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.
May 22nd, Port Orchard Dryft Concert
An intimate, wooden steamship experience aboard the Virginia V with two of the region's most talented singer/songwriters. You'll join a small crowd of fellow concert-goers on the wood-and-windows encased main deck and settle in for an extraordinary evening.
Escape on the beautiful waters of Sinclair Inlet and unwind with stunning views, easygoing vibes, and a welcoming snack and beverage bar. It’s the perfect outing for families—sit back, enjoy a treat, and soak in the sights of Puget Sound.
When docked, Virginia V will be available for public, dockside tours.
This vessel is not ADA-compliant
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.
DRYFT CONCERTS
Intimate concerts in historic spaces
In Partnership with the Virginia V Foundation as part of the America 250 celebrations, DRYFT Music is producing two intimate concerts in Kitsap, featuring some of the region's most talented singer-songwriters.
Concerts will take place on board the Virginia V steamship, which will remain docked during the concert.
Additional ticket sales will be available at the door if space allows.
Port Orchard Waterfront
Friday, May 22nd
Poulsbo Waterfront
Thursday, May 28th
Historic Storywalk
A guided tour through downtown Port Orchard, learning about historic buildings, landmarks, and their purpose during the Mosquito Fleet era.
Starting Location: Waterfront Park | Sunday, May 24th, 12pm
Lasting approximately 90 minutes, you’ll be guided through a tour of downtown Port Orchard with stops at various historic locations to meet local historians and storytellers as they share bits of Port Orchard’s journey.
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.
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 + Coloring sheets
Stop by the Kitsap Regional Library or the Port Orchard Waterfront Alliance booth (near the foot ferry terminal) for your interactive waterfront scavenger hunt activity and coloring contest sheets.
Family Fun Zone
822 Bay Street
Saturday 1-4pm - Stop by Polaris Theater for chalk drawing, kids ‘fishing’, bubble fun, and a Gilligan’s Island Costume Contest! Dress as your favorite Gilligan’s Castaway character! Winners will be selected at the end of the day. Prizes for adults, kids, and groups.
Love Songs and Ferry Tales
715 Bay Street - salmonberry books
Saturday 3pm - Join Salmonberry Books for two local Author events, ferry merchandise and books available for purchase.
WWCA Fleet Fest Follies
624 Bay Street
Saturday 3pm - Songs and performances from Pirates of Penzance at Western Washington Center for the Arts.
Kitsap Ferries Panel
702 Bay Street (Gathered by Jo’s)
Sunday 3pm - a panel presentation on the history & future of ferries in the Puget Sound with local community leaders like Ed Brown - Head Docent for Virginia V Foundation, 23rd District Rep. Greg Nance, Central Kitsap Commissioner Katie Walters, Maritime Consultant Carla Sawyer, and Steve Sego of Friends of the Fast Ferry, and moderated by Josh Farley.
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.