This April, I found myself in the Bay Area for work, staying in San Ramon for two nights. Not sure if you’ve ever been to San Ramon, but it’s safe to say there won’t be a blog post featuring it anytime soon. I thought I would be inundated with work tasks but found myself done by 2 p.m. I could either sit at the Hilton bar, which felt pretty lackluster, or find somewhere to go.

That’s how I stumbled upon Pleasanton, a place that was not on my California bucket list. Nevertheless, I grabbed my purse, a light jacket, and hailed an Uber.

Pleasanton is a 15-minute drive from San Ramon. I didn’t have an exact location in mind, so I had the driver drop me off in the center of town and started my solo afternoon.

Upon arrival, for a split second, I thought I had somehow gone back in time. Pleasanton looks like a well-preserved old California small town and a stark visual contrast to the almost sterile look of Bay Area communities modernized through the tech boom. It is walkable, leafy, quiet, and the type of place where kids ride bicycles with bells.

The historic downtown district is layered with late 19th-century wood-frame buildings alongside 20th-century stucco and low brick structures, with Victorian and bungalow-era homes lining the side streets. The Queen Anne influences such as bay windows, decorative trim, and porches add a whimsy, storybook charm, while the historic storefront facades provide an old-fashioned Western feel.

With no real destination, I walked along Main Street, reading plaques and signs about the town’s history. I learned from a painted mural that Pleasanton is home to one of the oldest one-mile horse racing tracks in the entire country, which shuttered in 2025.

I wandered into the local bookstore, Town Center Books, a small but well-stocked store with a friendly woman at the counter. I was impressed by their large selection of travel books and picked up a copy of Barcelona and Catalonia for my upcoming trip.

Afterward, I decided to check out Sabio on Main for happy hour, which I had noticed when my Uber first dropped me off. It’s an upscale bistro-style restaurant serving California cuisine using locally sourced ingredients. They had a great happy hour menu with $5 beers, $8 craft cocktails, and food items such as a cheese board—available in an individual portion too—wagyu meatballs, truffle grilled cheese, and my personal favorite, oysters.

I had a Paloma and six oysters, which came with a delicious and tangy green sauce. The gentleman behind the bar told me it was Sabio’s signature sauce made with lime, cilantro, and a few other ingredients. I struck up a conversation with a couple sitting nearby. Ironically, the husband was from Boston—this always seems to happen to me. They told me they come to Sabio for the wine selection, which changes frequently, and often visit another restaurant called Cellar Door.

It was too early for dinner, so I used Apple Maps to navigate myself to Cellar Door. I didn’t know it until I arrived, but I probably could have just followed the trail of people returning to Main Street with swirl cones because The Cellar sits directly next to Meadowlark Dairy, the busiest ice cream stand in town.

Rather than sit inside, I grabbed a table on the patio and ordered a gin cocktail called The Garden. It was refreshingly bright with grapefruit tonic and garnished with fresh slices of lemon, lime, grapefruit, cucumber, and peppercorns. It really was the whole garden.

As I relaxed on the patio looking out at the landscape, there was a feeling of sitting inside a Norman Rockwell painting. Between the old fire station, the grassy lawn outside the bandstand, and the constant stream of people walking by, everyone seemed to be heading to a high school pep rally or perpetually eating an ice cream cone.

I sat for a while, flipping through my new travel guide and couldn’t help but overhear bits of conversation from the teenagers heading to Meadowlark Dairy. Chatter of classmates, prom plans, and weekend activities floated through the air before I eventually made my way to dinner at Lokanta.

This was the standout spot of my entire afternoon.

Lokanta is a Mediterranean restaurant that sits in an eye catching, historic Main Street building with Western storefront influences, whitewashed brick facade and arched windows, giving the the aura that it has seen both the past and present of Pleasanton. Having enjoyed my earlier people-watching sessions, I opted to sit outside once again. The evening was getting cool, but the patio heaters kept things comfortable.

I ordered the highly recommended octopus and hummus. Both dishes were noteworthy, but the octopus remains at the forefront of my memories from this trip. It was a large grilled tentacle served with celery, garbanzo beans, parsley, and a lemon vinaigrette. The octopus was tender and flavorful with just the right amount of char around the edges and it struck a perfect balance between richness and freshness. The vinaigrette brightened the dish and complemented the smoky flavors.

I stayed for a little over an hour, watching people shuffle down the street: couples out for date night studying menus posted outside restaurants, families with kids still in baseball uniforms, and solo diners like me who may have also found themselves here unexpectedly.

As the evening slowly crept in and the lights on Main Street began to glow, I realized how grateful I was that my afternoon hadn’t gone according to plan. Had this work day been filled with more, well, work, I would have never wandered Pleasanton’s streets, learned about this unique town chatted with locals or discovered a new favorite octopus dish.

Pleasanton wasn’t a destination I sought out. It wasn’t on my itinerary, bucket list, or even on my radar. It was just the place I ended up when I chose curiosity over a hotel bar.