The week before Thanksgiving, City crews will start setting Christmas trees into the sidewalk planters along Bay Street. Over the next ten days, sponsors will wire up ornaments and garlands, and the City will plug each finished tree into an extension cord. By December 5 the whole stretch will be lit, closed to cars, and full of people for Holiday on the Bay.
Those sidewalks, planters and traffic lanes are scheduled to be torn out and rebuilt starting early next year. Every holiday event downtown this season happens on the version of Bay Street that the City is about to replace.
Two street names show up on both notices
The City's street-closure notice for Holiday on the Bay lists SR 166/Bay Street from Kitsap Street to Sidney Avenue, plus Frederick Avenue, Robert Geiger Street and Orchard Street. Frederick and Robert Geiger also mark the two ends of the Bay Street reconstruction. In a September 11 message, Mayor Rob Putaansuu laid out the plan:
"Before construction can move forward on both projects, we must first complete the Bay Street reconstruction from Robert Geiger Street to Frederick Avenue."
That comes from the mayor's message on the City of Port Orchard site. He wrote that construction is "slated to start early next year." The work raises the street to prevent flooding, rebuilds the traffic lanes to slow speeds, adds room for cyclists, improves the sidewalks, improves stormwater systems, upgrades streetlights, relocates underground utilities, and updates water and sewer systems.
The "both projects" in that quote are the South Kitsap Community Events Center and Orchard Street Plaza. The Events Center is planned for the site of the current Kitsap Bank building and would house a new Kitsap Regional Library Port Orchard branch, plus event and meeting rooms large and small. The mayor described Orchard Street Plaza as space for outdoor events that doesn't use up downtown's "already strained" parking. Together with Bay Street, the three projects add up to nearly $55 million in downtown investment. The Kitsap Public Facilities District has committed more than $22 million of that to the Events Center.
The timeline has already moved once. In March, the City said a $3.5 million federal award, secured through Sen. Maria Cantwell's office, would push bidding from spring to near the end of 2026 so the street work could line up with the Events Center. That would mean a single stretch of construction downtown instead of two. That's why the street work landed after this holiday season instead of in the middle of it.
Trees go up first, starting the week before Thanksgiving
The Bay Street tree contest is run by the Port Orchard Waterfront Alliance with the City, and this year's theme is "Big, Bold & Bright." The trees are the first holiday decorations to go up downtown and the last to come down. Here's the 2026 schedule from the City's contest sheet:
- November 18–20: City crews set trees into the sidewalk planters along Bay Street.
- Sunday, November 22, through December 1: Sponsors decorate their trees.
- November 23, 25, 27, 30 and December 2: The City expects to hook trees up to power on these days, so trees light up over about a week and a half, not all on one night.
- After December 1: Independent judges score the trees in four categories: Best Traditional, Best Whimsical, Most Beautiful and Overall Best in Show. Ribbons go on the winning trees.
- December 1–26: People's Choice voting at the Port Orchard Market, one vote per person.
- After January 2, and no later than January 7: Sponsors remove their decorations. The City removes the trees and recycles them.
That puts the best evening walk for seeing every tree lit between December 2 and the night of December 5. People's Choice voting stays open past Christmas, so you have plenty of time to vote over the holidays.
November 28, shop by shop
Small Business Saturday is the first big event of the season. The alliance's 2026 page sets it for Saturday, November 28, with a 9:30 a.m. kickoff at the Port Orchard Marketplace, 715 Bay Street. Speakers at the kickoff will talk about shopping local, and Port Orchard Rotary is funding $10 Bay Street Bucks that work like cash at participating businesses. The alliance's event page says the first 100 people get Bay Street Bucks in one spot and the first 50 in another, so plan to be there at 9:30 if you want them.
Here's the day's schedule as posted:
| Where | When | What |
|---|---|---|
| Gig's Emporium | 7–11 a.m. | Stuff-the-bag event; pre-registration required |
| Port Orchard Marketplace | 9:30 a.m. | Kickoff and Bay Street Bucks |
| Port Orchard Library | 10 a.m.–4 p.m. | Friends of the Library book sale |
| Gathered | 11 a.m.–2 p.m. | Santa photos |
| Port Orchard Marketplace | All day | Letter writing, live music, hot cider, Caffe Cocina samples |
| Mercantile in Josephine's | All day | Snowflake making |
| The Brand | All day | Gift wrapping, hot chocolate, vendor market |
| Brick Ally | All day | Letters to Santa |
| The Candy Shoppe | All day | Meet the Grinch |
The Marketplace at 715 Bay Street works as home base for the day. Besides hosting the kickoff, it's where Rustica Grille opened on March 11, 2026, serving breakfast, lunch and dinner. The News Tribune reported that the restaurant would be open daily from 6 a.m. to 10 p.m. and that it took over the space left by The Dock Bar & Eatery, which closed August 31, 2024. This is Rustica's first holiday season downtown, so you can get breakfast before the 9:30 kickoff and come back for dinner after the shops close at 6 without moving your car.
December 5, with the street closed from 2 p.m.
Holiday on the Bay is the biggest event of the season. According to the City's notice, setup and road closures start at 2 p.m. on Saturday, December 5. The event is open to the public from 3 to 7 p.m., and roads should reopen by 8 p.m. The event area covers the Port of Bremerton parking lot, the Water Street boat launch, the Kitsap Bank drive-thru next to Orchard Avenue, and Bay Street itself. The alliance's own calendar lists 3 to 8 p.m. The City's notice is the one that sets the closure, so plan around 3 to 7.
As of late October, the alliance's events page lists the date with "More Info Soon." That page is the place to check for the tree-lighting time, Santa's schedule and the vendor list once they're posted. The alliance also has an older Holiday on the Bay page, but it's a 2024 recap and doesn't reflect this year's program.
The Kitsap Bank drive-thru on that site list matters for the long term. The Kitsap Bank building is where the Events Center is planned to go. This December, the event area includes the corner where the new building and its library branch are expected to stand.
Getting downtown on the two big Saturdays
Parking. The lot at 620 Bay Street, which the City leases from Heritage Bank next to City Hall, is permit-only on weekdays from 6 a.m. to 6 p.m. It's open to the public on evenings and weekends, which covers both November 28 and December 5.
The foot ferry. As of late October, Kitsap Transit's foot ferry page shows all Annapolis sailings canceled until further notice because of mechanical problems. The Port Orchard–Bremerton route is running extra weekday sailings on a temporary schedule that started October 23, and it has no backup vessel until further notice. If you're crossing from Bremerton for either event, check the Port Orchard holiday schedule and the live rider alerts the day you go, since service is changing week to week right now.
The farmers market. The outdoor Saturday market at 933 Bay Street ends its 2026 season on October 31, so it will be closed for both holiday Saturdays. Through the holidays, the indoor Marketplace at 715 Bay Street is the downtown market stop, and it's where People's Choice tree voting happens.
What 2027 has on paper so far
Some pieces are on the record. The mayor's September message puts the start of Bay Street construction in early 2027 and says it has to finish before the Events Center and Orchard Street Plaza can be built. An April 22, 2026 City addendum for the Events Center fundraising campaign also expects construction to begin in 2027. Orchard Street Plaza, once built, is meant to give outdoor events a home that doesn't take over downtown parking.
Other details haven't been published yet. Neither the mayor's message nor the alliance's events page gives a construction length, the order in which blocks will be closed, or a 2027 date or location for Holiday on the Bay, the tree contest or Small Business Saturday. The City's news page and the alliance's calendar are the places to watch for those announcements.
What's settled for 2026 is the schedule above: trees in the planters November 18 through 20, Bay Street Bucks at 9:30 a.m. on November 28, and the street closed to cars from 2 p.m. on December 5.
Our office is just up the road, and we'll be on Bay Street for the tree lighting like everyone else. If you'd like to talk through what the reconstruction means for a home or rental near downtown, or how the work might affect your property, call or stop by Christopher Threet and Greater Peninsula Properties. We're keeping an eye on the City's construction announcements as they come out.
