San Luis Obispo, California: Happiest City in America, Chewing on Everyone Else's Gum

Welcome to San Luis Obispo, California, the Central Coast town that locals call SLO, and that is also, coincidentally, how you'll be moving through it on a Thursday night. Sitting roughly halfway between San Francisco and Los Angeles, this college town of 47,063 people at the 2020 census has made a whole personality out of being pleasant. We love it. We're also going to poke it with a stick.

Bubblegum Alley and the Art of Public Saliva

Let's start with the town's most famous landmark, which is a wall of strangers' chewed gum. Bubblegum Alley runs about 70 feet off Higuera Street. It has been scraped clean before and grown right back, which makes it the only thing in SLO with more staying power than a Cal Poly grad living in their parents' guest house.

Visit California points visitors toward Higuera Street for boutique shopping, cafes, and the famous Bubblegum Alley, where kids can marvel (and maybe add to) the colorful walls. Yes, "maybe add to." Nothing says "family vacation" like handing a seven-year-old a wad of Bazooka and pointing at a wall.

If gum isn't your speed, SLO has a more upscale kind of excess: the Madonna Inn. It opened on Christmas Eve 1958 and today has 110 uniquely themed guest rooms and suites. The pink-drenched dining room is so committed to the bit that even the sugar on the tables is pink. Honestly, it's the most unhinged thing in a town that otherwise runs on oat milk and moderation.

Happiest City in America (Terms and Conditions Apply)

Oprah crowned SLO the happiest city in America back in 2006, and the town has been insufferable about it ever since. The catch is that housing here ranks among the least affordable in the country, so the happiness is mostly roommates and denial. Everyone's smiling because they're four deep in a two-bedroom and the Bishop Peak sunset is free.

And that sunset is a good one. The Bishop Peak Trail offers great views, which is convenient, because hiking a hill is the town's answer to every social question. What are you doing after work? Hiking a hill. Weekend plans? A different hill. First date? You get it.

In fairness, the county is at least trying to fix the housing mess. Whether that helps your rent before you're 40 remains to be seen.

Thursday Night Is a Religion, and Tri-Tip Is the Sacrament

SLO's social calendar is mostly one event. The Downtown Farmers' Market runs Thursday from 6:00 to 9:00 p.m. and spans about four blocks of downtown. With more than 120 vendors, it offers fresh produce, flowers, farm-to-table dinners for under $10, handmade goods and live entertainment. Translation: thousands of people shuffle past a smoking grill while a guy plays acoustic Sublime. Rain cancels it, which is the only time SLO has ever experienced genuine grief.

The sacrament is tri-tip, the Central Coast's beloved barbecue cut. Visitors can sample barbecued tri-tip while watching street performers and local bands. Firestone Grill locals treat its sandwich like a Michelin-starred miracle rather than beef on a buttered roll. Pro tip: it's delicious, and you'll have it again next Thursday.

Prefer your carbs in liquid form? The wineries of nearby Edna Valley are just 10 minutes from the town centre. Pierre Hyppolite Dallidet, an early winemaker in town, would be proud, or at least unsurprised.

From Tiger Town Bandits to Tech Bros in Patagonia Vests

SLO has real history, and the Spanish got here early. The Mission San Luis Obispo de Tolosa was the fifth in California's mission chain. Its roof was originally tule thatch, which flaming arrows set on fire, so it was covered in clay tiles instead. That is a very different approach to downtown security than "a guy on an e-bike yelled 'on your left.'"

The rough side of town was once called Barrio del Tigre, a lawless hotspot of brothels, gambling and saloons. Today the most dangerous criminals are tech workers riding e-bikes through crosswalks. We went from outlaws to guys in Patagonia vests, and the bandits had better taste in footwear.

The current drama is more civilized. The city is celebrating ARTober, with piano in the plaza throughout October. Piano in the plaza. Of course. Not a single stagecoach in sight.

The Verdict

San Luis Obispo, California is genuinely lovely, with its mission, its mountains, its pink hotel and its improbably good beef. It's also a town that has built a tourist attraction out of discarded gum and a social life out of one street closure. Come for the Central Coast charm, stay for the sunset, and bring a roommate.

Think we were too nice? See the full roast on RoastMyTown.com.