Whidbey Island November 29, 2023

Holiday Events on Whidbey Island WA- Celebrating The 2023 Holiday Season

Whidbey Island and Oak Harbor, Washington have vibrant communities that organize many festivals and events over the winter holiday season. Whether you’re just visiting for the holidays, you live there now, or planning to move to Oak Harbor, we’re sure you’ll find at least a few fun 2023 events to experience this holiday season.


 holiday calendar with snowman - holiday season on Whidbey Island

What’s There To Do on Whidbey Island for Christmas?

If you’re looking to fill your shopping and social calendar for the holidays, there are plenty of exciting holiday events and fundraisers throughout Whidbey Island. We’ve looked up the events happening in 2023. Add them to your calendar now so you don’t miss these exciting local events:

Oak Harbor Christmas Events

Green Ticket Cash Giveaway

Green Ticket Cash Giveaway

Dates: November 1 – December 15, 2023
Get rewarded for shopping locally. Earn a green ticket for every $20 purchase at participating Oak Harbor merchants. Your tickets could win you a cash prize of up to $1,500 (Cash prizes are $1500, $500, two $250, or five $100).

A big shout out to Heritage bank for sponsoring.


Main Street Holiday Market

Dates: Weekends between November 11 and December 17, 2023


Get your holiday shopping done at the annual Main Street Holiday Market. You’ll get to meet and shop with many local artisans and crafters. Be sure to stop by on Dec 2 for the Home for the Holidays Parade and tree lighting ceremony).


2023 Santa Parade & Tree Lighting Date: December 2, 4:00 – 6:30 pm, 2023


Bring the whole family to watch Santa in the Oak Harbor Santa Parade on Pioneer Way (starting at 4 pm). The tree lighting ceremony begins at 5:15 pm at Dock and Pioneer. End your evening with carolling at Whidbey Playhouse after the tree lighting. 

Wreath-Making Workshop

Dates: December 1 and 3, 2023

Get expert instruction on how to make and customize your holiday wreath. Bring your family or friends and enjoy wreath making, drinks, and light snacks. All supplies included. 

Big Brothers and Sisters of Island Country holiday events

This local organization is hosting three special 2023 Christmas events:

  • Festival of Trees – Gala and Live Auction
    Date: December 1, 5:00 – 10:00 pm
    Enjoy an elegant evening and charity fundraiser at this 21+ Gala at the Oak Harbor Elks Lodge.
  • Mingle with Kringle
    Date: December 2, 6:00 – 10:00 pm
    Enjoy a casual evening and fundraiser with cocktails, light snacks, and holiday fun at this 21+ event at the Oak Harbor Elks Lodge.

Bring the whole family (including your teddy) for a festive breakfast and fundraiser. Bring an extra teddy bear or stuffed animal to donate to a child in crisis. 

Coupeville holiday festivals and events

Red Ticket Cash Giveaway

Dates: November 15 – December 17, 2023


Whidbey Island Holiday Events

Get rewarded for shopping locally. Earn a red ticket for every $20 purchase at participating Coupeville merchants. Your tickets could win you a cash prize at the draw on Dec 17 at the Island County Historical Museum (1 pm).


Light up your Holiday

Date: December 9, 4:00 – 7:00 pm, 2023

Head to the Admiralty Head Lighthouse on Dec 9 for a fun and magical evening, with Santa pictures, music, games, marshmallow roasting, and festive lights on the lighthouse. 


Greening of Coupeville

Date: December 2, 4:00 – 6:00 pm, 2023

Watch the annual holiday parade down Main Street up to the library. Look for a jolly special guest at the end of the parade. End your evening with carolling at Cook’s Corner Park.


Captain Whidbey Tree Lighting

Date: December 1, 7:00 – 9:00 pm, 2023


Visit the Captain Whidbey Inn in Coupeville for a cozy, laid-back evening with friends and family, warm drinks, and the beautiful holiday lights in the lobby. 


A Very Merry Whidbey Christmas

Date: December 16, 2:00 – 4:00 pm, 2023


Join the Whidby Saratoga Orchestra at the Coupeville High School for a special performance of a Very Merry Whidby Christmas. 


Friends of the Coupeville Library Annual Gingerbread Challenge

Date: November 25, 10:00 am – 3:00 pm, 2023


Pick up a gingerbread-making kit (only 30 available) and design your best gingerbread house. See all the entries at the Coupeville library between Nov 25 and Dec 16, and stay tuned for the winner announcement on December 17. 

Whidbey Island Holiday Events

Christmas Things to do in Greenbank 

2023 Makers Boutique

Dates: Nov 3/4 and 17/18, 10 am – 4 pm, 2023


Shop from local artisans and crafters during this 2-weekend event. Come to the market, get your holiday shopping done, and buy some treasures and goodies for yourself, too. 

2023 Greenbank Farm Holiday Market

Dates: Dec 3/4 and 11/12, 11 am – 4 pm, 2023


The 2023 Greenbank Farm Holiday Market is being run by the Port of Coupeville.

Whidbey Island Holiday Events

Holiday Happenings in Freeland

A Celtic Christmas with the Beggar Boys

Date: December 9, 3:00 – 5:00 pm, 2023

Get tickets for an evening of song and storytelling at St. Augustine’s in-the-woods. Enjoy traditional Christmas music from Ireland, Scotland, and Wales with the Beggar Boys. 

Clinton holiday community events

Holiday Market in Clinton

Dates: December 2 and 3, 2023


Stop by the Clinton Community Hall to shop with 25 vendors, eat holiday treats, and visit with your favorite jolly man (Santa arrives at 11:00 am both days). 


Spending the holidays in Langley

Holidays by the Sea 2023

Dates: Throughout November and December

Grab your seat early for the annual Jolly Holly Parade (noon), then check out the lighting ceremony at Langley Park on December 2 from 2:00 to 5:00 pm. 

Whidbey Island Holiday Events

County Christmas at the Fair

Dates: November 24-26 and December 1-3, 9:00 am to 4:00 pm, 2023


Join your neighbors at the Fairgrounds for a 2-weekend holiday market. Sales support local merchants, and partial proceeds go towards the Island County Fair Association to support scholarships for local youth. 


“The Nutcracker” by the Whidbey Island Dance Theatre

Dates: December 8-10 and 15-17, 2023


Join the Whidbey Island Dance Theater for its 31st annual Nutcracker performance at the South Whidbey High School Auditorium.


Holiday concert with the Whidbey Orchestra

Dates: December 15 and 17, 2023


Get in the holiday spirit with a holiday concert conducted by Cynthia Morrow. The December 15 concert will be at Trinity Lutheran Church, and December 17th will be at the Island Church of Langley.


Winter Wonderland Market

Dates: November 25 and December 2 and 9, 10:00 am – 3:00 pm, 2023


Eat, shop, and be merry at the Bayview Farmers Market Holiday market. Dress warm, as some vendors are outdoors. 

Whidbey Island Holiday Events



About Whidbey Island and Oak Harbor, Washington

The Better Homes and Gardens McKenzie Realty team are experts in Whidbey Island communities and real estate, including Oak Harbor and South Whidbey Island. We can help you learn about the community, including special holiday happenings, so you can learn more about what life is like on the island. We also proudly participate in the Homes for Heroes Program, donating over $2 million from our commissions to this worthy cause.


Contact our team today to begin your Whidbey Island and Oak Harbor home search.


And Happy Holidays from the entire McKenzie Realty family to yours!