Top 20 Washington State Trips

Oak Harbor WA

Oak Harbor is at the north end of Whidbey Island in Washington State. It's the largest town on Whidbey Island, with a population of roughly 24,000 people. Oak Harbor isn't as popular as the smaller towns of Langley and Coupeville, but it still has some gems worth visiting.

Oak Harbor’s main street is known as Pioneer Way, and is one block from the harbor.  From here it’s a short walk to the waterfront boardwalk, and the popular Windjammer Park with a beach, playground, and splash-pad.

There are other fun attractions at Oak Harbor, like a retro drive-in theater, vintage roller skating barn, and excellent naval museum.

History:  Oak Harbor was founded in 1851, settled by Irish sea captains in the 1850s and Dutch farmers in the 1890s, who took advantage of the busy maritime commerce. Many of Oak Harbor’s streets have Dutch and Irish names.

Oak Harbor transformed from rural town to city when the Deception Pass Bridge opened in 1935, followed by an influx of personnel with the arrival of the Naval Air Station Whidbey Island in 1942. This was the largest naval base in the Pacific Northwest, and displaced many of the historic Dutch farms and windmills.

10 best things to do at Oak Harbor WA

1. Pioneer Way restaurants & sweet treats

Pioneer Way is Oak Harbor’s original Old Town, and is one block from the harbor.  There are some great restaurants in this district, including Rustica Italian RestaurantNoe Jose Café (Mexican), and Frasers Gourmet Hideway (upscale steak and seafood). 

Visitors with a sweet tooth will love the old style Popsies Candy Store, delicious SooBerry Good (dessert shop), and trendy Mad Batter Cookies (bakery and coffee shop).

Mad Batter Cookies is pictured above.

Whidbey Island Coffee is also along Pioneer Way, and has breakfast sandwiches, wraps, salads and beverages.

2. Pioneer Way shops

The Garry Oak Gallery is along Pioneer Way, and is an artist’s collective with both affordable and high-end works.  Purple Moon is next door, with a selection of quirky and unique gifts.

Cross the road to browse cottage style home goods at Little Town Cottage, right next to Pacific Northwest Vibes Market, that sells a wide variety of goods from local vendors, ranging from goat milk soap, to artisan jewelry.

3. THE LOFT on Fidalgo & Dock

The trendy LOFT on Fidalgo & Dock is one street back from Pioneer Way, and has a fun set of businesses inside the renovated Feed and Seed building (1937).

Stop by Hive Jive for honeycomb and honey tasting flights from local farms, and Whidbey Island Bagel Factory to indulge in 23 varieties of NY style bagels.

4. Windjammer Park

The 28.5-acre Windjammer Park sits on Oak Harbor’s waterfront, and is a popular recreational area. It has picnic areas, an amazing splash park, lagoon and playground.

The highlight is the Shipwreck Shores Splash Park water feature, with a pirate ship, lazy river and fountain feature. 

The lagoon is directly west of the Splash Park, with a popular beach, and dock from the 1950s (no lifeguards).

Cross the bridge over the lagoon at Windjammer Park.

Kids will also love Bailey’s Playground at Windjammer Park.

Look out for the "Story Trail" along the paved path at Windjammer Park, with excerpts from children's books for the whole family to read.

5. Oak Harbor Waterfront Trail (1-mile)

The Oak Harbor Waterfront Trail (1-mile) starts at Flintstone Park, and ends at the Scenic Heights Trailhead Park.  Leashed dogs are permitted on this trail. 

Along the way you will see the cool Flintstone car at Flintstone Park, then walk along a beachfront boardwalk past condos, before passing the Windjammer Park with playground, splash park and lagoon.  

The trail then crosses Beeksma Drive, before heading inland at Theodore Park along the Freund Marsh.  It then travels uphill to a spectacular overlook at the Scenic Heights Trailhead Park, with interpretive signs explaining Oak Harbor’s fascinating history. 

6. Fort Nugent Park

Fort Nugent Park is a 1.5 mile drive inland from Windjammer Park at Oak Harbor, and has a fabulous fortress-like playground that’s a big hit with kids.  There’s also an 18-disc golf course.

7. Roller Barn

The Roller Barn is a vintage roller skating rink in Oak Harbor, housed in the magnificent Neil Barn.  The Neil Barn was constructed in 1912, and converted to a roller skating rink in 1950.  It’s adjacent to an old water tower from the original 1894 farm.  Check hours at The Roller Barn.

8. Blue Fox Drive-in Theater

Take a step back in time to a retro drive-in theater at Oak Harbor.  The Blue Fox Drive-in Theater opened in 1959, and has first-run double feature movies that extend well after midnight. Don’t forget to bring lots of pillows and blankets to keep warm!

There’s also an arcade, seasonal go-cart track, tavern and beer garden and snack bar.  Overnight camping is even allowed!  This is a really affordable night out for a family.  Check hours.

9.  Pacific Northwest Naval Museum

The excellent Pacific Northwest Naval Museum has 4,700 square feet of exhibits, showcasing Oak Harbor’s transformation from a sleepy farming town settled back in 1850, to the creation of a major naval base in 1942 during WWII, fueled by fear of foreign attack.

Kids can play on two flight simulators for fighter jets at the museum, operate a nose gun turret, try on night vision goggles, and see a WWII-era Catalina aircraft. Check hours.

10.  North Whidbey Farm

Visit a working goat farm just north of Oak Harbor WA, where you can pet goats and baby goats, and purchase farm-made products like goat cheese, cheese and caramel sauces, soap and lotions.  The farm has been operational since 1935! Check hours.

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