11 Festive Things to Do on Whidbey Island in the Fall
Looking for fall activities on Whidbey Island, WA?
Fall on Whidbey Island is more than just pumpkin spice and crunchy leaves. Living here, I get to see firsthand how the island leans into the season with festivals, sunflower fields, haunted mazes, and a few quirky traditions you won’t find anywhere else.
If you’re a fan of Practical Magic, historic Coupeville doubled as the backdrop for this seasonal cult classic and the town takes full advantage of it.
Without further ado, here are 11 fun fall things to do on Whidbey.
Coupeville
1. Scenic Isle Farm
The Sherman family has been farming the land at Scenic Isle Farm for five generations and they’ve embraced fall celebrations in two stages.
Sunflower Stroll
Aug 9-Sept 1, 2025
If you swing by in late summer, you’ll catch their Sunflower Stroll. The field is a-bloom with an array of fresh golden flowers to ones just starting to go to seed.
Wander through acres of trails through these towering flowers. Little resting spots are peppered throughout, tucked between the stalks.
You’ll eventually find your way to a big open clearing in the middle, a perfect place to bring a picnic, play some lawn games, or just relax amongst the blooms.
You’re welcome to pick a stem to take home (included in admission) or buy a full bouquet at the farm stand.
Pumpkin Patch
Oct 1-31, 2025
Scenic Isle Farm is the only official pumpkin patch farm on Whidbey Island. The pumpkin patch stretches across seven acres, and you can hop on a trolley ride to get out there.
Elsewhere on the farm are family friendly activities scattered throughout.
There is also a Haunted Barn and Sunflower Spook trails, utilizing the skeletal remains of the sunflower fields from the month before.
If you don’t feel like picking your own pumpkin, piles of pumpkins in every shape and size are available for purchase at the stand.
🐕 Dogs are welcome on the farm, as long as they stay on a short leash.
2. Scarecrow Tour
1st weekend of Oct-1st weekend of Nov
Coupeville goes all out with its annual Scarecrow Tour. Each year brings a new theme, and for 2025 they’re doing Scooby Doo.
Local businesses, nonprofits, and community groups compete to create the best scarecrow display, each one set up around town.
I like picking up a map of all the scarecrow locations from the Chamber of Commerce or the Coupeville Library and then voting for my favorite scarecrow!
3. Practical Magic Movie Night
Oct 23-25, 2025
Celebrate Practical Magic at the Central Whidbey Chamber of Commerce in Coupeville, the very town where this cult classic was filmed. (Confession: I don’t get the hype 😬)
Compete for prizes in a costume contest in your best witch outfit or as your favorite Practical Magic character.
Test your Practical Magic knowledge with trivia and learn some behind-the-scenes stories.
The bartenders will be mixing up Midnight Margaritas alongside beer, wine, and non-alcoholic options.
Complimentary popcorn flows throughout the night and the movie begins at 8 pm.
This is a 21+ event.
4. Torchlight Parade & Street Dance
Oct 25, 2025
Enjoy a night of community fun on historic Front Street in Coupeville. Dress up in your best costume and join the Torchlight Parade, where local businesses and organizations hand out candy along the route.
The parade makes its way down to the Coupeville Wharf, the town’s most iconic landmark.
Afterwards, the party continues with DJ Moose keeping the energy going for a lively street dance.
5. The Great Coupeville Pumpkin Race
Oct 26, 2025
Rev up your gourds for one of Coupeville’s quirkiest fall traditions. The Great Coupeville Pumpkin Race is open to all ages and brings equal parts competition and comedy to the streets of town.
There are two racing categories, so you can decide how serious you want to be.
Iron Gourd is for the dedicated racers who follow the official Pumpkin Race rules to a T. Pumpkin are judged on precision and speed, and the Grim Reaper himself shows up to make sure the standards are met.
Pumpkin Pandemonium is all about chaos and creativity. This is where anything goes, from wild pumpkin designs to wacky contraptions. It’s less about winning and more about putting on a show.
The action happens on NW Coveland Street by Town Park in Coupeville, where the whole community gathers to cheer on pumpkins as they roll, wobble, or crash their way toward the finish line.
6. Coupeville Harvest Fair
Oct 11, 2025
The Coupeville Farmers Market’s season closes with their annual Harvest Fair.
Located behind the Coupeville Public Library, the market will feature all the vendors you’ve seen all year along with a festive fall celebration.
You’ll find a haybale maze, pumpkin patch, penny carnival, live music, and food vendors.
Keep an eye out for seasonal flavored items to eat around the island too! Coffee shops like Cedar and Salt make their own real pumpkin spice lattes and Chris’ Bakery menu flavors change monthly so you could find items like pumpkin flavored donuts.
Greenbank
6. Harvest Faire
Sept 6, 2025
Harvest Faire is held at Greenbank Farm and is quite the autumn gathering.
The day is filled with good ol’ fashioned fun: hayrides, egg tosses, egg spoon races, and even a pie eating contest.
I couldn’t believe how many lawn games there were to keep kids entertained. They also have free crafts to release their creative juices and a chance to meet farm animals.
There’s live music by local artists, food trucks so you don’t go hungry, and a beer garden for the grown-ups.
Stroll the quaint gardens, hike the trails with your dog off leash, or spend some time shopping for antiques and vintage clothing.
7. Whidbey Island Cider Festival
Sept 20, 2025
The Whidbey Island Cider Festival is a full fall day spent tasting not just local ciders but also beer, wine, mead, and spirits poured by local makers.
The festival, hosted at the Pacific Rim Institute for Environmental Stewardship, goes beyond just drinking.
Local musicians are scheduled to play throughout the day, including my favorite, Kick Brass.
There’ll be plenty of food trucks to keep you satiated serving up everything from sweet treats to savory plates.
Learn about different varieties of apples and watch a cider press in action.
Shop for new greenery at the native plant nursery.
If you want to take a break from the festival grounds, there are over two miles of trails to wander.
While General Admission is free, “Drinking” Admission for 21+ is paid and includes a keepsake tasting glass with the festival logo and six tasting tokens.
8. Greenbank Oktoberfest
Oct 4, 2025
Dust off your dirndl and lederhosen for Oktoberfest at Greenbank Farm. This 21+ event brings the best of Bavaria to Whidbey with local handcrafted beers and cider, plus traditional German brews shipped in straight from Munich.
Live Bavarian music will grace your ears as you eat classic foods like brats, sausages, pretzels and more.
You’re gonna wanna come for the games! Test your strength in the Masskrugstemmen liter stein lifting or your aim in the Nagelbalken nail-hitting challenge.
There’s also the Saratoga Sausage Toss (think egg toss with sausages) and the Biermarionette, where you maneuver strings to lift a glass of beer to your mouth without spilling.
Some games require teams, so bring friends!
Own a dachshund? Enter them in the Weiner Dog Race to compete against fellow short legged canines!
Entry requires a general admission ticket, plus separate purchases for drinks and event participation.
Oak Harbor
9. K & R Farm Stand
K & R Farm Stand is open from spring to autumn, but the biggest fall attraction here is their big sunflower field, perfect for snagging seasonal photos.
The farm stand itself is stocked with in-season produce sourced locally and around the state and shelves lined with jars of sauces and jams.
One of the biggest draws for families is the ice cream. They scoop up 32 flavors of Pacific Northwest ice cream in freshly made waffle cones.
If you’re craving something different, they also serve shave ice that’ll give you a little taste of Hawaii right here on Whidbey.
The lawn is dotted with picnic tables and a few lawn games, making it an easy rest stop while you’re out exploring the island.
And thanks to its location near NAS Whidbey, you might even catch a fighter jet landing overhead.
10. Harvest at the Harbor
Sept 13, 2025
The city of Oak Harbor welcomes in autumn right on the water with Harvest at the Harbor at the Oak Harbor Marina.
This free event is family friendly and oriented. Kids can join in themed crafts and games, or sign up for the build-a-boat Rain Gutter Regatta for a chance to win decent prizes donated by local businesses.
There’s also a scavenger hunt, tractor photo booth, and facepainting.
Boat tours are given to those curious about who’s parked at the marina.
Local vendors set up by the gazebo, selling everything from handmade jewelry to home decor and everything in between and food trucks set up shop to feed hungry attendees
10. Whidbey Farm & Market
Sept 19-Oct 31, 2025
Whidbey Farm & Market is my favorite farm on the island and is the epitome of community farm fun just outside of Oak Harbor.
Think corn maze, hayrides, barrel train rides, a hay bale pyramid with a slide, photo ops, and pick your own corn and potatoes.
There are a variety of events happening throughout the season as well.
Corn Fest
Sept 20–21, 2025
Serving up fresh-grilled corn and live music, Corn Fest kicks off the fall season on the farm.
On the 20th, round up a partner for the free Cornhole Tournament and see if your “a-maize-ing” toss skills will win you prizes.
Alice in Wonderland Scarecrow Competition
Local clubs, squadrons, and community groups are invited to bring Wonderland to life with their own themed scarecrows to compete for prizes.
Once displayed on the farm by Sept 27th, you can vote online or in-person for your favorite scarecrow.
Pumpkin Carving Contest
Oct 11, 2025
How are your pumpkin carving skills? Put them to the test by competing in this free contest.
Haunted Maze
Oct 24, 25, and 31, 2025
By day, the corn maze is safe, but by night, you better watch out lol!
This year’s haunted maze takes you “Down the Rabbit Hole.” Are you brave enough to face what lurks inside by night?
Trunk or Treat
Oct 31, 2025
End the season with a safe trick-or-treating event. Decorated car trunks, candy, festive farm fun, and photo ops make it a perfect family night. Free and open to all ages.
🛏️ Where to Stay on Whidbey Island
If you’re looking to make a fall weekend getaway to the island, here’s a couple places I suggest:
For Romantics: Captain Whidbey – historic inn on Penn Cove combining luxury with comfort
For Character: Auld Holland Inn – Dutch architecture motel with home rooms and free breakfast
Whidbey Island really knows how to make the most of fall and there’s no shortage of ways to soak in the season. Pick a weekend, grab your coziest sweater, and head to the island—you’ll find fall fun waiting around every corner.
If you’re looking for more pumpkin patch options, check out all the farms in Snohomish!
