific Highway. It's open Monday through Saturday 11 a.m. to 9 p.m. and Sunday noon to 9 p.m., according to the Sherwood Sun. On July 13, the Sherwood Liquor Store moved next door within Sherwood Plaza. It went from 1,900 to 4,700 square feet and now sells beer and wine, the Sun reported, which makes it a one-stop shop for holiday bottles. And the Chevron car wash at 21090 S.W. Pacific Highway, at Highway 99 and Sherwood Boulevard, has reopened after a renovation. The wash and convenience store are listed as open 24/7, which is handy when wet roads coat the car in December grime.
Holiday closures are posted too. Sherwood Public Library closes Friday, Dec. 25. The drive-up book drop will be locked, but the book drops at the Pine Street entrance stay open.
If you'd like to talk through what Old Town's changes, from the shared room on First Street to the pending plans for the white church, could mean for the blocks around Cannery Square, Josh Halemeier follows these Sherwood projects closely. Schedule a free consultation, and bring your questions.
