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A Living Bridge

Driving West Again After 25 Years in SF

Posted on February 25, 2026, by Peter Loomis



Introduction
1. Go West, Young Man
2. The Van
3. Decision
4. Preparation
5. On the Road
6. Back In the Bay
7. A Living Bridge
Conclusion

Introduction

After the holidays last year, I stayed back home in Milwaukee with my mom during January through her 85th birthday at the end of the month. She has been rehabilitating from a gastrointestinal infection and subsequent hospitalization last Fall. So, I went home in mid-December and stayed until early February.

While I was gone, my car in San Francisco became unusable, due to unforeseen circumstances. It was the holidays and the whole process of arranging to have it car towed and appraised, accepting the settlement, getting it salvaged and moving on emotionally took weeks.

Since I was there, I focused on preparing for Christmas, New Years and ultimately my Mom’s birthday at the end of January. I also helped with the house, clearing boxes, cardboard and paper recycling from the basement and garage. I brought old clothes to the Rescue Mission and several things to Goodwill. Donated several boxes of books to the local library.

Last time I was back, I got a battery tender for our second car which didn’t get used as often. It was my late father’s van. He died in 2023. Since then, my mom tried to drive it regularly and I drove it as much as possible on extended drives while I was back. This time the battery started to beep so I reattached the tender, plugging it in for a few nights of charge in the deepening cold December Wisconsin winter.

When I found out about my car being decommissioned in the Bay Area, it was Christmas eve eve. And it was confirmed — agonizingly and repeatedly — over the next several days while dealing with the insurance appraiser and adjuster, mechanics and eventually towing, re-titling and salvage services.

The holidays came and went. I didn’t have bandwidth to think about it. I figured I would handle everything when I got back. We had my brother, sister and uncle in town. A rare time with my mother living alongside her at home in Shorewood. Then her 85th birthday to plan and focus on.

It was only after my sister left for the second time since I had been there, the day after my Mom’s celebration, that I could — had to — finally start to think about going back to San Francisco. The next morning I looked at the van in our back carport, snow topping its roof and bumpers. Ready. Waiting.

Me as a young man standing by a yellow moving truck

After a few years living and working in New York City, I felt the call, packed my stuff and set out for San Francisco.

1. Go West, Young Man

Just as the dot com bubble was bursting in the year 2000, I decided to moving from from New York to San Francisco. For two plus years prior, I worked for an interactive agency called Interactiv8 that merged into a larger conglomerate named Luminant Worldwide. They had just opened a branch out West and a former creative director of mine from the M&M's account was leading the office. But, I had to quit first before I could get rehired out there. It was a formality, I thought. No big deal.

Me as a young man at my desk in a New York agency

Back in the day circa 1998-99, me at my desk in New York City at Interactiv8 where I worked as a designer and production developer on A&E Networks features and the M&M's Motorsports Channel (section) of their website.

Leaving NYC, I drove first to a cousin's house in Cleveland. After two days, I made it to Milwaukee where my father hopped aboard for the rest of the drive. He was always up for a good road trip and helped me navigate as we drove West. Back then my parents had friends along the way. First, in Council Bluffs and then Denver. We’d usually go South from there to visit family in New Mexico. But when my Dad moved me out, we went via Salt Lake City to Reno so he could get a night of blackjack at the casinos there before we got to San Francisco.

A map showing the route from New York to San Francisco

My first crosscountry route West led me from New York City to San Francisco by way of Milwaukee, where I picked up my Dad who drove with me the rest of the way.

We listened to books on tape about the Indians which brought the landscape to life and captivated our attention as we drove through Nebraska and Colorado. We listened and talked. In Salt Lake City, he picked a spot to eat because we had an Entertainment Coupon for it. Of course it was good. But mostly it was exciting to be on that drive with my Dad manning the tiller, showing me the way and helping me get situated.

Our light blue Honda Odyssey parked in the back carport with a bit of snow on the roof.

"The big car" was used for roadtrips, taking my Mom and Dad around the country as well as hauling their artwork to craft and art fairs.

2. The Van

Now, two days before my flight, I looked out the kitchen window at the van parked in back, wondering to myself if I was ready to fly back in 2 days and not have a car, which was the outcome I was facing. Mind you, I live up Twin Peaks in San Francisco, which is a set of big hills in the middle of a hilly city. I had been planning to figure it out when I got there, to use the insurance settlement to look for another car. But, how I would even get to that car to view it or even buy? Also, how was I going to navigate daily life in San Francisco? It was beyond me still.

Was I really planning to come back in April to drive it West in May? It might be a better weather corridor. Otherwise, when would I come back and how would I use it? My mom had offered it to me — was I just going to let it sit here unused and waiting?

Brown leather, waterproof Dunham boots on a chair in a bedroom

A strikingly handsome pair of new boots, to be sure. But how was I going to fit these in my luggage going back to San Francisco?

3. New Boots

I arrived in Milwaukee with two pairs of fairly worn sneakers. A pair of New Balance running shoes and a pair of Asics high tops. The New Balance shoes are still fairly intact, except the sole is starting to wear excessively and the heel cups are completely shredded. Also the fabric on the toes is a bit dingy and stained from camping in dust and dirt. The Asics have a section of the toe where the stitching has come undone and looks ripped open. They both have mesh or fabric toppings and neither is waterproof.

We happened to go by a Stan’s footwear store to drop off some old shoes for recycling and my Mom suggested we look for some replacement sneakers, sandals and boots. I saw a pair of size 14 Dunham boots on the rack. They looked similar to a pair of Rockports that I had before which just ripped and were decommissioned in SF before I left. They fit well, were leather and fully waterproof.

The frozen beach and pier at Big Bay Park

I've never seen it so frozen and hushed at Big Bay. The pier was completely encrusted and the even the water turned to icy cells slushing against the build up along the shoreline.

3. Decision

As I was thinking about it, the idea started to gain momentum. But, I needed fresh air. Space to think. So, I headed to nearby Big Bay for some perspective at our nearest lakeside access point.

Was I really going to wait months potentially to use this car and regain mobility? Or, was I willing to front-load a few days of transit and some funds for gas and lodging along the way? When I asked my brother, he said without hesitation, "Drive." He had done longer roadtrips before. He even suggested the idea of making more of a trip out of it since I was going. But I had already been away for 8+ weeks, for me it was about getting back to San Francisco.

A painting of a man carrying wood on his back through the forest as a young girl plays with flowers

Le Père Jacques (The Wood Gatherer), 1881 by Jules Bastien-Lepage was one of my Dad's favorites in the Milwaukee Art Museum.

LEGACY

Was I ready to become the new steward of my dad’s van, "The Big Car?" My previous vehicle was a gift from my parents that meant the world to me; losing it was crushing. Inheriting his last van felt like a heavy, but necessary, transition. Could any other car ever mean as much?

TIMING & PLANNING

I’m a planner by nature, and the math was daunting: a 4-day solo push across the country versus a flight home. I wasn’t sure I was ready for multiple 12-hour days in a row, but the options were clear. I could fly home and restart in SF without a car — stalling my momentum — or, I could front-load the transit and start the year with full mobility.

LOGISTICS

Transporting the van was an option, but driving it was more cost-effective. More importantly, it solved the Catch-22 of my situation: I couldn't easily shop for a replacement car in SF without having a car to get to the dealerships. By driving the van out, I eliminated mobility downtime and saved the insurance settlement for the road ahead.

WEATHER

Driving through the mountains in mid-winter was a big hesitation. So, I analyzed forecasts for every city on the route. Luckily, as the data showed a clear window of favorable weather, uncertainty shifted into a plan.

The route from Milwaukee to San Francisco

My four-day route to: (1) Des Moines, (2) Cheyenne, (3) Salt Lake City, and (4) the final stretch to San Francisco.

San Francisco or Bust

Having done the drive once before with my Dad, I had a blueprint. I would try to get to Omaha (or Council Bluffs) the first night. The second night, I picked Cheyenne — near Denver but on I-80 — which saved time and simplified logistics by taking the most direct route. When I went with my Dad, we stayed in Salt Lake City. For my last day, I could either stop near Reno — or, I could make it to San Francisco if I started early.

The sun setting through our front trees and over the houses across the street

At the earliest, sunsets in Shorewood came around 4:15 pm in late December and the nights were long, making sunlight that much sweeter. San Francisco is essentially "just over those houses," following the sun's trajectory West.

4. Preparation

Once I made up my mind, I had more energy to prepare. I could fit everything I had gotten during the trip, including some gifts and new boots. I'd even have space to take leftovers, cookies, boxes of sodas and drinks. But, I needed to remember that I'd have to take it all in when I arrived. Break-ins are real in San Francisco. I’ve had my windows smashed numerous times. Now, I’ll want to protect my "new" car. So, I can bring some extras — but not too much — so I can still fit into my apartment when I get home!

The van had not been cleaned regularly or thoroughly on the inside for several years. So, I brought our Shop Vac out to the car port, running it through all the nooks and crannies. It was awesome, having a strong vacuum and private carport right there, just outside the house. In SF, I normally park on the street, up several flights of stairs and around the corner from my apartment, so tending to the van in such an easy, accessible way felt great. So, I cleaned it well, preparing for my ownership as well as the journey. If it took a little longer to prepare, so be it. I wasn’t going to have this kind of opportunity for a while so I needed to make sure it was done right.

I had been intending to leave at my normal anticipated flight departure time which was around 9 am. However, with the vacuuming, packing and other stuff I wanted to do, it was 3 pm when I left.