30+ Things to Do in September on San Juan Island

A September visit to San Juan Island is the very best. The weather is glorious, thanks to the Olympic Rain Shadow. Not only can you experience all Summer adventures, like guided whale & wildlife or sunset kayaking tours, with less crowds, there are also many events just taking place in September (authentic Oktoberfest at the brewery, anyone?). Come on up and savor the San Juans with us this Fall.

1. Fall Foliage Hikes

Treat yourself to stunning island hikes as the foliage turns. Find our Favorite Hikes on San Juan Island here.

2. First Friday Friday Harbor Arts Walk

Meander through the cute coastal town of Friday Harbor and check out the nine galleries in walking distance to the Earthbox Inn & Spa

3. Wine Tasting for Two at Madrone Cellars

Add a wine-tasting-for-two to your room reservation and enjoy the most delicious island-made wine, charcuterie platters and live music on Madrone Cellar’s sunny, outdoor patio in downtown Friday Harbor.

4. Whale Watching Tour

Spot different families of Orca whales, porpoises, Stellar sea lions, Bald Eagles and other seabirds on a guided whale & wildlife tour. And with a little luck, you’ll encounter the majestic Humpbacks in Fall before they migrate to Hawaii for the Winter.

Orca Breaching, Whale Watching on San Juan Island, Washington

5. Free Beach Cruiser Bikes

Take our free-for-guests beach cruisers on a spin. Those are sturdy, one-speed bikes, not meant to replace island transportation, but they sure are fun to take around Friday Harbor and trips to the nearest beach.

6. Sumptuous Oyster Lunch

Head out to the gorgeous Westcott Bay Seafood Farm and treat yourself to freshly shucked oysters, oysters Rockefeller, Oyster po boys, plus other island-made fare and libations while overlooking the farm and water.

7. Bird Walk at the San Juan Sculpture Park

Get inspired at this 20-acre gem packed with sculptures, interactive art and poems along beautiful Westcott Bay. Join local birder Tyler Davis on the first Wednesday of each month at 8:00am for a free bird walk.

8. Try 72 Flavors of Ice Cream

Treat yourself to a cone (or two) from the San Juan Ice Cream Co on the waterfront on your after dinner walk.

Lisette Wolter-McKinley, Friday Harbor, WA

9. Guided Kayak Tour

Explore the serene Salish Sea on one of the last kayaking tours of the season with our friends at San Juan Outfitters in Roche Harbor. Learn about kelp forests and watch for Orcas under the watchful eyes of curious harbor seals.

10. Makers Market at Grange Hall

On Sunday, September 14, 2025, visit the rustic Grange Hall overlooking the waterfront in Friday Harbor and shop for island-made arts and crafts.

San Juan Outdoors - 3 Hour Kayak Tour San Juan Island

11. Safe and Ethical Wildlife Viewing & Photography

Join a National Park Ranger at American Camp National Historical Park every Sunday at noon to learn tips and tricks of stunning wildlife photography while keeping our wildlife wild.

12. Spa Day at the Spa at Earthbox

Take a swim in our sister hotel's indoor heated pool, lounge in the hot tub, and take a sauna before heading over to our cute, onsite spa for a relaxing massage and a rejuvenating facial.

13. Sunset Picnic at the Whale Watching Park

In September the sun sets exactly around dinner time at the renowned Lime Kiln State Park. Get your favorite take-out and head to a waterfront picnic table at one of the best places to see Orcas from land on earth.

14. Romantic Dinner at the Isle’s Original Farm-to-Table Restaurant

Treat yourself to dinner at Duck Soup out in the woods. Indulge in seasonal island-grown fare, handcrafted cocktails and out-of-this-world desserts by the fireplace.

15. Farm Tour Weekend September 26-28, 2025

Celebrate farms, food & community on this self-guided farm tour weekend with tons of kids activities, cider pressing, workshops and of course, delicious food.

16. Volleyball at Jackson Beach

This beautiful little beach in walking distance to downtown has a volleyball net (BYOB – bring your own ball), cooking shelter, picnic tables and a gorgeous hand-carved statue of Tokitae, the Orca who died in captivity in 2023 after spending 53 years in the same tank at the Seaquarium in Florida.

17. Day at the Museums

Visit the stunning Friday Harbor Whale Museum. Meander the outdoor San Juan Historical Museum, and don’t miss the newest powerful PNW exhibition at the Museum of Art, all within walking distance of our Earthbox Inn & Spa.

18. Self-guided Island Tour on a Scoot Coupe from Susie’s Mopeds

Experience the isle from one of the cute scoot coupes at your own pace. Take plenty of dessert breaks and stop to smell the fresh flowers on the roadside stands.

19. Saturday Farmers Market

September farmers markets are bountiful and festive. Enjoy free live music, sumptuous lunch, chair massages, island grown food and crafts.

20. Oktoberfest at San Juan Brewing

Don’t miss the authentic Oktoberfest at San Juan Brewery’s spacious pub on September 27, complete with Festbier and schnitzel, live music, stein-holding and costume contest and other fun games for all ages.

21. Round of Golf

San Juan Golf & Tennis Club, home of the Celebrity Golf Classic, situated on stunning Griffin Bay with views of magnificent Mt. Baker, features a beautifully manicured 9-hole golf course with alternating tee boxes that convert into a long and challenging 18-hole experience. They rent clubs and carts.

22. Explore two National Historical Parks

Vast American Camp and wooded English Camp pay tribute to the last war fought on American soil. Check out the interpretive center, old barracks and gardens and the wildlife on one of the many, awe-inspiring hikes along the coast.

23. Distillery Tasting

San Juan Distillery and Westcott Bay Ciders offer free tastings every Saturday of their award-winning, herb infused spirits and tasty, dry ciders.

24. Horseback Riding

Go on a scenic forest trail or a fun pony ride or take a riding lesson with our friends at Horseshu Ranch.

25. Go See a Play

Have an elegant evening at the San Juan Community Theatre just a few blocks from our hotel. See the newest play, enjoy wine and chocolate during intermission, and take in the newest art exhibition in the fancy foyer.

26. Narrowest Coffee Shop in Washington State

Crow’s Nest Coffee Shoppe is not only the narrowest, but also the best coffee shop in town. Grab a quick bite and an expertly made coffee drink on your way to the beach.

27. Live Music at the Vineyard

Head out to picturesque San Juan Vineyard, a destination winery with an historic schoolhouse and gift shop. Enjoy free, live music and superb wine on Saturday evenings at their tasting room patio.

28. Harvest Winemaker Dinner at Madrone Vineyard - September 7

Enjoy an evening at the cellars and celebrate the local harvest. Sit under 100-year-old heritage apple trees and enjoy dinner by Salmonberry Catering, paired with wines by Madrone. Expect a menu featuring locally sourced and seasonal ingredients, paired with Madrone's newest releases. Reservations are a must.

29. Shopping Spree Friday Harbor

Our small, coastal town’s streets are lined with cute shops and boutiques, bookstores, galleries, bistros and restaurants. Visit the Little Salt Shop for island-made, solar-powered sea salt, honey, salted caramels and other unique island souvenirs.

30. Roche Harbor Mausoleum

Park at the Roche Harbor airport and follow the signs to the mausoleum deep into the woods. The McMillen’s, who owned Roche Harbor and its limekilns, built this impressive mausoleum as a family resting place. Surrounded by gigantic Greek pillars, the mausoleum is laden with freemason symbolism.