August Favorites on San Juan Island

Temperate San Juan Island is not only the perfect place to escape the Summer heat and the best place to see Orca whales in the wild, it is also brimming with unique, often free, art, music and community events.

Treat yourself to Summer on San Juan Island this year. Lounge in our comfy pool patio by the coffee shop, get pampered at our spa, walk to all the shops, restaurants and summer markets from our Friday Harbor hotel and explore the countless outdoor adventures San Juan Island offers.

San Juan Summer Arts Festival – August 9 & 10, 2025

Enjoy San Juan’s arts and crafts, live music, local libations and kids activities at this fun fest in downtown Friday Harbor.

San Juan County Fair – August 14-17, 2025

Delight in an authentic small town county fair in walking distance to the Earthbox Inn & Spa and browse local vendors, delicious food, carnival rides, 4-H animals, community events and dance to live music until late into the night.

Theater under the Stars – July 24-August 17, 2025

Acclaimed Island Stage Left presents “The Drawer Boy” by Michael Healey this Summer. The Drawer Boy is about the power of storytelling in creating and interpreting reality and how it can transform lives. Thursdays through Sundays at 8:00pm at the Island Stage Left outdoor stage on Wold Road. Admission is FREE! Donations appreciated. Bring a blanket & dress warmly! No latecomers, please.

Up Up Crane Truck Circus – August 19

Come out to the gorgeous former lavender farm and enjoy this outdoor circus show of aerialists, musicians, clowns, and illusionists with whimsy, beauty, and hilarity, accessible to audiences of all ages. With a flatbed truck, a baby grand piano for live music, and a mounted 30' hand cranked crane, Up Up brings giggles, gasps and delight to audiences from all walks of life.

Live Outdoor Music

Head to San Juan Brewing or the picturesque San Juan Vineyard for free, live music on Saturday nights. Bring a blanket and a picnic to the fabulous outdoor Historical Museum for free Music on the Lawn on Wednesdays or immerse yourself in the Lakedale Jazz Festival on August 22 & 23.

Float Fest – August 30 & 31, 2025

This joyful Summer event at beautiful Roche Harbor resort, with an amazing artist line up, great food and superb floating devices is benefitting San Juan Island’s Community Cancer Fund. Enjoy a fun-filled weekend by the water while making a meaningful difference.