As a gay couple traveling the world, San Francisco and the Southwest of the United States were always high on our list. And while many associate the city with Golden Gate Bridge views and cable cars, we came for something far more meaningful for the LGBTQ+ community: the Castro Street Fair. This annual LGBTQ+ street festival in the United States of America, held in one of the most iconic queer neighborhoods in the world, was founded by none other than Harvey Milk in 1974. Arriving in early October, we joined thousands in celebrating queer visibility, creativity, and love right where LGBTQ+ history was made. This community-powered event should be on every LGBTQ+ travel itinerary. In this couple of men guide, we’ll share what makes the Castro Street Fair unique and dive into the life and legacy of Harvey Milk.
What is the Castro Street Fair?
Held annually on the first Sunday of October, the Castro Street Fair is a vibrant LGBTQ+ celebration in the heart of San Francisco. Unlike large-scale Pride parades, this event is rooted in community, creativity, and local culture. It stretches along Castro and 18th Streets, blending live music, art installations, drag performances, street food, and a marketplace of LGBTQ-owned businesses and nonprofits. No wonder that the Castro Street Fair got a spot in our 13 Top Highlights of our Road Trip South West USA!
What you can expect from the Castro Street Fair:
- Multiple live music and DJ stages
- Drag queen performances and dance floors
- Food trucks and craft beer stands
- Queer art, zines, and merchandise stalls
- Fundraising for local LGBTQ+ nonprofits
- A safe, inclusive, and celebratory atmosphere
Next Queer Event: 51st Castro Street Fair on October 5th, 2025!
Originally conceived to support the local queer economy, the fair has evolved into a joyful reminder of the Castro’s cultural roots. It attracts a diverse crowd: long-time residents, international visitors, allies, artists, and activists alike. And also we felt right at home!
Who was Harvey Milk – and why his legacy matters
Long before rainbow flags flew from every lamppost in the Castro, Harvey Milk helped shape this San Francisco neighborhood into a sanctuary for LGBTQ+ people. Harvey Milk, the first openly gay politician in California and a leader of the American Civil Rights Movement, was born on May 22, 1930, in Woodmere, New York. After moving to San Francisco’s Castro neighborhood, the heart of the city’s LGBTQ+ community, he co-founded the Castro Village Association to unite gay business owners and launched the inaugural Castro Street Fair in 1974. He believed in safe, strong neighborhoods supporting public education, affordable childcare, and equal rights for all.
In 1978, he was finally elected to the position of city supervisor in San Francisco, where he continued to advocate for equality for all people. In 2009, Harvey Milk Day was officially signed into law by then-Governor Arnold Schwarzenegger of California. And his work continues today through the work of the Milk Foundation, founded by his nephew, Stuart Milk, after Harvey Milk died. Interesting fact: Harvey Milk was included in a list of “The 100 Most Important People of the 20th Century” by Time magazine. We added him, of course, to our list of the most influential LGBTQ+ activists.
Key highlights of Harvey Milks life:
- First openly gay elected official in California (1978)
- Founder of the Castro Street Fair (1974)
- Advocate for LGBTQ+ rights, youth, and neighborhood unity
- Honored on Harvey Milk Day each May 22
- Named among Time Magazine’s 100 Most Influential People of the 20th Century
Milk became California’s first openly gay elected official in 1978. His political work focused on neighborhood empowerment, anti-discrimination policies, and public visibility. Tragically assassinated that same year, Milk’s legacy lives on through events like the Castro Street Fair and the global work of the Harvey Milk Foundation.
“The American Dream starts in the neighborhoods.”
— Harvey Milk
Promo Artwork for the LGBTQ+ Event in San Francisco
Our Experience at Castro Street Fair in San Francisco
San Francisco in late summer and early autumn is simply beautiful. We spent the late September days around San Francisco Bay, biking the Golden Gate Bridge, exploring Fisherman’s Warf, and enjoying some great restaurants in nearby Oakland and San Francisco. Part of our explorations of San Francisco has been the gay neighborhood of Castro, located right next to the well-known Mission District.
The first Weekend of October and our last days in San Francisco at the same time were dedicated to one of the best Gay Pride Festivals in California, the Castro Street Fair. Although the Folsom Street Fair and the San Francisco Pride are much more popular, the Castro Street Fair should not be forgotten on your Gay Pride Agenda. The area around Market Street junction, Castro Street, and 18th Street, with its Gay Bars, gay shops, gay-owned restaurants, and cafés, is simply the best part of the city for queer travelers. Here you can experience the real gay life in San Francisco.
After stepping off the subway at Castro Station, we were instantly greeted by a fabulous group of drag queens in full glam, offering tips on where to find the best drinks and shows. The streets were filled with rainbow flags, leather harnesses, glitter, and genuine joy. We felt like we had arrived home. Behind the iconic Castro Theatre, same-sex couples danced to Latin pop while others browsed handmade jewelry and queer zines. Street performers twirled batons, and volunteers distributed flyers promoting trans rights and HIV awareness. From young families with strollers to leather men in full gear, everyone was welcome. We danced on 18th Street, tasted local craft brews, chatted with LGBTQ+ elders about the fair’s early years, and ended the night with a drag show at Beaux that had us cheering until the final wig toss. This wasn’t just an event. It was a queer homecoming.
LGBTQ+ Nightlife in the Castro After the Fair
The Castro doesn’t sleep once the sun goes down. After the fair, the neighborhood transforms into a nightlife hub for queer San Franciscans and travelers alike. Various bars and clubs offer drinks and great parties all night long. We met a bunch of handsome men and joined them for some drinks at Q Bar and The Mix before having some of the best burgers in town at Hi Tops. Our highlight of our gay night out in the Castro District, San Francisco was the Drag Queen show performed by our beloved Alyssa Edwards at bar Beaux.
Our Nightlife Highlights in Castro, San Francisco:
- QBar – Classic Castro bar with strong drinks and pop music
- The Mix – Cozy, casual, and perfect for conversations
- Hi Tops – Gay sports bar with top-notch comfort food
- Beaux – Drag shows, themed nights, and a packed dance floor
Insider tip: Many bars host Castro Street Fair afterparties. We recommend asking locals or checking Instagram tags to find out where the crowds are heading. We hope we can attend another edition of the Castro Street Fair and become a part of the LGBTQ family of San Francisco again, at least for a weekend!
Some of our best pictures of the 2016 Castro Street Fair
It was fantastic! The moment we left the underground station at Market Street junction Castro Street, we were welcomed by a group of beautiful Drag Queens, answering our questions about where to go and what to do. And there we were, right in the middle of a colorful street festival. The mixed crowd of sexy gay guys, beers, teens, Drag Queens, and lesbians created such a lovely, friendly, and positive atmosphere. We felt at home on the other side of the world.
Reading tip: Understanding Queer Terminology with respect and Pride
Right behind The Castro Theater, a group of same-sex couples danced to Latino music, while Fair Stands offered beer and various gay and non-gay products on Castro Street and 18th Street. After crossing the junction, Castro Street and music stages on 18th Street with a dancing crowd made us and other visitors dance through the sunshine, take selfies, change numbers, and simply enjoy the great mood of everyone. All in all, Castro Street Fair is worth visiting while staying in San Francisco the first weekend in October. Proud. Free. LGBT. One Community.
Gay USA Travel Guide
Let’s get inspired by traveling to the country of boundless opportunities, the United States of America. We visited New York, Dutchess Country, California, the US-American Southwest, as well as Oregon, including Portland and Illinois, with stops in Chicago and Galena. And don’t forget to visit Disney Parks and Universal Studios!
More Articles for your gay travels to the USA:
- All about our stay at Sycamore Mineral Springs Resort >
- Our Review of the Yosemite Lakes Resort in a Yurt >
- All Articles of our 1-month Road Trip South West USA >
- Read our 13 Top Highlights Road Trip South West USA >
- Our gay-friendly Apartment The Willow in Los Angeles/ Hollywood >
- Enjoy all our photos, videos & stories of Gay Pride Trips Worldwide >
How to plan your visit to the Castro Street Fair
Thinking about attending? Planning ahead ensures a smooth and enjoyable experience at one of the most authentic LGBTQ+ events in the USA. Here are our top travel tips for experiencing the Castro Street Fair like a pro:
- When: First Sunday of October (e.g., October 5, 2025)
- Where: Castro & 18th Street, San Francisco, CA
- How to get there: Take MUNI Metro to Castro Station; expect street closures and high foot traffic.
- Admission: Free, with optional donations supporting LGBTQ+ nonprofits and community centers.
- What to wear: Express yourself! From rainbow gear to leather, drag, or casual jeans—anything goes. Be comfortable and weather-aware.
- Stay nearby: Look for LGBTQ+-friendly hotels or rentals in the Castro, Mission, or Lower Haight neighborhoods. Booking early is highly recommended as accommodations fill up fast during fair weekend.
- Food & drink: Many food stalls cater to diverse dietary needs (vegan, gluten-free, etc.). Bars often offer themed cocktails for the event.
- Accessibility: Streets are pedestrianized, and many areas are wheelchair accessible. Look out for info booths offering assistance.
- Safety and comfort: The event is primarily a queer family-friendly gathering during the day, transitioning to an adult-focused atmosphere in the evening. Always stay hydrated and wear sunscreen.
Support local LGBTQ+ Businesses in San Francisco
Support local LGBTQ+ businesses and learn about the history of LGBT activists firsthand. The experience of being among the queer community in San Francisco was refreshing and reminded us once again where we, as gay people, among all the other queer folks, come from. Nothing can be taken for granted, especially the right to be who you are. But of course, we had many more plans besides our lovely queer weekend in Castro.
Harvey Milk’s Castro Street Fair: Pride, Protest & Community
Biking the Golden Gate Bridge with sunset view, exploring the harbor area around Fisherman’s Warf, having drinks at Castro District, taking a walk at Golden Gate Park, or attending a Drag Show in one of the Theaters of San Francisco: The Castro Street Fair reminded us of the power of queer joy and grassroots activism. The queer community event is centered around rainbows, drag, and continuing a legacy that Harvey Milk helped establish. We left with full hearts, tired feet, and a renewed sense of belonging.
This event is an unforgettable way to experience the true spirit of the LGBTQ+ community, whether you’re a first-time visitor to San Francisco or a seasoned LGBTQ+ traveler to the USA. Our one-month road trip to the Southwest of the USA started and ended in San Francisco. It won’t be our last travel to S.F. and maybe even to the next Castro Street Fair.
For more travel news from and background on the LGBTQ+ community, follow Couple of Men on Instagram, Threads, YouTube, Pinterest, and Facebook!
Karl & Daan.
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