Who decorates the Christmas trees along Bay Street? The city's share is small. Public Works sets the trees into the sidewalk planters and runs the extension cords. Everything after that, from the ornaments and garland to the lights and the wire that keeps it all on in a December wind, comes from someone who paid $55 to adopt a planter and then spent a weekend decorating it.
Most of Port Orchard's downtown holiday season works this way. The trees, the Bay Street Bucks on Small Business Saturday, and Holiday on the Bay itself are each funded or staffed by a particular local group, and each one runs on a deadline. Once you know who is behind each piece, you also know when it happens.
The market's last Saturday comes first
Saturday, Oct. 31, is Closing Day & Trick or Treat at the Port Orchard Farmers Market, open 9 a.m. to 2 p.m. on the waterfront at 933 Bay St. That ends a Saturday season that began April 4. The market's 2026 schedule doesn't list a winter or holiday market after it. The midweek market that West Sound Magazine covered when it launched this summer at South Kitsap Helpline, 4215 SE Mile Hill Drive, already finished its run on Sept. 30.
After Oct. 31 the waterfront has no regular weekly anchor, and a set of one-off dates takes over:
| Date | What happens | Where | Who runs it |
|---|---|---|---|
| Sat., Oct. 31 | Farmers Market Closing Day & Trick or Treat | 933 Bay St. | Port Orchard Farmers Market |
| Nov. 18–20 | Trees placed in sidewalk planters | Bay Street | City of Port Orchard |
| Sun., Nov. 22 to Tues., Dec. 1 | Sponsors decorate their trees | Bay Street | Tree sponsors |
| Sat., Nov. 28 | Small Business Saturday, 9:30 a.m. kickoff | Port Orchard Marketplace, 715 Bay St. | Port Orchard Bay Street Association |
| Sat., Dec. 5, morning | Santa Sleighs 5K and Kids Reindeer Run | McCormick Woods Golf Course | South Kitsap Rotary |
| Sat., Dec. 5, afternoon | Holiday on the Bay | Downtown waterfront | Bay Street Association with community partners |
| Dec. 1–26 | People's Choice voting on the trees | Port Orchard Market | Port Orchard Waterfront Alliance |
Every lit tree on Bay Street has a sponsor
The 2026 Bay Street Tree Decoration Contest rules, issued jointly by the Port Orchard Waterfront Alliance and the City of Port Orchard, lay out each step. Reservations opened Sept. 1. A sponsor pays $55 to the city, plus a 3% fee for paying by card, and lists a first, second, and third choice of planter number from a map. Having sponsored a planter before doesn't hold it for you this year. The rules also say "there is always a waiting list."
The $55 covers only the planter. The form tells sponsors to plan on spending at least another $60 on lights, ornaments, and decorations, and it calls the whole thing "a donation to the holiday atmosphere of your community." Here is the schedule a sponsor works to this year:
- Nov. 18–20: City crews set the trees in the planters and attach a tag with each sponsor's name and number.
- Nov. 22 through Dec. 1: Sponsors decorate. Every tree must be fully decorated by Dec. 1. Sponsors who can't finish are asked to say so early so the spot can go to someone on the wait list.
- Power hookup: Sponsors email the city when their tree is finished, and the city connects the lights on Mondays, Wednesdays, and Fridays: Nov. 23, 25, 27, and 30, and Dec. 2.
- After Dec. 1: Independent judges award Best Traditional, Best Whimsical, Most Beautiful, and Overall Best in Show. Winners are announced on social media and get ribbons on their trees.
- Dec. 1–26: People's Choice voting takes place at the Port Orchard Market, one vote per person.
- Jan. 2–7: Sponsors take their decorations down. The city removes the trees and recycles them, and anything left on a tree after Jan. 7 gets thrown out.
The rules explain why the trees look the way they do. LED lights are required, and every tree has to be lit. Commercial and advertising trees aren't allowed, and neither are giving or charity trees. A business can work a nod to itself into the theme, but the rules say the focus has to be "a fully decorated Christmas tree." This year's form adds something new. The city asks sponsors to water the soil around the trunk after decorating and again through December if they can, and it says Public Works is working on holding the trees more securely in the planters. Sponsors are also told to wire decorations to the branches so they stay put in wind.
For a sense of scale, Kitsap Daily News reported 54 community-decorated trees lining the sidewalks for the 2024 event.
Why the festival became a coalition
The trees show how the bigger event is organized, and that setup is fairly new. For 25 years, downtown's December celebration was the Festival of Chimes & Lights. In 2024 it was reworked and renamed Holiday on the Bay. Kitsap Daily News reported that the previous year's festival ran into trouble when ongoing construction affected decorations and tree placement. For 2024, the Port Orchard Bay Street Association and the city formed a Christmas Coalition, with help from the South Kitsap chamber, Port Orchard marina, Fathoms O' Fun, New Life Church, and Port Orchard Ford.
In that same Kitsap Daily News story, Samantha Rolstad, owner of Josephine's Mercantile and Revival and the event's primary coordinator, described the arrangement this way: "It's like baking a big pie, with each partner taking a slice." The same article quoted Shane Wood of Port Orchard Ford, who said the event had "some funding from the city" and was otherwise built on community support.
The idea of each group taking a slice carries through the whole season. Last December, Western Washington Center for the Arts performed on the Holiday on the Bay main stage and led community caroling at the end of the night, according to a Port Orchard Independent report carried by Kitsap Daily News.
Small Business Saturday is funded the same way
The Saturday after Thanksgiving, Nov. 28, follows the same pattern on a smaller scale. The Bay Street Association's Small Business Saturday page sets the kickoff for 9:30 a.m. at the Port Orchard Marketplace, 715 Bay St. Early arrivals get $10 in Bay Street Bucks, which work like cash at participating downtown businesses that day. The Bucks are paid for by a donation from the Port Orchard Rotary, and only a limited number are handed out, so it pays to be there at the start.
The rest of the day's listed schedule is also run by individual groups and businesses:
- Gig's Emporium: a Stuff the Bag event from 7 to 11 a.m., with pre-registration required.
- Port Orchard Library: a Friends of the Library book sale from 10 a.m. to 4 p.m.
- Gathered: Santa photos from 11 a.m. to 2 p.m.
By Nov. 28, the trees along Bay Street are in their decorating window, so some may be fully decorated and others still bare.
December 5 is a two-event Saturday
The busiest day of the season is the first Saturday in December, and it begins away from the water. The South Kitsap Rotary's Santa Sleighs 5K is on Dec. 5 at McCormick Woods Golf Course, 5155 McCormick Woods Drive SW. The free Kids Reindeer Run starts at 9:30 a.m. and the 5K at 10 a.m. Kitsap Daily News reported that the race took the place of the old Jingle Bell Run when the downtown festival was reworked in 2024.
Holiday on the Bay starts downtown that afternoon. The City of Port Orchard's street-closure notice, posted Sept. 24, gives the timing and footprint:
- 2 p.m.: Setup begins and roads close.
- 3 to 7 p.m.: The event is open to the public.
- By 8 p.m.: Cleanup is finished and roads reopen.
- Event area: The Port of Bremerton parking lot, the Water Street Boat Launch, and the Kitsap Bank drive-thru next to Orchard Avenue.
- Closed streets: SR 166/Bay Street from Kitsap Street to Sidney Avenue, along with Frederick Avenue, Robert Geiger, and Orchard Street.
The Bay Street Association's event calendar lists the event as 3 to 8 p.m. Either way, Bay Street through downtown will be closed from mid-afternoon into the evening, and the city notice warns of heavy congestion and suggests taking other routes. If you live up the hill and usually drive down Bay Street, it's easier to walk down or plan your errands around those hours.
The same afternoon, a Casa Collective Holiday Market is listed for 2 to 8 p.m. at Gathered by Jo's, 702 Bay St.
What's still to be posted
A few parts of the season haven't been announced yet. The Bay Street Association lists Holiday on the Bay for Dec. 5 with "More Info Soon," and the 2026 stage lineup, tree-lighting time, and Santa details haven't been posted. Its Holiday on the Bay page still shows material from earlier years, so last year's times may not apply this year.
The Port Orchard Yacht Club's Lighted Boat Parade page still shows its 69th annual parade on Saturday, Dec. 13, 2025, which started near Southworth just after dusk and was estimated to reach downtown Port Orchard around 7:35 p.m. When the club posts its 2026 date, it will show up on that page.
The Port Orchard Public Market at 715 Bay St. is an indoor space shared by several independent businesses, as the Kitsap Sun has described it, so holiday hours vary by tenant. If you plan to vote for your favorite tree there, check the hours of the shop you'll be visiting first.
If you sponsor a tree this year, run on Dec. 5, or have a favorite stop along Bay Street in December, I'd love to hear about it. And if you ever have questions about life or real estate in Port Orchard, Wendy Crenshaw is a local who's always happy to talk. Let's Connect.
