2 Day Oak Harbor Itinerary

Oak Harbor Marina

Oak Harbor is a small city on a rural island—the best of all worlds! It’s a getaway from the super-sized metropolis, but with a wide variety of outdoors and cultural happenings that create a perfect vacation weekend!


Take Interstate 5 from Seattle or Vancouver B.C. to the SR. 20 Interchange and head west. Follow SR 20 around Sharpe’s Corner to Whidbey Island. When you’ve crossed the Deception Pass Bridge, you’ve got it made! While Deception Pass State Park is a great place to stop, resist the temptation, because we have you coming back at a better time.
After the drive, it’s time to stretch your legs with a stroll along Pioneer Way. Public art entertains the senses from one end of downtown to the other. The Gary Oak Gallery inside the Harborside Village is an artist’s collective where you’ll see new and beautiful things each time you visit. Inside the shops you’ll find more arts and crafts, decorative items, clothing and books. Be sure the check the special section of regional books.
One block south of downtown along the waterfront is Alfies Pizza. The restaurant offers view of the water and a casual atmosphere with vote-winning pizza and more.
Options – Riverside Cafe, Noe Jose
When the Navy built bases near Oak Harbor, the town grew quickly from a tiny town to a real city. The first reason the Navy came was they needed a place to supply their Catalina PBY aircraft – essentially flying boats that could land and take off on water. The PBY museum explores, not only those early PBY years, but Naval life on the island in general. There’s even a PBY aircraft to explore along with trainers where you can try your own hand at flying any of several aircraft.

Family Friendly Oak Harbor

Oak Harbor has lots of young families with children. So, visiting here with children is really easy and fun. Some of the activities are really old-school, which means mom and dad will want in on this as well! There’s a roller rink in a big ole’ barn in the middle of town! There’s an real-life drive in theatre that’s been upgraded to digital for the latest movies. Before showtime, the Blue Fox Drive-in also has go-karts! Just as important, there are lots of affordable restaurants where you can feed everyone and not spend a lot.

Historic Downtown Oak Harbor – home to many festivals and events.

Afternoon and Evening
You’re on an island and it’s time to find some beaches and other cool things! If it’s still around lunchtime and you don’t want to sit inside, grab your pizza to go, or hit one of the drive-thru restaurants in Oak Harbor and bring your lunch to a scenic park south of the city! Fort Casey State Park features a military fort built before World War I! Find out why it was part of the vaunted “triangle of fire” defense. Right next to the fort is Admiralty Head Lighthouse, with sweeping views of the water. There are plenty of spaces for a picnic.
Working your way back to Oak Harbor is Fort Ebey. Built for World War II, the park is better known for it’s beaches, bike trials, kite-flying, and cliffs for hang-gliding!
You’ve packed so much into just one day that you may be ready for dinner. But if you have time, relax with a drive along the west side of Whidbey Island. West beach has a spectacular pull out for watching the water while a county park at the end of Libby Road has great beach access for watching the sun set.
If you’ve had enough of the car, head back downtown for a relaxing glass of wine at Rustica or the Terrace Wine Bar and Bistro. Beer lovers will want to head uphill a block to the Whidbey Beer Works or up to Flyers.
It’s decision time for dinner with two Oak Harbor signature restaurants. Frasers, is just a block off Pioneer. Chef Scott Fraser and his French-trained culinary skills presents enchanting dinners that promote the bounty of the Northwest. At Seabolts, the Northwest is featured through seafood. From home-smoked salmon and chips to salads topped with grilled fish, it’s all about fish here. But, there are also delicious not fish entrees as well.
Options – China City, El Cazador Mexican Grill, Zorba’s Greek and Italian Restaurant

Oak Harbor – A Base for All Puget Sound

There’s so much to do around here that you could base a whole week’s visit from Oak Harbor. Take a ferry trip to Port Townsend for the day. Explore Coupeville and South Whidbey. Take a day trip to Camano Island and La Conner. Spend a day in Anacortes. Think of Oak Harbor as the center of spokes on a wheel, and you have the reason to spend an entire week!

Deception Pass Sunset

Play Outside
Morning Walk # 1 — Get a unique view of Oak Harbor. Head to the beautiful Oak Harbor Marina and follow the signs that point out the route to the Maylor Point walking trail. The trail follows a route on the far side of Crescent Harbor from the city. It’s a favorite walking or jogging trail for locals, but stay on the path. You’re actually on NAS Whidbey property!
Morning Walk #2 – The Oaks of Oak Harbor. This is part walk, part drive. Find the brochure for the Garry Oaks of Oak Harbor and follow it to find the magnificent trees that gave the city its name.
Riverside Cafe downtown is a locals favorite with a variety of breakfast options that will please everyone.
If you fish, then today is your day. You’re on an island in the middle of Puget Sound and there are plenty of great spots. You’ll need a fishing license, of course, but after that you can head to any of the state parks for a day of salt-water fishing along the shore. When the salmon are running there are plenty of great spots all along the north and west side of Whidbey Island. Deception Pass has two fresh water lakes for trout, bass, and perch. You should plan ahead to find the best fishing.
At low tide, you can also go clamming at any of several beaches on the island. You’ll need a license and need to plan ahead for the tides and places open for clamming.

If you don’t fish, or don’t have a way to get it home, then just play outside!
Let’s head south for the morning. Fort Casey and Admiralty Head Lighthouse offer spectacular views of Admiralty Inlet. There are trails to suit every hiker, experienced or not. The fort was one of three built in the 1890’s to defend Puget Sound from invasion. The Admiralty Head Lighthouse, first operated in 1861, was the first built on Puget Sound. Nearby is Fort Ebey, built as a result of World War II. The park features numerous hiking and biking trails. They run through a region known as the “kettles” dug-out patches in the earth left by retreating glaciers.
Also, stop at 3 Sisters Farm Store for quality locally-made goods. Even if you don’t have a way to buy and take home many of their products, it’s always fun to look!

Head to one of the places we’ve listed here that you missed, or try something else that you saw. If you walked before breakfast (or slept in) then breakfast might have really been brunch and you’re ready to go-see-do!
You could spend days at Deception Pass State Park. There are hiking trails, fresh water lakes, beaches, and that amazing bridge about 18 stores above the waters of Deception Pass. A favorite way to see the park is to get there early. The park opens at 8 a.m. Another plan would be to visit in the off-season. This rugged country is a fun visit for people looking to get the full feel of the Northwest in winter.
But, whatever you do, make sure you take the Deception Pass Jet Boat tour. The wide-open boat offers great opportunities for viewing the wildlife and sea life, and the trip through Deception Pass is amazing!

Necessary Shopping

If your Oak Harbor adventure is on a weekend you should have been running errands, you can sneak some of that in, too. Oak Harbor has major chain stores, hardware stores, supermarkets, and more.

See what we did here?

We gave you a two-day itinerary, but it would take you maybe five days or more to do it all! Oops, our bad. We hope you’ll come back soon and enjoy what you missed!