Route 66, a National Treasure of the National Trust, winds its way some 2,400 miles from Chicago to Los Angeles. It weaves past small towns, big cities, national parks, roadside attractions, and also ... gay bars. As one of the first cross-country highways, Route 66 connected refugees from the Dust Bowl to safety in the 1930s, troops to military bases during World War II, and post-war Americans to California and the western states in the 1950s and onwards. While I traveled Route 66 with the National Trust from Chicago to Springfield, Missouri, I documented places in communities along the iconic highway that historically welcomed gay travelers.

The subject of gay bars from the past really interests me. Where I live in New York City I lead a walking tour about “gay bars that are gone” and people who attend share histories and sometimes memories from LGBTQ spaces, dating as far back as the 1870s. These are spaces where gay Americans found joy, love, community, and solidarity in the face of great social and political adversity. To document the “gay bars that are gone” of Route 66, I came with a few important things in my suitcase: two LGBTQ USA travel guides from the year 1966 (coincidentally) and a rainbow flag.

The travel guides were incredible. Both are rare finds and I had to convince folks from far away to scan archival copies and send to me. One was titled: "The Lavender Baedeker ‘66: A Guidebook to Gay, Interesting, Hysterical, and Historic Places in the U.S.," and it was published by a company listing LGBTQ-friendly establishments since 1961. The other guide was a Damron Guide from 1966, which is an LGBTQ travel company that still exists and has been publishing gay travel guides since 1964. This third edition Damron Guide chronicled more than 900 places across the United States and Canada recommended for gay travelers.

Aside from the dozens of gay bars serving Chicago, the first “gay bar that is gone” I came across was Esquire Cocktails in Joliet, Illinois, which existed in 1966 at 211 North Chicago Street and, according to the Damron Guide, served a mixed crowd while the “back part” was primarily for gay patrons. Fittingly, a lawyer’s office now exists where Esquire once did. I draped the rainbow flag over the door to mark the location and snapped a series of Polaroid pictures to document the site. Also noted in both guides is a bar called Trade Winds, with a Highway 66 address. The address proved too difficult to locate, but the fact that there was a gay bar scene in the relatively small city of Joliet (famous for its 1858 prison) amazed me.

Let’s remember what was happening in 1966 for gay Americans: in January 1966, Time magazine published a notorious article on “The Homosexual in America,” calling homosexuality “a pernicious sickness"; gay and transgender customers rioted at Compton’s Cafeteria protesting police harassment in San Francisco; and New Yorkers staged a “sip-in” protest at Julius bar in Greenwhich Village, protesting discriminatory practices by the New York State Liquor Authority. The Stonewall riots, credited with sparking the modern LGBT rights movement, were just a few years away.

In Springfield, Illinois—the “land of Lincoln”—I tracked down another mixed bar at 309 East Monroe Street named Two Brothers. It looked like a bar had operated there last, as the classic Anheuser Busch sign still swung above the entrance. Peering inside, it appeared to have been closed for some time. Armed with the rainbow flag, I adorned the front door and took another series of pictures. According to The Lavender Baedeker, there was another gay bar in Springfield called Gee I Tavern, specifically for gay men, at 212 N 5th St. That address is now Union Square Park. Interestingly, a gay bar called Smokey’s Den was not listed in either guide, but a local told me it was located right off of Route 66 in downtown Springfield.

St. Louis has long had a thriving gay scene and in 1966 (as best one can tell from these guides) counted 10 gay-friendly establishments including dive bars, clubs, coffee houses and hotels. One Fifteen Club (115 South 9th Street) stood in what seemed to be a former nightlife district where the new urban sculpture park, Citygarden, now presides. A sterile office high-rise now stands where One Fifteen once did.

St. Louis was my last stop for documenting “gay bars that are gone” along Route 66 before flying back to New York City out of Springfield, Missouri. It was a city where everyone seemed ready to have a conversation. One St. Louis resident told me about the one gay place he knew of in his hometown of Rolla, Missouri, some 100 miles west of St. Louis: the rest stop off of I-44 and Route 66. He told me, “Every gay man within miles called it Suzy’s. Like the name of a bar. You could say it in public, because straight people didn’t know the name. I-44 replaced 66, but the old road runs along 44 in that area.”