Haight Street Afternoon


I see more of a local crowd on Haight Street than tourists and wonder how someone traveling to SF could not want to check out this neighborhood. OK, OK, there’s lots to do and see in the city. But even though I grew up going here to buy press-on tattoos of devils on Friday afternoons during my high school years and to study at cafés or sift through secondhand clothes in my early twenties, I still find myself wanting to check it out when in San Francisco. Of course, it’s changed since I left 12 years ago but for the better.

The Haight-Ashbury district of San Francisco, known to locals as simply The Haight, is legendary. In the 60s and 70s, the neighborhood, once populated by hippies, was known for its free love, hard drugs, and killer music. Even though you can still find good vibes, strong beer, and a HUGE selection of music at Amoeba, all things evolve. Now, it’s another lively San Francisco street but with a fair share of bohemian cool. Visitors will find a row of mostly high-end vintage boutiques, solid eateries or pubs, and specialty stores, with the token tie-dye and smoke shops, that together offer much beyond its hippie, homeless, or drug addict reputation. This is perhaps what keeps it, in my opinion, more of a local’s neighborhood than a tourist attraction—and the kind of urban street I love hunting down in new cities when traveling.

When I recently returned with my husband and daughter, we made a 3-stop hop aimed to appease each of us in a single afternoon.

1. For Him: La Rosa

La Rosa Vintage Boutique

dressThis is where my husband gets his suits when coming through San Francisco. La Rosa has remarkable vintage finds. From men’s fancy pajama sets to ladies’ ornate brooches, items for a special occasion are easy to spot here. But if you’ve been in or to the city enough, you know that San Franciscans use fancy vintage daily; why wait for a reason or than life, right? This shop is where my husband took 3 hours to pick out his wedding suit. I got tired of waiting so started snooping around and found a light caramel color English lace overlay on a peach slip dress to get married in. Beware if you walk in to browse; the chances of discovering something perfect are good, and it can put a slight dent in your wallet. Unlike some secondhand shops, everything is clean, neatly arranged and steamed. The racks are full yet not overflowing, and goods hail mostly from the 1920s to 1960s. It seems men where shorter and women had smaller frames, so sizes are a hit or miss. But that’s what alterations are for. I leave it to those crafty with a needle and thread to make it just right.


My favorite part of the boutique (ok, besides the hats) is the old luggage. I’ve seen a number of collectors’ vintage suitcases throughout my random visits.

pink lugguagetan luggage






Hats and luggage—yeah, I’ve got a thing for them. Must have been the early Mary Poppins exposure. Add books to the shortlist, of course. Apropos…

2. For Me: Booksmith


If there’s a bookstore in the area, I have to stop in. This quintessential neighborhood figure hosts tomes fresh off the press by local authors to best-sellers to philosophers from then and now. The revamped steampunk façade blends in with the Victorian architecture of the Painted Ladies in The Haight. The Booksmith’s window displays are more interesting than Macy’s during the holidays and usually contain a carefully curated bunch of books. I love their playful chalkboard art above their shelves. When in town and looking for where the local bibliophiles hang, I check out Booksmith’s Bookish Events listings for author readings and get-togethers.

window displaywindow also












During my last visit there, I discovered Out of Print, a new outfit that prints classic book cover designs on t-shirts, mainly, and uses part of the proceeds to donate books all over the world: “Books on shirts. Shirts on a mission. For each literary product sold, we donate one book to a community in need.” Bringing books to places that would otherwise not have access to them is honorable action through a fashion-forward mission—nice.

baby tees

3. For our 4-year-old: Ben and Jerry’s


Because she somewhat patiently endured all the browsing we did at the above two stops, we promised her ice cream. Yes, we bribe when desperate. We headed for “Peace, Love & Ice Cream” at Ben & Jerry’s on the iconic corner of Haight and Ashbury streets. The redhead behind the counter had a grin that would not let up. He continued smiling while we negotiated with our child over the size of her cone. He kept smiling after she deliberated over the chocolate flavor. And he was still smiling as we handed him a five. One scoop of mint chocolate chip in slow motion later, we headed back to the car about to expire its 2-hour parking limit.


*Update: La Rosa Vintage Boutique has since closed its doors, but there’s still Held Over, its sister second-hand shop down the street.

Go: There’s a lot more to do and see in The Haight. Hobson’s Choice is a good bar to start at with Happy Hour from 5-7pm. The vintage shops abound; go crazy. On Sundays, check out Hippie Hill on the west end of the street in Golden Gate Park. On that expanse of lawn, you’ll find every San Francisco type in one space. Jump into a dance or hacky sack circle, toss down a picnic blanket, or find a game of Ultimate Frisbee.

Read: Slouching Towards Bethlehem by Joan Didion. She gives in insider’s view of Haight Street kids in its heyday in a poignant personal essay in this collection.

Eat: From good Thai food to tapas, pitchers of sangria to craft beer, you’ll find it on Haight Street.

About Sam at Reading the Road

Hello, I'm Samantha, author and editor of READINGTHEROAD.COM, a blog journal of travelogues, travel stories, personal essays, articles, reflections, reviews, and poems in which travel and literature intersect.

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