Mosquito Fleet Fest - Celebrate Port Orchard’s Maritime Culture & History on the Waterfront
The 3rd annual Mosquito Fleet Fest on the Port Orchard waterfront is May 23+24th, 2026!
The Mosquito Fleet was the name of a vast array of steamships that ferried people and goods around the Kitsap Peninsula before the advent of automobiles in the late 1800’s to the 1920’s. At this time, maritime vessels, like steamers, tall ships, and canoes, were the only reliable way to stay connected with other communities and the outside world. To celebrate this unique heritage, the Port Orchard Waterfront Association of merchants is hosting the 2nd Annual Mosquito Fleet Fest! Here’s what to expect and how to get the most out of the weekend event!
Step aboard one of the last surviving mosquito fleet-era boats!
The CARLISLE II is one of the LAST surviving and operating ships from the era of the Mosquito Fleet. With opportunities to step aboard this ‘floating museum’ and even experience a sailing…this is a fascinating way to get hands on with Kitsap’s maritime past.
Virginia V Sailings
The Virginia V is back this year! A gorgeous Mosquito Fleet steamer, designated a historic landmark, was preserved to promote maritime history and ensure her continued seafaring.
Sailing is expected to be available for purchase soon. Additional details will be posted here once they are officially announced.
story sails with josh farley
The CARLISLE II Story Sail is a 90-minute sail departing and returning to Port Orchard Foot Ferry Terminal at the Port Orchard Marina. The guided tour experience will give you lots of time to enjoy the shoreline and scenery as you learn about Kitsap’s Mosquito Fleet history with guest narrator and local historian Josh Farley.
This year, there will be three sailings to choose from on Saturday only. Additional details will be posted here once they’re officially announced.
maritime market
9AM-5PM - you’re invited to shop at the Mosquito Fleet Fest Maritime Market - a collection of local artisans and vendors at the Port Orchard Marina.
Historic Storywalk
A guided tour through downtown Port Orchard, learning about historic buildings, landmarks, and their purpose during the Mosquito Fleet era.
experience the port orchard farmers market
From 9AM-2PM (Saturday Only), the longest-running Farmers Market in Kitsap attracts vendors and visitors from around the region. Shop for locally produced plants, veggies and greens, meats, florals, art, food, crafts, wine, coffee, and so much more at the Port Orchard Marina parking lot.
artisan alley
9AM-5PM - Local artists will be gathering in the outdoor space against the giant underwater mural adjacent to the Port Orchard Public Market.
scavenger hunt
The Kitsap Regional Library is supplying materials for a fun and interactive waterfront scavenger hunt!
Family Fun Zone
12PM-4PM - Stop by Polaris Theater for knot tying, music, nautical art, bubble machine parties & more!
Kitsap Ferries Panel
Panel presentation on the history & future of ferries in the Puget Sound with local community leaders like Commissioner Katie Walters, John Clauson, Steve Sego, Carla Sawyer, Ed Brown, and moderated by Josh Farley. Saturday only at 4pm.
Visit Port Orchard and stay awhile
Great places to eat & drink in Downtown
There are too many amazing places to eat in and near downtown Port Orchard to list, but here are a few favorites we’re sure you’ll love!
Mercantile Coffee Co.
This beloved cafe inside Josephine’s Mercantile serves up great coffee, yummy pastries, and snacks.
The Brickhouse
This Bay Street family-friendly restaurant has an amazing outdoor patio area with murals of the old Mosquito Fleet.
Carter and co Chocolates
Treats, ice cream, pastries, sandwiches, in-house chocolates, and a full-service cafe make Carters a Bay Street fave!
Khao soi
This new Thai food space on Bay Street has quickly become known as one of the very best on the Kitsap Peninsula.
Thai charlies
This cozy Thai joint is great for dine-in or take-out to make a picnic on the waterfront.
la palapa mexican grill
Tasty Mexican classics on the Port Orchard Waterfront make La Palapa a winner in our book!
The Coffee Oasis
An excellent coffee shop with a small wrap, breakfast, and sandwich menu - all proceeds go to helping teens facing homelessness.
Peninsula bevco
A VAST tap list with an adjacent bottle shop that stocks a ton of boozy beverages. Bevco also has a menu full of yummy appetizers and entrees.
damn fine pizza
This big pizzeria with waterfront views slings awesome pizza, salads, appetizers, and more, sporting a full bar and a popular pinball room.
additional kitsap articles & guides below
Stunning beachfront on the shores of Port Orchard with unobstructed, waterfront vistas from inside the window-lined living area and furnished deck beneath by a canopy of trees.