"The nice thing is when we're here, they're usually not, and when they have their classes in session, we're not," Olea Vineyards co-owner Tom Melillo told the Sherwood Sun last summer. He was describing how his family's new tasting room shares 16017 SW First St. with Mosaic Arts Loft.
Most weeks, the arrangement works because the two businesses use the room at different times. In the first week of December, Mosaic's holiday market is scheduled for exactly the hours Olea listed for its tasting room when it opened. That Saturday afternoon, the market also overlaps with the parade, the tree lighting and the Santa tent a few blocks away. From the Tuesday Art Walk to the Saturday parade, the week runs through that one storefront and the streets around it.
A Storefront Built on Two Schedules
Olea Vineyards is family owned by Tom and Melinda Melillo. They held a ribbon-cutting for the Old Town location on July 8. The original tasting room on Parrett Mountain is becoming a members-only lounge and event space, so First Street is now the walk-in option. No reservation is needed.
When it opened, the Sherwood Sun reported these hours:
- Fridays, 3 to 7 p.m.
- Saturdays, noon to 6 p.m.
- Sundays, noon to 5 p.m.
Melillo told the paper the most popular bottles are the sparkling rosé, the big reds and the estate pinot.
The rest of the time, the room belongs to Mosaic Arts Loft and its classes. "It's a great common space because we get to see all the artwork that they create," Melillo said in the same Sherwood Sun piece.
The first week of December shows the arrangement in action. It starts on a Tuesday night.
Tuesday, December 1: The Art Walk Starts on Pine Street
The Old Town Sherwood Winter Art Walk runs Tuesday, December 1, 2026, from 5 to 8 p.m. It's free. Sherwood Center for the Arts at 22689 SW Pine St. is the place to start. Route maps are available there, and the walk pairs artists, vendors and musicians with downtown businesses.
From the Center it's a short walk to First Street, where Mosaic Arts Loft has posted its own lineup of professional and teen student artists, billed as a holiday gift collection:
| Artist | What they're bringing |
|---|---|
| Ann Brucker | Vases with dried florals, clay textured ornaments, painting prints |
| Jaelynn Harris | Watercolor landscape cards and mini painted ornaments |
| Christina Coonradt | Pottery for the table |
| Ryland Potruch | Colored pencil birds and Northwest landscape drawings |
| Simon Slick | "Mr Mole" adventure stories in ink |
| Daphne Adams | Mt Hood oil painting puzzles and prints |
| Waylon Zabriskie | Tree watercolor cards and prints |
| Mariia Ukhova | Floral still-life ink drawing prints and cards |
The list also includes framed prints of still-life oil paintings by a high school senior who has taken art lessons at Mosaic since first grade.
Tuesday isn't one of Olea's listed days, so on Art Walk night the room is Mosaic's. That changes three days later.
Friday and Saturday: The Market Lines Up With the Tasting Room
On its Art Walk page, Mosaic lists the Heritage Holiday Market as its next event. Resident artists will host on Friday, December 4, and Saturday, December 5. Compare those hours with the tasting room's listed hours:
| Day | Heritage Holiday Market | Olea tasting room hours, as reported in August |
|---|---|---|
| Friday, Dec. 4 | 3 to 7 p.m. | 3 to 7 p.m. |
| Saturday, Dec. 5 | Noon to 6 p.m. | Noon to 6 p.m. |
| Sunday, Dec. 6 | No market listed | Noon to 5 p.m. |
The hours match to the minute. Olea's winter schedule may differ from what it posted in summer, so check with the winery before planning around a glass. Even so, this is the one weekend on the calendar built around the hours the two businesses share, after months of using the room at different times.
The details of the market reward showing up early. Door prizes go to the first five guests. On Saturday there's an add-on workshop called "Create and Chocolate," a ceramic coaster painting session. Space is limited, and you have to pre-register through Mosaic's events page. The market is pitched at gifts for family, teachers and friends.
The Saturday market hours also leave two hours of overlap with the biggest event of the week.
Saturday, December 5: Old Town at Its Busiest
The Sherwood Robin Hood Festival Association runs the annual Holiday Festival with support from the City of Sherwood, local sponsors and volunteers. It's always on the first Saturday of December, which this year is December 5, from 4 to 6:15 p.m. The association announced the details in the Sherwood Sun.
Here's how Saturday runs in Old Town:
- 11 a.m. to 1 p.m. The City of Sherwood's events calendar lists a Pop-Up Maker Space.
- Noon. The Heritage Holiday Market opens at 16017 SW First St. The first five guests get door prizes.
- 3:15 p.m. Parade entries line up along SW 12th Street next to the Kohl's parking lot. A registration table is set up near one of the SW 12th Street entrances to Kohl's.
- 4 p.m. The parade steps off at SW Sherwood Boulevard and SW 12th Street and winds its way to Cannery Square Park at 22622 SW Pine St.
- After the parade. The Junior and Senior Maid Marian Courts host the festivities at Cannery Square. Local choral groups perform, the tree is lit, and Santa and his helpers hand out bags of goodies to children while they last. Free hot dogs and cookies are also served while supplies last.
- 6 p.m. The holiday market closes on First Street.
- 6:15 p.m. The festival wraps up.
Every season, association volunteers assemble 300 to 400 of them for this one evening. With that many bags and a "while supplies last" promise, families with young kids have a good reason to be at Cannery Square when the parade arrives instead of lingering on First Street.
The parade is open to families and community groups, but it isn't walk-up. All participants must register online at robinhoodfestival.org. The association also takes volunteers for the festival and holds meetings at 7 p.m. on the third Thursday of each month.
The festival's own announcement suggests coming early to shop and eat in Old Town before the parade. The market opens at noon, which leaves time for First Street before the parade steps off at 4 p.m. and heads for Cannery Square.
Around the Week: Library Dates on Each End
The City of Sherwood events calendar also lists a Sound Bath Meditation on Thursday, December 3, from 6 to 7 p.m.
Before any of this, Thanksgiving week changes the library's hours. Sherwood Public Library services end at 5 p.m. on Wednesday, November 25, and the library is closed November 26 and 27. Holds you were planning to pick up that week need to come home by Wednesday afternoon.
At the other end of the month, the library's Noon Year's Eve Party runs Thursday, December 31, from 11 a.m. to noon. There will be juice, cookies, party hats, crafts, games, dancing and a countdown to midday.
Between those two library dates, the busiest five days are December 1 through 5. The Art Walk sets them off on Pine Street, the market runs on First Street for two afternoons, and on Saturday the parade ends at Cannery Square.
If you live close enough to walk to Cannery Square on December 5 and wonder what that location is worth today, Chandler Willcuts can give you a clear read on your Sherwood home before the new year. Get Your Free Home Valuation.
