Top 2021 Fall and Winter Activities on San Juan Island

by | Oct 28, 2021 | Blog, Events | 0 comments

Fall and Winter on San Juan Island are full of magic: the changing leaves, the smaller crowds, the beautiful stillness that doesn’t always exist during other seasons. It’s not only a great time to visit us at Lakedale, but also the perfect opportunity to spend a good chunk of time on San Juan Island—there are some really wonderful activities going on, most of which are annual. We’ve broken them out chronologically by season, so take note, and start planning ahead. Also be aware that if you’re traveling by ferry to San Juan Island, the winter sailing schedule is slightly more limited and ferry wait times, given staffing issues, are longer. Bring a book, some snacks, and maybe a few games. You’ll be glad you did!

Additionally, another pro tip about the ferry: check the sailing schedule as soon as you begin planning your trip. Don’t sleep on making a reservation both ways (trust us), even though the crowds are lighter. If you’re choosing another way to get to San Juan Island (airplane, seaplane), keep in mind winter weather is often at least partially overcast. Pack layers, keep a pulse on the weather, and use these Fall and Winter activities on San Juan Island as a foundation for planning your trip:


Farmers Market (May through October)

The San Juan Island Farmers Market at Brickworks runs Saturdays through October, which is a longer timeframe than many other farmers markets in the Pacific Northwest. You’ll find produce, wares, art, crafts, and many other goodies from the market’s 35(ish) vendors. It provides an outlet for agricultural products that are grown, harvested, or processed in San Juan County, too. Stock up on all the items you need to make a beautiful meal back at Lakedale, or grab a snack to go while you stroll around Friday Harbor. 

Farm on San Juan Island

Farm Tours (September)

September farm tours cover San Juan Island, Orcas Island, and Lopez Island. The San Juan Island-specific tours celebrate farms, food, and community. They include free farm visits, events, education, and family fun. Check out the 2021 brochure to get a sense of what the three-day event included and to see what to expect in 2022. 

Film Festival (October)

The Friday Harbor Film Festival is a community-organized annual festival with volunteers who combine their efforts to bring viewers the best in documentary film entertainment. Similar to 2020’s event, the 2021 festival was virtual, although it’s been in-person historically. Keep an eye on their website for updates on what you’ll see in 2022. 

Friday Harbor Scarecrow Festival

Friday Harbor Scarecrow Festival (October)

Wander the streets of Friday Harbor and enjoy the scarecrows created by local businesses. We are an artists’ haven, so the creativity in this second annual event is unmatched. Scarecrows will be on display from October 15 through at least October 28 and you’ll be able to vote on your favorites from October 20-28. All proceeds benefit the Friends of the San Juan Island Library. 


Island Artisans Holiday Market (November)

Over Thanksgiving weekend, the Island Artisans Holiday Market fundraiser will be held at the San Juan Island fairgrounds. 50+ artists, craftspeople and food vendors gather together to show and sell their wares. 10% of proceeds will be donated to the Artists to Island Artisans, a 501 3(c) nonprofit group. 

holiday lights in Friday Harbor

Island Lights Festival (November – December)

Enjoy the twinkling holiday lights in Friday Harbor starting in November and running through December. If you’ve never walked through town during this time, it’s a magical bucket list item that will make your holidays that much more joyful. Gaze up at trees encircled with lights while you warm your hands around a cup of warm cocoa or cider. Keep your eye on the website for more information and specific dates. 

Christmas Fair on San Juan Island

Christmas Market (December)

Just like the San Juan Island farmers market, the Christmas Market will be at Brickworks again this year. Spanning two days (December 10-11), the popular event will play host to a holiday crafts market, island food vendors, local farm products, live music, local libations, and activities for kids and grownups alike. Enjoy the festivities on Friday, December 10, between 10 a.m. – 7 p.m. and on Saturday, December 11, from 10 a.m. – 3 p.m.

Also, keep your eyes peeled for more information about Winterfest, an annual island celebration that includes a tree lighting at Memorial Park, an old-fashioned Christmas market, a holiday concert, and more! Hundreds of people gather to drink hot cider and watch as the two Dutch Elm trees in Friday Harbor illuminate the waterfront, while carolers ring in the holiday season.

In addition to all these scheduled activities, there are many easy hikes around the island that are particularly serene and picturesque in the fall and winter: English Camp, American Camp, and Cattle Point Lighthouse are just a few. You can also island hop via inter-island ferry or seaplane, stroll through the Sculpture Park, linger over dinner, or stay in with a bottle of champagne in one of our Lodge rooms (check out our Specials page for more on that). 

Fall on the lake at Lakedale



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4313 Roche Harbor Rd,
Friday Harbor, WA