But decidedly worth the shout out to @josetexter. Keep the tips coming to @benjilanyado for tomorrow's time in Louisville and the road south!

And speaking of adventurers with a penchant for shaken cocktails, Benji's following in the footsteps of a somewhat famous fictional agent for MI6. 

Goldfinger might be remembered as the one with Oddjob, a character named Pussy Galore, and that extraordinary tagline – "Everything he touches turns to excitement!" – but it also features Kentucky, and in particular Fort Knox, just south of Louisville. 

The James Bond Wiki provides us this fantastic, convoluted summary of 007's sojourn into America's exotic heartland of darkness:

[After] flying to Kentucky … Bond sees the plan of Goldfinger to attack Fort Knox, tries to drop a note off to the CIA by putting it in the pocket of one of the mob members who was going to help Goldfinger, although he ended up being shot by Oddjob and crushed when his car was crushed into a cube. … Bond manages to convince Pussy Galore to change the nerve gas canisters in the planes about to attack Fort Knox with dummies, so that it has no effect on the soldiers there.

Then what? Bond is handcuffed, lowered into the vault, and forced to contend with lethal projectile hat. (Again, Kentucky and the hats?)

The Slugger is, first and foremost, a baseball bat, and arguably the best baseball bat. The Louisville factory has been making these bats for over 100 years, and according to their site, over 60% of pros use them when they step to the plate. In short, it's about as pure a symbol of Americana as you'll come across.

But the Louisville Slugger also happens to be 1oz bourbon, 2tsp blackberry brandy, 1oz dry vermouth, and lemons, shaken with ice. In other words, the Slugger's also quickly becoming symbol of Benji's night so far.

Lori has driven us to The Highlands, an artsy three and a half mile stretch 5 minutes from Louisville Downtown. It's famed for its contrasts: tattoo parlours side by side with white tablecloth restaurants.

Another case in point: Hunter S Thomson grew up here, but its most famous current resident is Mitch MConnell, the most powerful Republican in the country. 

The neighbourhood spread grew up around the vast Victorioan mansions on Cherokee Road – in the Great Gatsby, Cherokee Road was where Daisy was born and raised.

Things have changed, I'm in the back of @lori_mattingly's car, Gary up front in driver solidarity. @eaterlouisville has hijacked our food choice, and we're aimed for the Holy Grale, a converted Unitarian church in the Highlands – and which happened to be one of our expert picks before the trip got underway.

It's getting dark. We're still at the Garage. Manny, bless him, insisted on buying me and Gary some bourbon, despite the fact that he whooped my ass on the ping pong table. Southern hospitality at its finest.

Zach from @eaterlouisville has summoned some local royalty: Damaris Philips (@ChefDPhillips), who recently won the national Food Network Star competition.

A local star. We've been in this city for three hours, and already I have a very good feeling about it. We've forgotten to eat. We need to do something about that … 

Below the line, we've been told of an oddity on the route between Bloomington and Louisville; we unfortunately couldn't make it, but it's still worth a shout to both adamsjo2 and LiterateIndy for suggesting this bizarre "Eighth Wonder of the World", which happens to be part of the French Lick Resort. Really.

The West Baden Springs Hotel is worth a click here to check out it's strange and stunning architecture. The hotel as a whole encompasses stables, golf courses, a spa, and a 'natatorium' (read: extravagant indoor swimming pool). Wiki only provides a partial glimpse of its atrium:

The original spa was first built near local mineral springs over a hundred years ago, Jesuit priests once bought it for a dollar, and finally someone got round to declaring it a national historic landmark. 

[Editor's note: from all the arched eyebrows turned toward Benji, he must've just told them about the wind, his contacts, that bad grip on the paddle...]

Some of Hollis' friends have joined us here, along with Zach of @EaterLouisville, the local branch of the hugely popular national food blog Eater, which opened here last November – a sign of the times.

Very small, unimportant, not at all worth mentioning ever again side note: @MannyMassages beat me at table tennis, but it was really windy.

This place is excellent. An old garage with a fully gravelled front, dotted with benches, and the crucial table tennis tables, nets held together with wing mirrors.

Inside, there's a world of bourbon behind the bar on wooden shelves. Opposite, a tiled Neopolitan oven churning out pizzas. We're in 'NuLu' a rapidly rising strip full of bars and restaurants in the northeast of the city.

Indiana now belongs to London!

Though all eyes are rightly drawn to the epic matchup of Kentucky v London ping pong at Garage Bar, Louisville, is, in fact somewhat known for a certain annual equestrian competition.

Nothing is quite so ingrained into Louisville's DNA as the first race of the Triple Crown, the Kentucky Derby. Every year, the Downs are overrun by … everyone. At this point, the Derby is as famous for its horses (and gambling) as for its song, its mint juleps and its hats – its really strange hats.

A horse hasn't won all three races of the Crown since 1978, but in 2009, Mine That Bird came close, winning two of three spectacular fashion.

We've reached the Garage Bar. @MannyMassages is here and waiting. Serious game face. I send Gary in to battle. Manny calls me out. I smile like a Bond Villain. 

Boris is evidently on Benji's side.

Followed by delays, and then some more really intimidating smack talk.

God bless AirBnB. @ochaney tweeted that Louisville had some excellent listings, so we booked one from the car a few hours ago.

We meet Melvin, the flat owner, outside a grand downtown building and he takes us to the top floor, down a few corridors, to his beautiful loft (pic attached). It's superb … and had a SPIRAL STAIRCASE. It cost us £52 ($80.75).

He and a few others also left a few tips, one of which is for Garage Bar, our pre-ordained next destination. 

There, we have business to attend to: @MannyMassages has challenged us to a ping pong match. The winner buys a round of bourbon. 

Manny, I've got a surprise for you. I've got a guy. Gary, our driver, grew up with a ping pong table in his back garden. He's been mentally preparing since we crossed state lines into Kentucky. Hell, he's has been mentally preparing for this since childhood.

He's currently primed for battle, zen-like, repeating old Chinese mantras in a trance.

We'll see you in 10, Manny. 

He tweeted, brandishing an ear of corn … @MannyMassages, this is you're up against.

After serving up dinner plans to the crew, @MannyMassages challenges Benji to serve back.

Pretty serious: 95% of the world's supply comes from Kentucky. The sipping tips have already begun in earnest and the guys haven't even crossed state lines.

In fact, the major whiskey makers and a number of craft distilleries have banded together to organize the Kentucky Bourbon Trail, which ranges from Louisville and Lexington. 

The gang includes Jim Beam, Evan Williams, Wild Turkey and, of course, the recommended stop at Maker's Mark.

And you're feeling a bit bourbon-ed out after a full day, @GoWanderLou tells us of the Urban Bourban trail, and the Guardian's Erin Keane found the top 10 bars in Louisville. Some highlights:

Jack's Lounge: Bar manager Joy "Bad Girl of Bourbon" Perrine literally wrote the book on bourbon cocktails (The Kentucky Bourbon Cocktail Book), and her influence is evident in the bar's unfussy yet intelligent approach to Kentucky's native spirit.

The Holy Grale Inside: In this renovated church in the thick of the hopping Highlands, the city's beer geeks gather for evening services.

Don't let the Jazz Age opulence of this upscale downtown newcomer fool you – St Charles Exchange doesn't take itself too seriously. The inventive craft cocktail list includes locally sourced and house-made ingredients and changes frequently

Finally, a bit of literary tippage regarding a man who loved his mint juleps.

Benji's taken to the forum to plan tonight's victuals. Answers have come tumbling in, and so have more questions: what can be found at Hillbilly Tea? What are Kentucky Hot Browns? Will Holy Grale force Benji to pass a series of tests just to get a drink?

Nobody much knows what 'Hoosier' means, beyond "a resident of the state of Indiana". Etymology-wise, the only clue is that it might have been "used of anything unusually large".

So how about we just let Gene Hackman inspire everybody and go with his definition: winners.

Someone just alerted campus police … to complain about sartorial malfeasances.

Benji's just learned of a film called Breaking Away, which stars Bloomington and won an Oscar in 1979. The trailer shows us the story of a midwesterner with big dreams, trouble with quarry culture, and some pretty corny dialogue – "Smart move, shorty". A quick YouTube scan, however, reveals a slightly more thrilling clip inspired by a scene from the movie:

Benji's off to Kentucky, whose famous spirit was named for its history in Bourbon County, which in turn was named after the French House of Bourbon, a title that these days would make most Americans think of some mythical stash of barrels in a very large house.

Bourbon 101: Distilled from fermented corn, mostly, rather than the malted barley of scotch and the (more loosely defined) cereal grain of American whiskey. Wiki tells us that nobody knows who first distilled bourbon, but that a minister named Elijah Craig – who also gets credited with many Kentucky firsts, eg, fulling mill, paper mill, ropewalk, etc" – often gets the hat tip.

Where should Benji and the guys head to on the way to Louisville? And what should that lucky, non-designated driver have to drink?

We're Kentucky bound.

Matt walks us around the beautiful Indiana University campus, lined with imposing faculty buildings built with the trademark local limestone – cut from nearby quarries, the same stone was used to build the Empire State Building.

One of the faculties has a huge elm tree jutting through the middle of it – the family who sold the land to the university insisted that the tree could never be moved. Another was built with the proceeds of a Colgate patent purchase – it was a IU professor who invented fluoride.

Matt tells me about the university social scene. It's split between frat house preppy types, and a lefty hippie crowd. He sees himself as somewhere in the middle, leaning towards the latter.

He takes me into his statistics class, where I find a seat at the back. Appropriately, they're covering Central Tendency.

After Bloomington, where do Benji and the team head next, dear readers? May be, looking for bourbon now that they've lined their stomachs. Any recommends on the way to Louisville?

And Matt (@ces_matte) has come to join us for lunch!

He's a college senior and has skipped a statistics class to show us around campus. Don't tell his mum.

We've made it to Bloomington, the Indiana University town, and drive through campus to the tree-lined, lazy centre, where students are walking down broad alleys between wood slat houses. It feels like a seaside town in the middle of Indiana, with little shops selling luminous vests and tiny shorts emblazoned with the Hoosiers insignia - the college football team. We're set up on the front porch of the Runcible Spoon (recommended by @ces_matte), where every waitress is mild-mannered and tattooed.

In Bloomington, Indiana University student @ces_matte has been plying Benji with tips on Twitter. By way of thanks, we award him an honorary Guardian degree cum laude and give him the afternoon off classes.

A visit to TC Steele's converted farm up on a forest ridge in the Brown County State Park. In 1907 Steele turned seven abandoned farmhouses and fields of struggling sorghum and tobacco into his beautiful artistic refuge, spending day after day perched on the hills painting what he saw below him.

His wife designed four of the five trails that lace the 211-acre site, and we head down the "Trail of Silences" in between the oaks and hickory accompanied by a chorus of crickets.

Neatly, Steele ended his career as the artist-in-residence at Indiana University in Bloomington, our next stop.

Benji and the team are at the impressionist painter TC Steele's house near Belmont in Brown County. Here's what we've discovered about the most important of Indiana's Hoosier Group painters, famed for his Indiana landscapes:

As Steele explored new places to paint, he discovered an isolated area of Brown County, Indiana, where he built a hilltop studio-home... In August 1907 Steele married Selma Nuebacher, his daughter’s sister-in-law...

Whoa, back up, there - "he married his daughter's sister-in-law". Artists, eh?

...and brought her to their new summer home in Brown County. Inspired by the breezes blowing through the cottage’s screened porches, they named it the House of the Singing Winds. The land, while not suitable for agricultural purpose, provided Steele with "beautiful picturesque woods and hills and valleys."

According to the Indiana historical Society: "At first, his farmer neighbors thought Steele and his wife were strange. The Steeles were refined 'city folk' who did not seem to understand that the land was to be worked for profit, not captured in art."

Not to mention - he married his daughter's sister-in-law!

"Over time, the neighbors came to respect the artist."

Love this drive ...

Our straight-line route has warped into the forest, wild woods either side of us, the occasional beautiful log cabin.

We peel off following a crooked sign towards "Crooked Creek", over a rusty bridge with felled trees in the water either side.

Through tree tunnels and into the forests of the Brown County State Park, aiming for the house of impressionist painter TC Steele, deep in the woods - as recommended by @LiterateIndy.

We pass the huge Cummins Engine plant on the south side of town, and turn back through the residential outskirts, lined with two-storey Victorian white clapboard houses with yellowy-green dry lawns, flaking white air conditioning units propping up windows, topless grandpas sitting on porches. Crossroads America.

Back through the centre of town, past the Art Deco Central Fire Station, out onto the 46 West and the road to college town Bloomington.

We're on the outskirts of Columbus, an architectural outpost dubbed the Athens of the Prairie which was funded by industrialist and philanthropist J Irwin Miller in the 50s (the town was recommended by @stephani and @LiterateIndy).

Columbus, Indiana is worth a stop on your way from Indianapolis to Louisville. The city has a surprising collection of noteworthy buildings designed by noted architects like Eero Saarinen, I.M. Pei, among others. I enjoyed my afternoon there.

A quick coffee pitstop, and cultural comparison. Me - a middle class north Londoner - I go for a small caramel frappé. Hollis, our photographer from Nashville, who last night revealed he used to be a salmon boat captain in Alaska - he goes for an eight-shot monster, with chocolate sauce and a floater of milk on top. The coffee machine was churning out his drink for over two minutes.

On Twitter, @LiterateIndy (another regular tipster) has suggested a pit-stop at the home of late 19th/early 20th-century impressionist painter TC Steele between Columbus and Bloomington.

@woyce - who has been doing us proud with tips all week - has set a challenge: how many different ways are there to pronounce Louisville?

We've decided to take a deviation. Again. @ces_matte told us yesterday that there's a considerably more scenic route from Indy to Louisville, via Columbus, the university town of Bloomington, and Brown County state park. We're headed that way. Tips welcome.

@MAOneby's suggesting the Empire Quarry - just north of Bedford, where the stone for the Empire State Building comes from - for a swim. Hmmm.

Corn update: this end of the state, it's good and ready, dry and yellowing, scorched by a long hot summer - the less green the leaves, the closer they are to harvest.

Mellencamp - pah!

The Louisville Eccentric Observer can trump that. Here's their playlist for Kentucky. Hardcore, alt-country, jazz - and Bonnie "Prince" Billy. Pah-dum!

Send us your requests, and we'll play 'em: @benjilanyado, #TwiTrips, @GuardianTravel, or in the comments below

We're firmly anchored with corned beef hash, salami and eggs on rye, lox and bagels, and a third of a matzo ball each, and we're back on the I65 just beyond the Indianapolis city limits.

We've worked out a way of listening to the playlist you've been putting together for us via my Spotify account, Hollis's phone and a $10 service station aux cable. Currently: Jack & Diane by John Mellencamp. YEAHHHH LIFE GOES OOOOAAAAN.