On Friday morning, the costumes start lining up at the Port Orchard Library. Storytime starts at 11 AM and ends with a costume parade that trick-or-treats through the stacks. The Ghostly Goose Chase opens at the same hour and runs until 5. By evening, teenagers are at a DJ party inside Gathered, and their parents are across the street at The Merc inside Josephine's for haunted trivia and hot drinks.
This is Halloweekend, the Port Orchard Waterfront Association's replacement for its annual downtown trick-or-treat event, Boo Bash. It's also the last fall on Bay Street as it stands now. The City of Port Orchard expects to start rebuilding SR 166/Bay Street early next year. The street from Robert Geiger Street to Frederick Avenue will be raised to keep the water out. The two changes point the same way. Downtown's big gatherings are leaving the curb and moving into storefronts, the library and dedicated public space. The rebuild finishes a shift that this weekend's schedule has already started.
The Halloween Party Already Left the Curb
Boo Bash was the association's annual downtown trick-or-treat event. The Waterfront Association says it has "reimagined and redesigned" the event to be "safer, sustainable and more merchant friendly." It now runs across the whole weekend before Halloween. Home base is the downtown waterfront at Sidney Parkway, near Sidney Avenue and Bay Street. Nearly every listing on the schedule, though, sits inside a business, the library or a parking lot.
Here's the weekend, per the Waterfront Association's Halloweekend schedule. The association's events calendar lists this year's dates as October 23 to 25, 2026, which puts it Friday through Sunday.
Friday, October 23
- Ghostly Goose Chase, 11 AM to 5 PM
- Halloween Storytime & Costume Parade at the Port Orchard Library, 11 AM, for ages 2 to 6 and their caregivers
- Monster Mash at Gathered, 6 to 8 PM, with a DJ, face paint, crafts and games with prizes, for ages 13 to 18
- Haunted Trivia Night at The Merc inside Josephine's, 6 to 8 PM
Saturday, October 24
- POP Kids Club Halloween & Harvest Crafting at the Port Orchard Farmer's Market, 9 AM to 2 PM, with pumpkin painting, a scavenger hunt and games for ages 3 to 12. Each child gets a $4 token to spend with the market's farm vendors.
- Haunted Escape Room at the Port Orchard Library, 10 AM to 4:30 PM. Registration is required through Kitsap Regional Library.
- Ghostly Goose Chase, 11 AM to 5 PM
- Pictures with a Witch at Sidney Art Gallery & Museum, 11 AM to 4 PM
- SKFR Haunted Ambulance & PO Police Touch-a-Truck in the lot next to Dude's Donuts, noon to 5 PM
- Polaris Theatre Haunted Backstage Alley trick-or-treating, 1 to 3 PM
- Costume Contest at Gathered, 2 to 4 PM, for kids and adults
- Fathoms O' Fun Trunk or Treat in the parking lot by the Gazebo and Marina Park, 4 to 6 PM
Sunday, October 25
- Ghostly Goose Chase, 1 to 5 PM
- Hushed Halloweekend at the Port Orchard Library, 1 to 4 PM, a sensory-friendly family program for all ages
On Saturday, the Farmer's Market crafting, the library escape room and the Goose Chase all overlap before noon, so you can pack the morning. The touch-a-truck, the Polaris alley and the Gathered costume contest fill the early afternoon. Trunk or Treat by the Gazebo wraps up the day just as it gets dark.
The organizers' own directions show how tight downtown parking is. Drivers are told to turn toward the water on Frederick Avenue, Sidney Avenue or Harrison Avenue to reach the main lots. Street parking is free. The easier way in is across Sinclair Inlet. Kitsap Transit foot ferries leave Bremerton every 30 minutes and cost $2 a ride, paid in cash or with an ORCA card, with no advance ticket needed. The Bremerton foot ferry dock sits beside the Washington State Ferries terminal.
Thanksgiving Weekend Moves Into the Shops
Small Business Saturday follows the Halloweekend model and spreads even further into the storefronts. The Waterfront Association's event page lists Saturday, November 28, 2026, from 9:30 AM to 6 PM, and says more details are still coming. The schedule so far:
- A 7 to 11 AM "Stuff the bag" event at Gig's Emporium
- A 9:30 AM kickoff at Port Orchard Marketplace, where the first arrivals get $10 in Bay Street Bucks to spend downtown
- A library book sale, 10 AM to 4 PM
- Santa photos at Gathered, 11 AM to 2 PM
- All-day activities at Josephine's Mercantile, Port Orchard Marketplace, The Brand, Brick Ally and The Candy Shoppe
Bay Street Bucks go to whoever reaches the kickoff first. If you want the $10, be at Port Orchard Marketplace by 9:30.
December 5 Is the One Night Bay Street Still Closes for a Crowd
Holiday on the Bay is the season's only event that still needs the street itself. The City of Port Orchard has confirmed it for Saturday, December 5, 2026, open to the public from 3 to 7 PM. Setup and road closures start at 2 PM, and streets reopen by 8 PM. The closures cover SR 166/Bay Street from Kitsap Street to Sidney Avenue, plus Frederick Avenue, Robert Geiger Street and Orchard Street. If you live or park near those blocks, plan your Saturday afternoon errands around the 2 PM closure.
The Waterfront Association hasn't posted a full 2026 lineup yet. Its most recent posted schedule gives a sense of the format. A holiday market filled the Kitsap Bank parking lot, and a Port Orchard Ford shuttle ran from 3 to 8 PM. There were Santa photos, crafts and a pet parade with the library, karaoke at the Polaris Theater, and lighted boats from Port Orchard Marina. A holiday march and the tree lighting came after dark. Check the Holiday on the Bay page closer to the date for this year's schedule.
What Gets Built Under the Next Holiday Season
The Bay Street project was supposed to start sooner. In January, the Port Orchard Independent reported construction beginning in April. In March, the city announced that Sen. Maria Cantwell's office had secured $3.5 million in Congressionally Directed Spending for the project. That moved the bid to late 2026 and construction to 2027. Kitsap Daily News and the Kitsap Sun both reported the award. The delay was on purpose. In the city's announcement, Mayor Rob Putaansuu explained the timing:
"With these new dollars, we can now align the construction of this project with the new South Kitsap Community Event Centre project, ultimately lessening the construction impact timelines for downtown."
According to the city, Bay Street will be raised to prevent flooding and address sea level rise. Traffic lanes will be rebuilt to slow speeds, and the street will get room for bikes and better sidewalks. Underground, crews will rebuild stormwater, water and sewer lines, move overhead utilities below ground, and upgrade the streetlights. The city hasn't published a construction timeline, phasing plan or detour map yet. For now, "early next year" is the most specific start date available.
In his September 11 message, the mayor said Bay Street has to be finished before construction can move ahead on the two projects that follow it. The South Kitsap Community Events Center and the Orchard Street Plaza bring the three-project downtown investment to nearly $55 million. The Kitsap Public Facilities District has committed more than $22 million to the Events Center.
The Places Hosting This Fall Are the Ones That Change Next
The full list of what's planned fills in this fall's schedule. The Events Center will go where the Kitsap Bank Building stands now, and it will house a new Kitsap Regional Library Port Orchard branch along with large and small event and meeting spaces. That's the same library system running the storytime parade, the haunted escape room and Hushed Halloweekend this month. Kitsap Bank's parking lot has hosted the Holiday on the Bay market.
The plaza addresses the same parking problem behind the Halloweekend directions. The mayor's message says the Orchard Street Plaza "will provide space for our outdoor events that doesn't utilize our already strained downtown parking." The Waterfront Association redesigned Halloween around shops and venues, and the city is building a dedicated home for outdoor events. The stretch from October 23 through December 5 is the last stretch of events scheduled on Bay Street before the rebuild.
If you own a home near downtown Port Orchard and want to know how the Bay Street rebuild and the new Events Center could affect its value, Serving The Sound can help. Request a free home valuation, and Anne Watkins will walk you through what's planned for the blocks around you.
