The Beautiful Oakland Hills – Who Says You Can’t Go Home Again?

Skyline Boulevard, Oakland, California. Photo Credit: Accidental Travel Writer.

70 Days Across America

Oakland, California, is a diverse city of 433,031 people. While the city has dozens of neighborhoods, most locals divide it into Downtown Oakland, West Oakland, North Oakland, and East Oakland – which are collectively thought of as the Flatlands – and the Oakland Hills.

Why I’m Here …

So what am I doing in the Oakland Hills? Actually, I went there to visit a childhood buddy who was still living in the ‘hood.

In fact, I hadn’t been back to Oakland, California, in 15 years. To celebrate a milestone birthday, I decided give myself the trip of a lifetime – a 70-day trip across the United States.

Oakland was the fifth stop on the Northern California leg of my epic trip, which I was dubbing 70 Days Across America.

But it was also the most emotional stop on my trip. Because this is the town I was born in. And this was the town I grew up in.

My previous stops included San FranciscoLos Altos, Napa, and Concord. Future stops would include Pleasanton, Santa Cruz, Sacramento, Santa Rosa, and Berkeley. And then I would head out of state.

Teenage Stomping Grounds

The Oakland Hills were my stomping grounds in my teenage years.

My family moved there “from down the road” just as I was about to commence junior high school. Even though I only spent about 10 years of my life there,  the wooded district has always held a special place in my heart.

On my last sojourn home, I went for a long walk through the ‘hood I had spent much of my youth in. In fact, I had expected to be gone for about five minutes.

However, I was gone for more than three hours. Just like the good old days. Some things never change.

Actually, I was visiting a childhood buddy who had never left home. And I was only going to walk down the street to take a photo of the family home that I had vacated more than three decades earlier.

Joaquin Miller Heights

Leaving my friend’s house.

“I’ll be right back,” I said as I walked out the door I had passed through countless times in decades past.

In fact, I had always felt welcome in that house. It had always felt like my second home. And nothing seemed to have changed. I felt equally welcome there now.

A car was parked in the driveway. Was anybody home?
Trees and shrubs had all but blocked the view of the house from the street.
The foliage had changed, but the house looked pretty much the same.
Posing for a selfie at the front walk.
My bedroom window was visible through plants that had been planted after I left.

The walk from my friend’s house to the family abode took less than a minute. A car was parked in the driveway. Did that mean someone was home?

Should I ring the doorbell and introduce myself?

The house itself looked pretty much the same. While there had been a few improvements, the basic colour-scheme had not been changed.

What had changed was the garden. It had been totally re-landscaped. And from the front of the property, the house had nearly disappeared behind the foliage.

After taking a few pictures, I intended to return to my friend’s house. But I couldn’t resist the temptation to continue my journey just a little bit further to see if any other changes had taken place.

For example, was the next-door neighbour still living there – or one of her daughters? What about the people down the street?

Like a magnet, something kept pulling me a bit further.

Empty Lots and New Houses

The next stretch looked pretty much the same. There had been a creek – one of the many that crisscross Oakland – and it had probably prevented the land from being developed.

I decided to keep on walking “just a little bit further”.

A few of the houses looked the same. But most of them had been upgraded. And there were several new houses where there had formerly been empty lots.

Overall, it seemed a bit posher than when I had lived there. Except there were no more stables …

One of the most unique things about living in the Oakland Hills when I was growing up was the number of people that kept horses.

At some point, I decided, “You’ve come this far. You might as well continue to the end of the road.”

Changing Bus Routes


The walk to Joaquin Miller Road was about a quarter of a mile. And it took me about 10 to 15 minutes to reach the intersection.

This is where I caught AC Transit heading down the hill to the newly opened Montera Junior High School, now called Montera Middle School.

And three years later, I started catching AC Transit buses traveling in the opposite direction to the newly opened high school on a hill.

According to the sign at the bus stop, 10 new bus routes had been added since I vacated the Oakland Hills. Really?

Except for the buses running to and from Skyline High School, the twice hourly buses had usually been all but empty by the time they reached this part of town.

So whatever happened to the 15A, which was my link to civilization?

It traveled down Joaquin Miller Road, over the Warren Freeway, past the Mormon Temple, and down Lincoln Road to the Dimond district.

From there, it wound its way through Central Oakland, past Oakland High School (our arch-rivals), and past Highland Hospital to 14th and Broadway in Downtown Oakland.

That’s as far as I ever got. But I believe it skirted West Oakland, continuing up through North Oakland into Berkeley and other unexplored points north.

Joaquin Miller Park


I couldn’t come all this way and not walk across the street to Joaquin Miller Park, one of Oakland’s many hidden gems.

In fact, the park adjoins the very massive Reinhardt-Redwood Regional Park, which runs the length of the Oakland/Berkeley Hills.

I remember reading once that it was actually the largest “urban park” in the United States. Unfortunately, I was not able to verify that.

Poet of the Sierras

What I can verify is that the park was named after Joaquin Miller, the pen-name of Cincinnatus Hiner Miller (September 8, 1837 – February 17, 1913), a.k.a. the Poet of the Sierras.

While he was born in Indiana, Joaquin relocated to a massive estate in the Oakland Hills in 1886 – about 70 years before we did.

It seemed like such a long time when I was a teemager. But it doesn’t seem like such a long time now.

Anyway, Joaquin replanted the landscape – whose giant redwoods had fallen victim to the voracious demand for wood as the San Francisco Bay Area developed following the California Gold Rush of 1849 – with pines, cypress, acacia, and eucalyptus – a disastrous move.

For the latter all had to be chopped down following a prolonged cold snap in the early 1970s. And I remember it clearly!

For perhaps the only time in recorded history, the Oakland Hills were blanketed with a snowfall that remained on the ground for about two weeks.

And it was picture-postcard perfect!

Although the eucalyptus trees had survived for several decades, they could not survive sub-freezing temperatures for a protracted length of time.

As a result, they died, representing a serious fire hazard because their oil content is highly combustible.

Therefore, they all had to be chopped down, denuding the district for the second time. But this time to prevent forest fires rather than feed housing and commercial development …

The White Witch

Upon Joaquin’s death, the land was bequeathed to the city, hence the park.

But his daughter, Juanita, was allowed to remain. And she still occupied a house along Joaquin Miller Road when my family was still living at the foot of the hill.

According to the kids in the ‘hood, if you knocked on her door, she would open it and recite her father’s poetry.

It was sort of a dare. And nobody I knew had the nerve to find out if it were true.

In fact, she had quite a reputation. I  remember once seeing a black hot rod speeding up Joaquin Miller Road, with the words “Hell Cat” painted on the side. And that was pretty scandalous in the staid 1950s!

“There goes the White Witch,” one of the denizens of the neighborhood screamed. That was Juanita’s nickname.  In fact, she was a part of East Bay Lore.

There will be more on Joaquin Miller Park in a future blog post.

Upper Joaquin Miller Road


After exploring Joaquin Miller Park, I was tempted to walk back to my friend’s house. But I didn’t. Something kept urging me to continue.

So I turned left and continued up Joaquin Miller Road. After all, there was another route “home”. I could always return by way of Crestmont.

Skyline Boulevard

The dense forest slowly gave way to wide-open spaces as Joaquin Miller Road merged into Skyline Boulevard.

There were sweeping views of the rolling hills of  Contra Costa County to the left. And to the right, there were sweeping views of San Francisco Bay.

There were a few spectacular homes on one side of the road. And to other was Crestmont, a neighborhood of tract homes that were being built about the same time we moved into the family abode.

Crestmont offered an alternate route home. And I could have easily found my way back to my friend’s house if I had taken it.

But I didn’t. Instead, I kept walking forward, overcome by the ever-changing landscape that is so typical of Northern California.

As I was approaching Redwood Road, I was in for a surprise.

The very upscale Skyline Market, which was one of the last supermarkets in Oakland to have actual butchers, had been redeveloped into a retirement home called Sunrise Senior Living!

Should I go inside and inquire how much it would cost to live there? Like a falling leaf, should I return to my roots?

Crossing Redwood Road


I had come this far. So there was no turning back now. I might as well keep going.

As soon as I crossed Redwood Road, the landscape changed yet again. And the tall trees overhead again created long shadows. I remembered how this strip of Skyline Boulevard didn’t have street lamps.

Because of its high elevation, it was subject to thick spring and summer fogs. So tiny lights were embedded into the curbs, creating a sort of “runway” effect.

Sometimes, we would turn out the headlights when driving along this stretch of road late at night or early in the morning. And it was pure magic!

Skyline, All Hail to Thee!


When I left my friend’s house, it hadn’t been my intention. But I made it all the way to my alma mater, Skyline High School (Go Titans!),which was a pretty long walk.

On previous trips home, I was able to enter the campus unimpeded. That’s where I took art classes. The Foreign Language Building is over there. My English, typing, and math classes were in the portables at the back of the campus. Are they still there?

And that’s where the  cafeteria was, with that spectacular view of Mount Diablo in the distance.

Senior Lawn

Most emotional was always the Senior Lawn. Not that it held many memories of my high school days.  In fact, it hadn’t been my lunch-time hangout.

So why did it matter so much after I graduated?

You see, when I went to Skyline, it was a new school. We were the fourth graduating class. More importantly, we were the first class to spend our entire high school years at “the school on a hill”.

Oakland had been our universe, and Oakland’s five other public high schools had their time-honoured traditions, which had been passed down through the generations.

When my high school played my mother’s alma mater (she had also grown up in Oakland), she asked if they still did the same yells they did when she went there.

She was pleased when I told her after the game that, yes, they still did.

As students of a new school, it was up to us to establish our own traditions. And one of them was to embed the numbers of our graduating year on a pavement stone at the middle of the Senior Lawn.

Owing to our generosity of spirit, we (i.e., whoever was in charge of the class treasury) also paid for the previous three years’ graduating classes.

On my first few trips home, I was a bit stunned at how many years had been embedded into pavement stones since I had graduated. And on each trip home, the number of stones had increased.

House System

But times have changed. And on this trip home, the gates to the school had been chained shut.

Perhaps that was fate’s way of not reminding me how old I was – or of learning that some of the traditions we had so proudly introduced had been scrapped.

Not only had they changed the school colours. In addition, they had also done away with the house system, which we had been so proud of.

As we had been told, we were the only public high school in the United States to have a house system, which was actually a British tradition.

Did succeeding classes also stop embedding their graduating years on pavement stones? Could anyone still sing the school song?

And then there was the marvel of gazing at Mount Diablo in the distance. Surely, that will never change! Wasn’t this the most spectacular setting for a public high school on planet earth?

Football Games

In the early days, I was able to attend football games if my trip home coincided with football season. On one occasion, I was challenged at the gate when I attempted to buy a ticket.

Apparently, you couldn’t buy a ticket without a student body card from one of the two schools. Obviously, I had neither.

“Not just anyone can attend a game,” I was told by the gatekeeper.

When I looked crestfallen, the woman looked me in the eye and asked, “Are you the father of one of the players?”

I told the woman my name, and said, “Class of 66.”
“You don’t need a ticket,” she said. “Sit wherever you want.”

And in case you didn’t know it, Tom Hanks graduated from the same school I did, but several years later.

We had one more thing in common, Neither one of us was on the high school football team.

But at least I can say I went to the same high school as a world-famous movie star!

Home Sweet Home

What a magical place to grow up in! As I meandered through the beautiful Oakland Hills, I was truly awestruck by the beauty and grandeur of the majestic redwood trees and pine trees and other trees whose names I do not know.

But growing up amongst them, they had always seemed like nothing more than a quiet backdrop to our not-so-exciting Iives.

And I remember wondering frequently along the way, is it really true I once lived in such a beautiful place? Did I really actually grow up there? Why did I ever leave?

This lengthy blog post about my sojourn through the Oakland Hills was inspired by an article in Bay Nature magazine entitled Old Giants: The Last Days of Oakland’s Redwoods.

When I read this poetic essay, I learned things I didn’t know. And it touched something deep in my psyche, bringing back beautiful memories of my formative years.

As I have always said …

No matter how far I roam, there is no place like home!

Where to Stay 

For More Information 

You Might Also Enjoy 

This post on the Oakland Hills is part of a series chronicling my epic journey, 70 Days Across America.

12 Replies to “The Beautiful Oakland Hills – Who Says You Can’t Go Home Again?”

  1. Hi! So enjoyed your travel down memory lane! All was so familiar! Summer days we would pack a lunch and hike to the park… Cinderella Cabin, games of “kick the Can”, etc. Took dance lessons from Juanita Miller, watched Crestmont being built… one Easter vacation watching it slide down the hill. Skyline High… class of ‘63… on committee that wrote government constitution under the guidance of Mr. Trancina…have picture of fellow cheerleaders sitting on sign ( that was not red then). And, yes, after too many years, the words to the song are still there.., waving our banners, red and white! Thanks for the ride!!

    1. OMG! Thank you so much for sharing that with me! I cannot believe you actually took dance lessons from Juanita Miller! What was she like? BTW, were you really a cheerleader? I went to all of the football games and almost all of the basketball games. Would love to see that picture of you sitting on thesign in front of the school, if possible. I think it has been repainted numerous times through the years. It doesn’t look very “official”. I think people probably do it late at night – the way they did that rock near Monclare.

    2. Carol, I didn’t notice you name earlier. Actually, I think I know you. You were in my brother’s graduating class.

  2. Loved this trip back in time. I lived in Crestmont from 1958 until I was married in 1968, graduating from Skyline High in 1964. Walked every yard of your trip and much more in the incredible Oakland Hills. I live in Walnut Creek and drove through there all the time before the pandemic, coming home down the backside of Redwood Road. I’m ready to go back in time again.

    1. COOL! So glad you enjoyed this walk down Memory Lane! I also love driving along Radwood Road to Contra Costa County or Castro Valley.

  3. What a marvellous story about your time in Oakland! As we have talked about from time to time, I don’t think people have a clear understanding of the nuances of Oakland life.

    For me, I was struck by how green it all is and the fact that you have all these parks right outside your backdoor. I am sure there are many more adventures to share from a long gone era.

    What a real treat to be given a virtual tour by someone that has the old school knowledge of their neighbourhood. Kudos on a great story and I feel like I’ve walked up and down some of those streets with you 🙂

  4. Enjoyed your article, Michael. That is quite a walk uphill! I moved to Oakland in 1976 and it was interesting to read about the changes here.

Leave a Reply

%d bloggers like this: