Arriving in Avalon.

• Trans-Catalina Trail from Avalon to Two Harbors
• Located on Catalina Island, this is a moderately challenging backpacking expedition. With a length of about 19 miles and an elevation gain of 4,700 feet, the trip took me three days.

• Distance from downtown San Diego: 65 miles to Dana Point Ferry
• Hike length: 19 miles • Difficulty: Strenuous • Season: October – May

It was my second night on Catalina Island and a pervasive chill was creeping up my hands and feet as a young moon rose in the night sky. Normally, I’d have been blissfully asleep, wrapped in my warm mummy sleeping bag. But not that night. For the second night in a row, I was lying in my single-person tent, trying not to shiver by clinging to my only source of warmth, a Mexican blanket I bought years ago in Tijuana.

I had made the decision not to bring my sleeping bag, because I wanted to field-test whether I could sleep comfortably with just a blanket. Why did I want to do this? Because I had to know whether I could cut a few ounces off my pack weight by swapping my sleeping bag with a blanket. Well, it turns out that not all ounces are equal; I should have brought a proper sleeping bag instead of the four-pound novel I carried with me.

Hiking the Trans Catalina Trail to Black Jack Campground.

I had spent the morning backpacking from Hermit’s Gulch to Black Jack. The distance was 9 miles with an ascent of 3115 feet, and I arrived at the second campground in the early afternoon. The next few hours were spent resting my achy feet, because not only did I forgo a sleeping bag, but I also decided not to bring my hiking boots. Instead, I brought my well-worn trail runners, causing me to spend the morning coming to terms with the fact that they weren’t designed to support both me and a 40-pound backpack for a multi-hour trek.

So far, the trip had been a bleary slog punctuated by a few pleasant moments, which included the ferry ride to Avalon, the coffee that I picked up there at daybreak, and the bison I saw just before stopping for lunch. Otherwise, I had spent the day tramping along endless hills and valleys of chaparral and green and brown grass. The thru-hikers that I met were a bit more reserved than the thru-hikers I was used to bumping into in the High Sierra, and I felt lonely as I passed them with just a wave and a “hello.” The rough-and-tumble series of events were beginning to hang over me. I was starting to wonder if I was getting too old to backpack and whether I should give it a rest. But then I reminded myself that I didn’t have enough money to travel any other way, and I rolled over in my tent and sighed. Sleep found me not long after.

Hiking to the air field from Black Jack.

I woke up the next morning as dawn’s rosy fingers cut through the low-lying fog that had crept uphill in the night from the coast. It took a half hour to break camp, pack my gear, and munch on a stale Cliff Bar. The air was still icy, so I started on the trail to warm myself. As I journeyed, I passed the island’s airport and stopped to take a photo of a shallow pond. I wasn’t able to secure a permit to camp at Little Harbor on the west side of the island, so I stepped off the Trans-Catalina Trail and stayed on the east side, where I found a battered trail that took me directly to Two Harbors. It was a 10-mile trek with an easier elevation change than the day before, only climbing around 1576 feet. Because I had fallen off the main path, I never saw a single soul, aside from a pair of silhouettes on a nearby peak.

Still hiking to the air field from Black Jack, but looking back.

Two Harbors was an absolute jewel. The campground was empty and quiet, though every once in a while I heard a playful squeal from someone on a jet ski in the water. There was a gentle breeze and the occasional squawk from a seagull. I stripped down to my hiking shorts and waded into the ocean. It was cold against my skin, but not cold like the penetrating chill from the previous night. As I bathed, I went over my itinerary in my head.

My camp at Two Harbors.

My initial plan had been to walk from Avalon to Two Harbors and then back to Avalon to take the ferry to Dana Point. But after two days of sore feet and two nights of poor sleep, I decided to cut short my experiment and take the ferry from Two Harbors to San Pedro the following morning. Once I got to San Pedro, I would still be about 50 miles from my car in Dana Point, so I’d have to improvise.

Sunset at Two Harbors.

As night fell, I warmed myself by a fire I built from leftover wood. Just above the flames, I could see the boats in the harbor swaying with the ocean current and I reflected on the fact that I was looking at the site where Natalie Wood died. At one point, an island fox emerged from the gloom and stepped into my camp – though it scampered off when I shifted in my chair to get a better look at it.

The next morning, I took the first ferry out of Two Harbors to San Pedro. I met a nice couple from Bakersfield who bought me a beer for the ride back. We spent the ferry ride chatting about our adventures. Once we docked, we went our separate ways. Everyone seemed to make a mad dash for their car — well, everyone except me. I chatted it up with a couple groups of backpackers and asked if they were headed south to San Diego, but they were headed north to L.A and wished me luck getting home.

Fortunately, my phone still had some juice and I walked along concrete and asphalt to the San Pedro Chamber of Commerce, where I bought a bus pass. My giant backpack attracted a lot of eyes from people on the street, except from the homeless. They nodded at me or left me alone. Eventually, I caught my bus and made it back to my car, four hours and three transfers later. The high point of the ride came when one of the bus drivers encouraged me to apply for a job because I looked down and out. He said they started at 18 dollars an hour, and for a moment, I considered the offer. I also enjoyed checking out the shops and mansions as the bus meandered through Laguna Beach.

Leaving Avalon to go to Hermit Gulch Campground.

Catalina is a charming island with a quaint coastal vibe. It can be desolate, but it can also be full of cheer if you look for company in the strangers backpacking alongside you. The richness of the island comes from its ability to let you experience remote conditions in a highly accessible area. This is good practice if you want to get a taste of backpacking without the risk that comes with being in a more inhospitable area. The modularity of the island’s trail system also allows you to carve the full 38.5 mile hike into smaller sections like I did; this is especially helpful if you want to experiment with your gear in the field. Simply put, Catalina Island is a sort of proving ground that can help you to develop a bit of character if you’ve forgotten, or have never known, the sharp taste of suffering and the gray face of defeat