ClintonCoupevilleFreelandGreenbankLangleyOak HarborPlacesThings to Do on Whidbey January 15, 2024

A Trip Through Whidbey’s History

Whidbey has history? It must; there are museums here. Compared to any place in Europe it can seem that there’s no real history here; but, Whidbey has had visitors for thousands of years. Follow along with us as we take a trip through Whidbey’s history. 

The island was built from some of the newest geology:

The west coast of North America was originally at Spokane, but tectonic plates moved and eventually some small ones slammed into the continent. That’s where “The Rock” gets its rocks. They hold up our bridge. Further south on the island could arguably be called “The Gravel” because a series of glaciers and ice sheets scraped mountains down to bits. Those bits were dumped into moraines and stream beds that help explain the south end’s hilly roads, as well as some of the slopes that slide.

About 16,900 years ago, those ice sheets finally left. Over 2,000 feet of ice retreated, leaving lands that waited for something to drop by and grow. The plants began to grow providing forests and prairies. The whales, fish, birds, and land creatures arrived. Today you can walk the beach and you may find mammoth teeth and bones (not a joke).

People came soon after:

They didn’t call it Whidbey. One name that became associated with the place was Tscha-kole-chy. Ask the Tulalip tribes or a local historian about how to pronounce it. 

The island became populated just like the rest of the Salish Sea lands. There was food, a good climate, and relative safety from things like volcanoes.

Humans were busy for over ten thousand years, but we have few stories considering how long that period lasted. One good view of that life is the Maiden of Deception Pass sculpture and description

Skip ahead a few thousands of years to when more people started showing up. 

In the late 1700s:

European explorers sailed in. They were to explore the island and discover what existed here, a very natural and human endeavor. Captain Vancouver’s crew named many of the features. The features already had names, but now they had newer names.


Joseph Whidbey circumnavigated the island. Originally, they thought it was a peninsula, but when they completed their counter-clockwise trip and found the pass they were surprised it was an island, hence Deception Pass. 

By 1848:

Some settlers tried settling on the west side of island, near Penn Cove. Thomas Glasgow, Antonio Rabbeson, and A. Carnefix established a farmstead. It didn’t last long. Local tribes were upset in general with settlers throughout the Puget Sound region. The settlers were encouraged to leave, which they did, without even taking many of their tools. 

There was some disagreement between the Spanish, the British, and the pesky Americans as to who owned what. The original inhabitants had their perspective, of course. The various negotiations and treaties are complicated and fascinating. One place to start is with the Pig War on San Juan Island, a seemingly silly disagreement that almost started a real war.

The 1850’s:

Soon after, more settlers arrived. They too saw the value of the forests, farming, and fishing. Coupeville got started in the 1850s, and became the second oldest town in Washington State. The south end towns were quieter; but, Maxwelton had a 3,000 seat auditorium, for a while. The site of Bailey’s store was basically a trading post in the 1850s. Oak Harbor started then, too; and was incorporated in the 1910s.

The island was fractured. There were few roads. The main way to get around was by boat or walking the beaches at low tide. 

It was about this time that Ebey’s tale became history, a fascinating story of someone who regularly rowed to Port Townsend, and then was killed over a misunderstanding. Check out the links at the end of this article if you would like to learn more about this story. 

The next few decades were a bit rough, but profitable for some. Seattle was growing and it became the destination for island food and lumber. Some of the island’s tallest trees became masts for that era’s tall ships. The branches went into the growing steamship fleet’s boilers, as well as into the landfills that became Seattle’s waterfront.

Throughout those decades ships turned from oars or paddles, to sail, to steam, to internal combustion (to electric?).

Ships operated before docks were built. Some ran up onto the beach, got rid of cargo and passengers, picked up more, and backed away before the tide stranded them. A ferry carried people across Deception Pass, before the bridge was built.


The construction of Fort Casey began. After one world war it became obvious that the country needed defenses.  The Navy established its base, and added and shifted as technology changed warfare. Look at the guns at Fort Casey and compare them to the fortifications at Fort Ebey to see a great change in a short time.

Boeing was busy during World War Two, but it was a few decades later that their plant at Paine Field became a major employer. Thanks to the ferries, Whidbey also became a bedroom community.


Meanwhile, after the start of the 20th century, Freeland was started as a place for free land, an experimental community that blended and contrasted socialist and capitalistic principles. Eventually, the culture tended to a more conventional style of community.

In 1919:

Ferries began docking at docks on south Whidbey, not just running up on beaches, and it became possible to ferry cars and trucks onto the island. They probably had wait lines and cancellations, too.

In 1920:

Langley became one of the first cities in America to have an all-women government. They inaugurated a series of reforms that cleaned up the town, literally. 

About that time, some of the other rough edges of Whidbey were softened as artists began using the island as a retreat and refuge. 

Thanks to fishing resorts, Whidbey was already gaining a reputation as a place to get away from The Big City of Seattle. Tourism got a beachhead.

It became obvious to some that Whidbey’s relationship with Seattle could be like the East Coast’s tourist towns relationship between cities like New York and the Hamptons. That tourist traffic became yet another reason to justify the Deception Pass Bridge.

Life in general became easier as the entire island was finally connected with roads and power.


By the end of the 90s, Whidbey was already known for its various communities: farming, the arts, for tourists, for commuters, and for retirees. Currently, it is being redefined again as Whidbey’s rise from obscurity has grown into an international destination for tourism and training. 

What’s next? Being remote is redefining itself. Whidbey Island is being ‘found’. De-urbanization means urban dwellers are trading that lifestyle for something quieter and slower with a bit more room. But, what’s really next? That’s what every resident and visitor and fan gets to help redefine. History never ends. Welcome to this chapter, the one that you are in. What history will you create?

Connect with us whether you already live here, visit often, or want to move here. 

Destination WhidbeyNeighborhoodsOak HarborPlaces January 17, 2022

Maylor Point

In this amazing shot by Willie Shaw at Team Shaw Photography, you can see the actual harbor of Oak Harbor, the marina, Maylor Point with its iconic white radar dome, the spit to Polnell Point, and the snow-covered Cascade Mountains. Phenomenal views like this one can be seen while driving all over Whidbey Island. Winter makes these vistas even more stunning by providing clear air and snow-capped mountains in every direction. This is just one of the reasons a drive down the length of Whidbey is designated as an official scenic byway called the “Whidbey Scenic Isle Way”.


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CoupevilleDestination Whidbey January 3, 2022

Fort Ebey Fort

Treading toward the pinhole of light at the end of the dark tunnel, you hear the creak of an old metal door as it’s caught by a slight breeze. Your steadiness escapes you as you break into a firm sprint until your eyes see the safety of the trees and vista. It’s hard to keep your imagination at bay when visiting Fort Ebey’s eerie bunkers. Built in 1942 as part of the coastal defense system for World War II, Fort Ebey was home to a state-of-the-art battery with two 6-inch guns. When its usefulness ran out, the property was purchased by the state who chose to keep elements of the old battery when opening up the park, making it possible for thousands to explore and enjoy these thrilling bunkers every year.


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Destination WhidbeyLangleyPlacesThings to Do on Whidbey December 20, 2021

Goss Lake Langley

Located between Freeland and Langley on the southern end of Whidbey, Goss Lake is the perfect spot for relaxing and taking in the fresh PNW air. Enjoy the beautiful greenery and waterfront view with a hike around Goss Lake Loop or (on the warmer days) take a dip in the freshwaters. During the colder seasons, break out the fishing gear and catch some native coastal cutthroat trout. With only one public access point and no motors permitted except for electric, this location remains the perfect oasis for a quiet afternoon. Yet during the annual Whidbey Island Triathlon, this lake gets some extra activity as the location of the event’s swimming leg.


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CoupevilleDestination WhidbeyThings to Do on Whidbey December 6, 2021

Ebey’s Landing

In 1850, local history was made on the shores of Whidbey Island when Isaac Ebey landed on a rocky westside beach and became the first official white settler on the island. With an entire island to choose from, Ebey couldn’t have done much better than the pristine pastureland of what is now known as Ebey’s Landing. This brilliant landscape is situated right at the southwestern side of Coupeville and features breathtaking views of Puget Sound and the Olympic Mountain range. The landing’s soft rolling hills blanketed in rich soil—perfect for cultivating crops—was this area’s true draw to its original settler. Today this landscape remains largely unchanged from the early days of settlers thanks to Ebey’s Landing Reserve. It’s the perfect place for a long walk to get lost in the life of the past.


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Things to Do on Whidbey September 14, 2021

Must Watch Movies and Shows Filmed on Whidbey


Real EstateStats July 16, 2021

Monthly Stats: June 2021

Market Trends, whidbey Island

Destination WhidbeyGreenbankNeighborhoodsPlacesThings to Do on Whidbey July 12, 2021

Greenbank Farm

In the early 1900s, the Greenbank Farm in Greenbank was used to harvest trees and maintain a dairy herd. The main barn you see today dates back to 1904. By the 1940s the farm was sold to John Molz who began loganberry farming. By 1970 it was the largest Loganberry farm in the US. Later it was sold to Chateau Ste. Michelle who planned to sell the 522 acres for residential development. Luckily in 1997 the Port of Coupeville, Nature Conservatory, and Island County combined forces and purchased the Farm for public use.

Today, this picture-perfect farm features dog-friendly walking trails, demonstration gardens, solar power demonstrations, wetlands, wildlife, several shops, and art galleries. One of our favorites is the Whidbey Pie Cafe that brings tribute to the history of the farm with their loganberry pie among many other delicious choices.

Check out the rest of Whidbey’s beautiful destinations from this series here.

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NeighborhoodsOak HarborReal Estate May 11, 2021

5 Most Affordable Neighborhoods Near Oak Harbor & NAS Whidbey

Watching today’s housing market is like reliving a supply and demand lesson straight out of your High School Macroeconomics class. Home prices continue to rise due to the sheer lack of homes for sale on Whidbey Island. Especially in the lower price points $400,000 and below.

Here are 5 of the most affordable neighborhoods within 10 miles of downtown Oak Harbor and NAS Whidbey.

#1 City of Oak Harbor:

Median Price Point as of this post = $318,000 (15.6% increase from last year). Because Oak Harbor has been developed over the decades by various builders at different rates there are a lot of little neighborhoods. The most affordable area can be found in the middle of the City, on the East side between Highway 20 and SE Regatta Dr. Most homes in this area are from the 1950s in developments like Patton’s Pasture & Shady Oaks.

City of Oak Harbor

Design by Windermere Whidbey Island

#2 Rolling Hills:

Median Price Point as of this post = $338,500 (16.9% increase from last year). Located between Oak Harbor and Coupeville Rolling Hills was incorporated in 1961 but you will find a broad range of homes built across the decades. There are many manufactured homes, a few mobile homes and lots of stick built. One of the unique features of this community for Whidbey Island is their Community facilities which includes a pool, clubhouse, basketball court, baseball field, picnic shelter, and even some waterfront with a private pier. Water is managed by the community. All the homes are on septic systems, some with a community drain field.

Want to learn more about Rolling Hills? Click here. 

Rolling hills







Median Sales Price for Rolling Hills by Windermere Whidbey Island

#3 Penn Cove Park:

Median Price Point as of this post = $348,500 (12.2% increase from last year). Although Penn Cove Park now connects to Cove View Circle, has several water view homes, and has a new construction project going on nearby we are going to focus on the original homes built for this neighborhood that don’t have water views, because this is the more affordable area. Homes were built mostly between 1950-1980, all are 1-story. All are connected to a very rare, combined sewage treatment plant (not on septic) managed by Penn Cove Water & Sewer. This best part of this neighborhood is the location. One of the most enjoyable beaches with a low slope and sandy areas and public boat launches is right at the end of Monroe Landing. You can look across Penn Cove and enjoy views of the seaside Town of Coupeville and its iconic wharf.  Conveniently located between Oak Harbor and Coupeville you have access to two very different types of commerce and can petition to be in either school district.

Penn Cove



Median Sales Price for Penn Cove by Windermere Whidbey Island

#4 Northgate Terrace:

Median Price Point as of this post = $295,000 (15.8% increase from last year). Most of this community was first developed in the late 70’s. It is a mix of manufactured and smaller stick-built homes. There is a homeowner’s association, water is managed as a community by King water and there is a community clubhouse you can rent for gatherings. It is conveniently located right off of Highway 20 between the City of Oak Harbor and Deception Pass Bridge. More information can be found on their community web site here.

Northgate Terrace

Median Sales Price for Northgate Terrace by Windermere Whidbey Island

#5 Deception Park View:

It may be a tiny little neighborhood but it’s a delight and as you can see from their website they really care about their little community. It has a very active Homeowners Association. You can learn all about their recent efforts to create a Community Recreation Area in the neighborhood on their website here.

Deception Park

Median Sales Price for Deception Park by Windermere Whidbey Island

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CoupevilleDestination WhidbeyNeighborhoodsPlaces May 10, 2021

Coupeville Wharf

Several small wharfs once reached into Penn Cove only able to be used during very high tide. In 1905 the Coupeville Wharf was built, extending 500 feet to accommodate the increase in commerce due to the activation of Fort Casey. Often referred to as the “Old Grain Wharf”, had an important job to do. It was the key to the distribution and storage of grain grown on our local farms, as well as, bringing goods to the island.

Today, the wharf is home to a gift shop, restaurant, coffee shop, restrooms, naturalist display, kayak rentals, and more! It can be a long 500-foot walk to the end, but chances are high of seeing an eagle, fish, jellyfish, sea star, or sea anemones in addition to beautiful water and mountain views.  Kayakers and boaters love making a stop at the Coupeville Wharf. It is a picturesque icon and hopefully, it will stay that way for another 100+ years!

Check out the rest of Whidbey’s beautiful destinations from this series here.

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