Downtown Port Orchard's Halloween takes up all three days of the weekend before Halloween, Friday, Oct. 23 through Sunday, Oct. 25, 2026. It happens in small pieces: a library storytime, a teen dance, a trivia night, a parking-lot trunk or treat and a bingo card that sends families from shop to shop. The schedule makes the most sense once you see how few buildings it relies on, and why the city wants to change that.
What Changed From Boo Bash
For years the Port Orchard Bay Street Association ran a downtown trick-or-treat called Boo Bash. The association's events page explains the replacement plainly:
"Port Orchard's Annual Downtown Trick or Treat event, Boo Bash, has been reimagined and redesigned to be safer, sustainable and more merchant friendly."
The new event, Halloweekend, runs the whole weekend before Halloween, and the association asks people to wear costumes downtown and join in. The organizer lists the home base as the downtown waterfront along Sidney Parkway, at the cross streets of Sidney Avenue and Bay Street. One small catch: the location block on that page still reads "October 23-25, 2025," but the association's events page and the day labels in the schedule match the 2026 calendar, with Friday falling on 10/23. One sentence on the events page gives the start as Friday, Oct. 22, but Oct. 22 falls on a Thursday this year, and the heading on that same page reads October 23-25, 2026.
"Merchant friendly" shows up in the schedule. Most events are hosted by a specific business or institution, run on its own hours, and are spread out so that no single block has to take everyone at once.
Friday Splits Up by Age, on Both Sides of the Street
Friday, Oct. 23 starts with the youngest group. The Port Orchard Library holds a Halloween Storytime & Costume Parade at 11 a.m. for ages 2 to 6 and their caregivers, and the parade trick-or-treats through the library.
That evening, two events run at the same time, 6 to 8 p.m., on facing sides of Bay Street. Monster Mash at Gathered is for ages 13 to 18, with a DJ, face paint, spooky crafts and games with prizes. Haunted Trivia Night is at The Merc inside Josephine's, and the organizer's own description pitches it as a place for parents to go once they've dropped teens off: "Drop your teens off at the Monster Mash and cross the street to the Merc for some spooky trivia and delicious hot drinks."
Those two spaces are one business. Gathered by Josephine's is the shop's second location, selling vintage, found and curated goods and doubling as a community gathering and event space at 702 Bay St. The Merc is Josephine's in-store coffeehouse, and the downtown association lists Josephine's at 701 Bay St. So Friday night amounts to one family of shops hosting two age groups across a single crosswalk.
Saturday, Door by Door
Saturday, Oct. 24 is the full day. Sorting it by address shows how little ground it covers.
| Time | Event | Where |
|---|---|---|
| 9 a.m.–2 p.m. | POP Kids Club Halloween & Harvest Crafting, ages 3–12 | Port Orchard Farmers Market, 933 Bay St. |
| 10 a.m.–4:30 p.m. | Haunted Escape Room, registration required | Port Orchard Library |
| 11 a.m.–4 p.m. | Pictures with a Witch | Sidney Art Gallery & Museum, 202 Sidney Ave. |
| 11 a.m.–5 p.m. | Ghostly Goose Chase | Participating merchants |
| Noon–5 p.m. | SKFR Haunted Ambulance & PO Police Touch-a-Truck | Lot next to Dude's Donuts, 632 Bay St. |
| 2–4 p.m. | Costume Contest | Gathered, 702 Bay St. |
| 4–6 p.m. | Fathoms O' Fun Trunk or Treat | Parking lot by the Gazebo and Marina Park |
| Time TBD | Haunted Backstage Alley | Polaris Theatre, 822 Bay St. |
One schedule conflict to know about. The Halloweekend page puts Pictures with a Witch and the Costume Contest on Saturday, but the association's Ghostly Goose Chase flyer lists both under Sunday, Oct. 25. The costume contest flyer gives the 2–4 p.m. time and an October date but doesn't say which day. Check with the Port Orchard Bay Street Association or Gathered before you plan around either event.
A few of these deserve more detail. At the farmers market crafting session, kids paint pumpkins, do a market scavenger hunt and play games, and each participant gets a $4 token to spend on produce from the market's farm vendors. The market is in its 48th season and runs Saturdays from 9 a.m. to 2 p.m. through Oct. 31, so Halloweekend Saturday is the second-to-last market of 2026.
The costume contest at Gathered has categories for both kids and adults. Kids compete for most creative, best DIY or homemade, and cutest. Adults compete for best group, scariest and funniest. The library's escape room requires registration through Kitsap Regional Library at krl.org.
Polaris Theatre's alley is the one listing without a time. The historic theatre at 822 Bay St. is still under renovation, with construction and fundraising ongoing, and its backstage alley has hosted community events since 2024. The theatre hasn't yet posted the format or hours for this year's haunted alley, so check closer to the date.
Saturday's two biggest crowd events, Touch-a-Truck and Trunk or Treat, are both in parking lots. Halloweekend uses whatever open pavement downtown has, and that gap is what the city's plans are meant to fill.
The Goose Chase Finishes at the Library
The Ghostly Goose Chase runs all three days: 11 a.m. to 5 p.m. on Friday and Saturday, and 1 to 5 p.m. on Sunday. It's a bingo hunt. Geese are hidden at participating merchants, and each one you find earns a small treat. Turn in a full bingo card at the library during open hours for a larger treat and a chance at a prize basket. The organizer's instructions don't say where to pick up a card or whether it costs anything, so ask at the first shop you visit.
On the Halloweekend page, Sunday, Oct. 25 is the lightest day. Besides the Goose Chase, the Port Orchard Library hosts Hushed Halloweekend from 1 to 4 p.m., a sensory-friendly family program open to all ages. That makes the library the most-used venue of the weekend. It hosts Friday's storytime, Saturday's escape room and Sunday's sensory program, and it's where every Goose Chase card gets turned in.
The library also features in the city's downtown plans. The planned South Kitsap Community Events Center, on the site where the Kitsap Bank building now stands, would include a new Kitsap Regional Library Port Orchard branch along with large and small public event and meeting spaces.
Getting Downtown This Year
The waterfront looks a little different than it did last October. A few things to check before you go:
- The boardwalk. The Port of Bremerton closed the 436-foot wooden waterfront boardwalk on Thursday, June 4 after inspectors found structural concerns. At the time, the Port gave no estimate for reopening. An engineering report on the Port Orchard Marina boardwalk was on the Port Commission's Sept. 22 agenda, but we couldn't find a published decision on reopening. Check with the Port before planning a walk along it.
- The foot ferry. Kitsap Transit's foot ferry leaves Bremerton every 30 minutes for downtown Port Orchard. It costs $2 per ride, paid in cash or with an ORCA card, and no advance ticket is needed. Kitsap Transit's current Port Orchard/Bremerton schedule took effect Sept. 28, 2026, and the agency says the route is without a backup vessel "until further notice." Check service alerts the morning you ride.
- Parking. The organizer says street parking is free and available all evening. Its driving directions point you to Frederick, Sidney or Harrison avenues to reach the main lots on the water side of Bay Street. Keep in mind that one of those lots by the Gazebo and Marina Park becomes the Trunk or Treat from 4 to 6 p.m. on Saturday.
The Street Under Halloweekend
All of this happens on a Bay Street that is scheduled for reconstruction. In a mayor's message posted Sept. 11 and updated Oct. 2, 2026, the city says construction on the SR 166 Bay Street Reconstruction is "slated to start early next year." That timeline has already moved once. A January report described spring 2026 construction with completion by December 2026.
The project covers Bay Street from Robert Geiger Street to Frederick Avenue. Plans include raising the street to prevent flooding, rebuilding traffic lanes to slow speeds, adding room for cyclists, improving sidewalks, and upgrading stormwater, streetlights, utilities, water and sewer. According to the city, Bay Street has to be finished first. Only then can construction move forward on the Community Events Center and the Orchard Street Plaza, which together with the street work add up to nearly $55 million in downtown investment. The Kitsap Public Facilities District has committed more than $22 million to the events center.
The mayor's message describes the plaza in terms that match this month's schedule. It would provide "space for our outdoor events that doesn't utilize our already strained downtown parking." This year, the biggest outdoor events of Halloweekend still take place in a parking lot by the Gazebo and in the lot next to Dude's Donuts, while a set of shops, a gallery, a theatre alley and the library host everything else. That arrangement is what the downtown association built when it replaced Boo Bash. The city's plans would eventually give events like this a plaza and an events center to work with, after Bay Street is rebuilt.
After Halloween, the downtown calendar's next big date is Small Business Saturday on Nov. 28, 2026, from 9:30 a.m. to 6 p.m. It kicks off at the Port Orchard Marketplace, 715 Bay St., with downtown shopping and Bay Street Bucks.
If you're wondering how changes on Bay Street could affect daily life or a future move in South Kitsap, the Scott Ahern team is happy to talk it through with you, no pressure. Book an Appointment and bring your questions.
