One of the best ways to see the USA is by packing up your rental car and heading out on an old school road trip.

One of the best ways to see the USA is by packing up your rental car and heading out on an old school road trip.

Foundry / Pixabay

The size of the country means that you could drive for days and not even get halfway across it, so be sure to pick a road trip that will include plenty of gay-friendly cities and towns so that you can make the most of your gay travels in the USA.

Not all road trips are created equal, and after spending a lot of time in the States, it’s easy to take for granted that the gays are everywhere. While most areas are fairly accepting of the LGBT community, there’s a significant black hole of gay life in small towns across America. So where’s a good place to take a gay road trip in the USA?

Starting in Chicago

Chicago is an ideal starting point for a great road trip of any kind, with plenty of flights everyday on airlines such as Virgin Atlantic and it’s partner Delta (like alliance partner, not life-partner), it’s an ideal starting/ending point. Chicago is one of America’s largest and most cosmopolitan cities, but unlike locations like New York, LA, and even San Francisco, Chicago is a much more manageable metropolis.

The entire downtown region can easily be explored on foot, so take the time to wander around from the world-famous Willis Tower (which used to be called the Sears Tower, and still is by most locals), to the riverfront that stretches throughout the city, to the lakefront beach.

Chicago architecture

Chicago is a city that’s known for its amazing architecture, and despite the looming presence of Trump tower, it’s easily one of the prettiest big cities I’ve ever visited in the States. Though there are numerous skyscrapers (definitely visit the SkyDeck in the Willis Tower, the views are breathtaking… if the weather is nice that is) the city layout means that you never feel towered over, with plenty of bright blue sky on show at all times (again, weather permitting).

350543 / Pixabay

Gay Chicago

Chicago is also SUPER gay-friendly with a few distinct gay neighborhoods you can explore to get your LGBT fix before you hit the road. Boystown delivers on its name, with a somewhat twink-orientated vibe, while nearby Andersonville better caters to those of us on the other side of 30. With loads of gay bars, gay cafés and gay restaurants to visit, the northern neighborhoods of Chicago are a vital part of any gay US getaway.

Route 66

Route 66 is one of America’s most famous road trip routes. Connecting Chicago with LA, travelling the full length of this iconic highway would take weeks, so we’d recommend exploring just a small portion of it on your road trip.

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ahundt / Pixabay

There are a number of Spingfields across America, and though you may not see any mention of the Simpsons here, Springfield Illinois is the state capital and home to the equally-important Abraham Lincoln. Abe was a long-rumoured homosexual (though nothing has ever been proven) and made a huge impact on the shape of the US as it is today, and the Abraham Lincoln Presidential Library and Museum is definitely worth a stop on your trip.

12019 / Pixabay

If you’re road tripping then be sure to make the most of it by stopping in one of the many cool and kitschy diners along the route. Route 66 Motorheads Bar, Grill & Museum is full of old cars, vintage road and neon signs, and a surprisingly good veggie-burger, making it a true slice of Americana that should not be missed. There’s also the Pink Elephant Antique Mall which sells – for the most part – a load of crap. But take the time to have a browse and you never know what you might find. I came away with some vintage comic books, 80s games, and a bag full of weird American candy as big as my head. Money well spent.

Alton (meet me in St Louis)

This small quaint town is just across the river from St Louis, making it a great spot to stop and explore. One of their best joints in the Old Bakery Beer Company where they brew their own craft beers and serve it with great organic food.

St Louis is a natural stopping point for many road tripping tourists who could then opt to fly out of the city, or backtrack their way along Route 66 to Chicago, which is a long drive but totally doable.

Another option would be to then follow the Great River Road upwards along the Mississippi to Minneapolis & Saint Paul… but that’s another story altogether.

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Tour Operator – Bon Voyage. Tel: 0800 316 1094.

The Great Lakes USA is the largest expanse of freshwater in the world with a unique and diverse landscape. This region, which is the size of continental Europe, includes the U.S. states of Illinois, Indiana, Michigan, Minnesota, Ohio, and Wisconsin. Go to for more information and suggested itineraries.

About the author: Nick Baker

Travel is such a huge part of modern life, and having grown up overseas and lived as a digital nomad no one gets that more than me.

As the world gets smaller we're constantly looking for new and exciting places to visit that are safe and welcoming to the LGBT+ community.