The Whidbey Island Area Fair is an annual showcase for livestock, crops, farm animals, homemade crafts, and just general entertainment with live music, food, competitions, and more.

Wag'n'Walk is an annual fundraising event for the Whidbey Animals' Improvement Foundation with fun activities like shows, contests, and games for dogs and people.

The Whidbey Island Kite Festival is a two-day celebration for kite lovers put on by the Whidbey Island Kite Fliers club each year. Beyond many different kinds of kites being shown off, there are individual and team sportkite competitions, kitemaking for kids, and beginner sportkite lessons.

Langley's Mystery Weekend is one of the longest running annual events of its kind. The whole town, including the many tourists who come just for this, are notified of a crime and must spend the weekend attempting to solve it.

The Penn Cove Mussel Festival takes place over a weekend in March and is centered around events like the mussel eating competition, chowder tastings, restaurant hopping to try different mussel recipes. Puget Sound has naturally high concentrations of mussels as it is a nearly perfect environment for them to grow; visitors can also take a tour of the mussel "farm".

The Loganberry Festival is held annually at Greenbank Farm and is a melting pot of agriculture, music, and animal events. Activities range from dog and equestrian shows, falconry exhibitions, pie-eating contests, live local music, regional vendors, and art on display by local artists.

The Choochokum Music and Arts Festival features original music by mostly local performers across 3 stages and two days, complete with a street fair filled with arts and crafts vendors and a traditional Saturday night street dance.

Tour de Whidbey is an annual bike race and simultaneous tour of some of Whidbey Island's most scenic views, all to benefit the Whidbey General Hospital. There are 6 different routes from 10-100 miles long of varying difficulty for all skill levels.

Whidbey Island Race Week is a competitive, 5-day keelboat race featuring nearly 200 participants. Awards ceremonies and entertainment such as live music and recreational activities are held nightly.

Greenbank Car Show- This annual event features hot rods, collectibles, antiques, racecars, and custom-made cars, including a rare 1929 Ford Towncar- there are only 18 left in the world! Visitors can vote for their favorite car to win the "people's choice" award.

The Whidbey Island Scenic Isle Way was Washington's first island designated as a scenic byway, and it was for a good reason. This is a short road trip with many opportunities for stopping to picnic or shop in town, or just get out of the car and enjoy the spectacular views from Deception Pass or the town of Oak Harbor.

The Island Shakespeare Festival strives to offer the community free, classic, and great Shakespeare theatre. Previous shows have always taken place in the woods, but recently the group has acquired a custom built 2,400 square foot tent to perform, still outdoors, but out of the unpredictable Northwest weather.

The Whidbey Island Center for the Arts promotes visual arts, dance, music, literature, and quality theatre within the community by putting on several performances each month, including plays such as "You're a Good Man, Charlie Brown" and the classical music of Mozart and Vivaldi performed in the Island Consort Chamber Series.

The Whidbey Playhouse has been performing live theatre for Oak Harbor since 1966. Their productions range across almost all genres, including musicals, comedies, improv, dramas, and youth productions. Previous shows have included "A Midsummer's Night Dream", "Joseph and the Amazing Technicolor Dreamcoat" and shows by the Whidbey Improv Team, in addition to many others.