Because Costco's Backyard Used to Be a Skydiving Strip

Why Issaquah? Because Costco's Backyard Used to Be a Skydiving Strip

Category: Local History (Bonus Post) | Suggested length: 700-800 words | Target reader: history-curious buyers and longtime residents

Here's a piece of local history most newcomers never hear.

From the early 1940s until 1987, a chunk of the Pickering family's dairy farm just north of what's now I-90 operated as a recreational airfield.

A Farm Turned Airfield

The field went through several names over the decades:

• The Seattle Sky Ranch

• Issaquah Airport

• Eventually, the Issaquah Skyport

It became genuinely woven into local identity. Weekly air shows, gliding, ballooning, and one of the region's best-known skydiving centers all operated from this one patch of farmland. Old Issaquah T-shirts showed parachutes floating over the valley, a small detail that tells you how central the Skyport was to how the town saw itself.

The Fight to Save It

The Skyport closed for good in 1987, after a long, emotional battle between residents who wanted to save it and developers who wanted to build on it.

The developers won.

THen and Now

Seven years later, in 1994, Costco moved its corporate headquarters onto land right next door.

Today, the nine-story Costco headquarters tower that's visible from the freeway sits almost exactly where skydivers once floated down onto a grass runway. It's a striking bit of then-and-now for a city whose skyline has changed more than most people realize, and a piece of history that rarely comes up unless someone who's been here long enough tells you about it.

For Buyers & Sellers

This kind of story is exactly what separates a generic relocation pitch from one that actually captures a place. It costs nothing to mention in a conversation with a buyer, and it tends to be the detail people remember.

Want more stories like this one? This is a bonus post in our Why Issaquah? series; the main series continues to cover the neighborhoods, outdoor life, and community that make the city worth choosing today. Reach out to Kelly Azzarello Real Estate any time.

Because South of Town, the City Limits Start to Disappear

Why Issaquah? Because South of Town, the City Limits Start to Disappear

Category: Neighborhood Deep Dive | Suggested length: 450-550 words | Target reader: buyers curious about the rural edge of the Issaquah identity | Companion piece to "Because Room to Roam Comes in Two Very Different Flavors," which covers the zoning and real estate specifics this post intentionally leaves out.

Head south past the last roundabout in the city and the character of the place changes fast.

Sidewalks give up and become shoulders. Lots stretch out. Streetlights get sparse, then stop. “Issaquah” starts meaning a school district and a mailing address more than a municipal government.

For buyers who want room without leaving the Issaquah identity behind entirely, this is the part of the map worth understanding, and where it actually starts.

Where the Sidewalks End

The transition isn't gradual. Within a few minutes' drive, you can go from a standard suburban block to genuinely rural roads, no streetlights, no sidewalks, lots measured in acres rather than square feet.

It's a different rhythm entirely: quieter roads, more distance between neighbors, the kind of quiet that doesn't exist anywhere inside the city line.

A Slower Pace, By Design

This isn't an accident of geography. It's zoning, built specifically to keep density low and lots large the farther out you go.

For the actual mechanics, real lot sizes, zoning categories, and the specific communities that anchor this side of the map, that's a companion post in this series: “Because Room to Roam Comes in Two Very Different Flavors.” This post is about the feel of it, not the parcel data.

Who Chooses This Side

Buyers drawn to this part of the map tend to want:

• Real acreage, room for animals, a shop, or just genuine distance from neighbors.
• An Issaquah School District address, without needing to be inside Issaquah's city limits.
• A trade-off they've already decided is worth it: well and septic instead of city utilities, a longer drive instead of a short one.

It's not the right fit for a buyer who wants sidewalks and a five-minute walk to a coffee shop. For a buyer who's already decided they want land, though, it's often the only part of the map that actually delivers it.

For Buyers & Sellers

Because this area still carries an Issaquah address, buyers researching “Issaquah” online often don't realize a specific listing sits outside city limits until well into their search. Flagging that distinction early, rather than letting a buyer discover it later, tends to build trust rather than cost it.

Curious how far south you'd need to go to get the space you're after? Reach out to Kelly Azzarello Real Estate and we'll map it out.

Because There's Always Something Happening Downtown

Why Issaquah? Because There's Always Something Happening Downtown

Category: Community & Events | Suggested length: 800-900 words | Target reader: buyers weighing community feel, families

Salmon Days gets the headline. It's really just the loudest night on a calendar that barely quiets down between May and September.

Here's the full rundown of what a summer actually looks like downtown, week by week.

Saturdays: The Farmers Market

The Issaquah Farmers Market runs Saturdays at the historic Pickering Barn, 9 a.m. to 2 p.m., May through September. It's a genuine destination market: more than 100 vendors on a typical weekend, live music, cooking demonstrations, and seasonal traditions like the Strawberry Festival and Kids' Day built right into the schedule.

Tuesdays and Thursdays: Free Music All Summer

Two separate weekly series keep the summer calendar busy:

• Concerts on the Green, Tuesday evenings on the Issaquah Community Center lawn, an eight-week season from early July through late August.
• Gas Station Blues, Thursday nights at the Historic Shell Station on Front Street, the same July-through-August stretch.

Both are free, family-friendly, and about as close to a standing weekly neighborhood tradition as a city this size gets.

August: The Whole Downtown Goes Car-Free

Al Fresco on Front closes Front Street to vehicle traffic every weekend in August, Saturday morning through Sunday night. Olde Town turns into a walkable, mall-like stretch of outdoor dining, sidewalk shopping, live music, and pop-up activities for four weekends straight.

A Few More Worth Knowing

• ArtWalk & Music Stroll, first Fridays through the summer, through historic downtown.
• Fenders on Front Street, a classic-car gathering that draws a crowd of its own.
• Ongoing Village Theatre productions, giving the city a genuine year-round arts anchor.

Then October: Salmon Days

Everything above builds toward the city's biggest weekend. Issaquah Salmon Days, held the first full weekend of October, is Washington's largest two-day festival: nearly 600 vendor booths, a Grande Parade, two live entertainment stages, and thousands of people watching salmon fight their way upstream past downtown. We cover it in its own post, since it deserves the space.

For Buyers & Sellers

For families weighing Issaquah against other Eastside cities, this calendar is often the tiebreaker. It's one thing to say a city has “community events.” It's another to show a buyer a weekly rhythm that runs from May through October without a real gap. Listings near downtown can lean into that specifically: walk to the market, walk to the concert, walk to the parade.

Want to know which Issaquah neighborhoods put you close enough to downtown to make this calendar part of your own routine? Reach out to Kelly Azzarello Real Estate.

Because Our Food Scene Is For Real

Let’s Start With Montalcino

Ask a local where to take someone for a special dinner in Issaquah and one name comes up before any other: Montalcino Ristorante Italiano.

Tucked into Olde Town on Alder Place, Montalcino is the kind of intimate, family-run Italian spot that makes you forget you're minutes from a freeway. It consistently ranks as the city's best-reviewed restaurant, known for handmade pasta, dry-aged meats, and a genuinely extensive wine list. It's the natural place to start any list of Issaquah's best restaurants.

Kelly, Pat and Sydney Azzarello along with Rick Regan (owner) and friend Delaney @ Montalcino

The Rest of the List

• Enzo's Bistro & Bar, on Gilman Boulevard, for elevated Italian in a similar register to Montalcino: house-made pasta, dry-aged meats, and a serious wine list of its own.

  • JaK's Grill, on Front Street North, the neighborhood steakhouse Issaquah has leaned on for two decades. Consistently rated among the Eastside's best for steak and service.

    • Paisley's Tea Room, a genuine afternoon-tea experience tucked between the Issaquah Alps and the Cascades, better for a celebratory lunch than a quick bite.

      • Capri Cellars, a Front Street bistro and Washington wine-tasting room, good for something lighter: a charcuterie board and a flight rather than a full dinner.

      • Honorable Mentions: Where to Grab a Drink

        Once you're downtown for dinner, the bar scene right around it is worth knowing too:

        • Vino Bella, a Front Street wine bar for something a little quieter.

          • The Rollin Log Tavern, a historic Sunset Way dive bar with real neighborhood roots.

            • Gaslamp Bar & Grill, a kid-friendly sports tavern with billiards and an easygoing, casual vibe.

            • A quick note: this list uses the confirmed business name, Gaslamp Bar & Grill, for the sports-tavern pick, since that's what turned up in research; if you had a different specific spot in mind, let us know and we'll swap it in.

              For Buyers & Sellers

              Issaquah isn't trying to be a nightlife destination, and that's fine. What it has is a genuinely solid, walkable restaurant cluster downtown, exactly the kind of thing that shows up in a buyer's “what's it like to actually live here” research. Listings within walking distance of Front Street can lean into that directly.

              Want a proper tour, dinner included? Reach out to Kelly Azzarello Real Estate and we'll show you around.