In March, the Sherwood Sun reported on a new strategic plan for Old Town with a plain finding at its center. The district is busiest in the middle of the day, and the City wants more going on in the mornings and evenings. On Saturday, December 5, that wider day happens for one Saturday. The parade starts at 4:00 p.m. and the tree lighting at Cannery Square Park follows at about 5:00. Around that hour, Old Town has things to do from late morning until well after dark.
The festival hour is short. The day around it is long, and that's where the best part of the Saturday is.
How the Saturday lays out
This is the schedule for December 5, 2026, based on what each organizer has posted.
| Time | What | Where | Cost |
|---|---|---|---|
| 10:00 a.m. | The Hungry Hero Dessert Co. opens | 22567 SW Washington St | Pay as you go |
| 11:00 a.m. to 1:00 p.m. | Pop-Up Maker Space, Sherwood Public Library | Library program | Library event |
| 12:00 p.m. | Heritage Holiday Market and Open House opens | Mosaic Arts Loft, 16017 SW First St | Shopping |
| 3:00 p.m. | 503 Uncorked opens | 22578 SW Washington St | Pay as you go |
| 4:00 p.m. | Holiday parade steps off | Near 12th St and Sherwood Blvd | Free to watch |
| About 5:00 to 5:15 p.m. | Tree Lighting Ceremony | Cannery Square Park, 22622 SW Pine St | Free |
| 7:00 p.m. | The Hungry Hero Dessert Co. closes | Washington St | |
| 10:00 p.m. | 503 Uncorked closes | Washington St |
The festival begins at 4:00 p.m., and its signature moment, the tree lighting, arrives roughly an hour later. The rest of the table runs about twelve hours, from a 10:00 a.m. dessert counter to a 10:00 p.m. wine bar.
Late morning: the library and a market on First Street
The Sherwood Public Library has a Pop-Up Maker Space on the City's calendar from 11:00 a.m. to 1:00 p.m. that Saturday. For families planning to stay into the evening, a hands-on program before lunch spreads the day out so the festival isn't the only thing on the list.
At noon, Mosaic Arts Loft opens its 2026 Heritage Holiday Market and Open House at 16017 SW First Street. The loft describes local artists selling original artwork, prints, handcrafted tree ornaments, holiday cards and home décor. The featured market artist, Ann Brucker, makes paintings and ceramics, from oversized originals for over a mantel to handcrafted mugs and engobe-glazed vases. The vases are paired with dried floral arrangements by Richelle Carkin of Grace and Glory Floral Design.
The market listing also has some practical advice: arrive early, because close-in parking is first come, first served. That matters more on December 5 than on a typical Saturday, because a parade crowd will be heading into the same few blocks by mid-afternoon. A midday arrival gets you the market without the crowds and puts you within walking distance of everything else on the schedule.
Four o'clock: the parade comes down Sherwood Blvd
The Sherwood Robin Hood Festival Association runs the Holiday Festival. The parade starts at 4:00 p.m. near 12th Street and Sherwood Blvd and ends at Cannery Square Park in Old Town. Along the way you'll see the Sherwood High School Marching Band, the Maid Marian Court, festive floats and family-friendly entries, with Santa Claus at the end.
Because the parade ends at Cannery Square, you have two options for where to watch:
- Along the route. You'll see the band and floats up close as they pass, then follow the crowd to the square.
- At or near Cannery Square. You'll catch the end of the parade and already be in place for the tree lighting.
The association invites any family-friendly group to join the parade. Its parade application page lists the entry fee as a suggested donation, not a requirement. Businesses, scout troops and neighborhood groups that want to march should contact the association directly about this year's holiday entries.
The City posts street restrictions on its road and lane closure notifications page. Check it the week of the festival before you drive into Old Town.
About five o'clock: what's free at Cannery Square
The Tree Lighting Ceremony follows the parade, usually around 5:00 to 5:15 p.m. Choirs from several local schools perform, Santa stops by, and the Junior and Senior Maid Marian Court leads a sing-along.
Here's what's free around the square, according to the festival page:
- Santa Tent. Kids can meet Santa and his elves. Free Santa surprise bags are handed out while supplies last, thanks to donations from local businesses.
- Food. Free hot dogs and cookies, with help from the Boy Scouts.
- Warm drinks. Complimentary hot chocolate and coffee, also while supplies last.
- The association's booth. You can buy Festival shirts and learn about the all-volunteer nonprofit that runs both the summer Robin Hood Festival and this December event.
"While supplies last" appears more than once on that list, which is another reason to arrive at the square early. The festival page also links to a volunteer sign-up for anyone who would rather help hand out the cocoa than wait in line for it.
After the lights: Washington Street stays open
Two businesses on SW Washington Street, a short walk from Cannery Square, stay open after the tree lighting.
503 Uncorked at 22578 SW Washington St. is a wine bar with craft cocktails, curated food and live music. Its posted Friday and Saturday hours are 3:00 to 10:00 p.m. That leaves a full evening after the tree lighting for anyone who wants to stay out.
The Hungry Hero Dessert Co. at 22567 SW Washington St. is open 10:00 a.m. to 7:00 p.m. on Saturdays. Families coming from the Santa Tent have nearly two hours after the lighting to stop in for dessert before it closes.
The same Sherwood Sun report names other Old Town businesses as current anchors at different times of day. Symposium Coffee and Sesame Donuts serve the morning crowd, and Cooper Mountain Ale Works serves lunch and dinner. Check their hours for the day before you plan a stop.
Why this Saturday matches the City's plan
The Sherwood Sun piece explains why a festival day like this lines up with where the City wants Old Town to go. Rutledge, speaking for the City, described the district's current rhythm and the gap the plan is meant to fill:
"The planners talk about extending the hours that Old Town is alive and vibrant. Right now, we're really heavy in that midday sector, so we need to expand on the morning and the evening, and typically that's going to be food."
According to the Sun, the City is targeting food, drink and especially wine businesses, as Sherwood builds its identity as a gateway to the surrounding Willamette Valley wineries. Council-approved incentives and clearer permitting guidance are also under consideration to help new tenants move in. The plan also explores curbless street design so that event layouts like tents and booths sit on a flat surface when roads close for festivals.
On December 5, Old Town doesn't need any of those changes to stay busy into the evening. The library program fills the late morning, the First Street market covers the early afternoon, the parade and tree lighting take the late afternoon, and Washington Street keeps going until 10:00 p.m. A good way to spend the day is to park once before noon, walk between all of it, and head home after the wine bar closes.
If the holiday walk through Old Town has you thinking about what your own Sherwood home is worth this season, The Lankheet Group can put together a free home valuation, so you'll have a clear number before the new year.
