The Bourbon Trail

Our national identity is to be found in diners and city parks, cypress swamps and little towns, local church services, at Home Depot, on city streets and lonely country roads.

I may have the wrong footwear for Buffalo…
As much as I like overseas travel, Iā€™ve never felt the urge to teach in another country. Landscape painting conveys a deeper shade of intimacy that I simply donā€™t feel when visiting other places. I enjoy them, but I donā€™t love them in the same way as I love the US and Canada.
I took this trip to pave the way for a workshop in the Deep South. Why didnā€™t I just head to the more familiar eastern seaboard states? Iā€™m familiar enough with them that a road trip wasnā€™t necessary. The central south has been calling to me for a long time, although Iā€™m still not sure what itā€™s saying.
I usually approach Kentucky from the north. It seems very southern compared to Ohio. This time, driving up from Mississippi, it seemed northern, its drawl flattened out to a midwestern twang. Either way, its identity is confused. This is where the great antislavery novel, Uncle Tomā€™s Cabin, was set. When Eliza struggled across the frozen Ohio River, she was literally leaping from slavery to freedom.
One-lane road, central Kentucky.
And yet, nowhere was ā€˜brother against brotherā€™ truer than in Kentucky. The state tried to sit out the Civil war, but its self-declared neutrality was ignored by both sides. Eventually, it cast its lot with the Union. But southern sympathies were strong, and a group of citizens formed a shadow government that joined the Confederacy.
I came to love Kentucky when I did art festival in Louisville. Now I take every opportunity to shun-pike through this state. It has beautiful farms, lovely steep hollows and hills, and the biggest known cave system in the world. But I was being a serious driver yesterday, intending to get from Bowling Green to Buffalo, NY in one shot. That meant sticking to the Interstate system like a burr on a saddle-blanket.
Dogwood and distillery.
Maybe it was the knowledge that there was snow ahead, but I couldnā€™t resist veering down the Bluegrass Parkway. This runs east to Kentucky horse country. These are the most manicured farms in America, and the horsesā€”even the ones free to graze near the roadā€”are beasts of singular beauty. The spring grass is in, and the horses were gamboling in the sun.
Before I got that far, I saw a sign for Kentuckyā€™s Bourbon Trail. That eventually put me on a series of one-lane roads. The blind corners, cropped hedges and small-town distilleries reminded me of the Isle of Skye.
Most of us, when we say weā€™ve ā€˜been toā€™ a place, mean weā€™ve driven through on the Interstate or weā€™ve flown in, gone downtown, eaten at trendy restaurants and seen a few tourist sites. You really donā€™t learn much about your country like that. Our common ground is to be found on the old Federal routes, at diners and city parks, in cypress swamps and little towns, at local church services, or talking to the guy at Home Depot. We should all do more of that.

This line of country

Google maps makes it possible to play cat-and-mouse in your car.
Parke County, Indiana, from an earlier midwest painting trip.
Most of my kids have Google maps location sharing set up. This feature tells you where a cell phone is. If I had younger kids, Iā€™d insist on it. However, my children are all adults. I donā€™t have them tied to my apron strings; it was something my husband was tinkering with and we never turned it off.
Itā€™s very useful, especially when someone loses their cell phone. ā€œMary,ā€ I can say from across the country, ā€œitā€™s at your house.ā€
Chapel of Faith, by Carol L. Douglas
I met my eldest and her family in Mobile, Alabama. Since then weā€™ve been traveling in parallel. They amuse themselves with tourist activities while I paint, and we meet up afterwards.
Location sharing has limitations. It updates periodically, not instantaneously. You can set a route to the last destination the phone was in, but you canā€™t track the other phone in real time. It will be less fun when they fix that.
Parke County, Indiana, from an earlier midwest painting trip.
My kids were poking along the gulf coast while I was in Langan Park with fellow painter Cat Pope. Rather than call them to meet up, I decided to track them. It was an exhilarating game, for they were moving as fast as I was. Time after time, I pounced, only to come up with thin airā€”theyā€™d moved on. Finally, they entered a cul-de-sac. ā€œAh!ā€ I said. ā€œI can cut them off at the entrance.ā€ But, alas, another car pulled up behind me, preventing my neat maneuver.
A warning, though: youā€™re driving a real machine, not an imaginary video-game car. Pull off to the side of the road to use Google maps, just as you should when doing anything not driving-related.
My son-in-law likes to drive at night. They headed north while I got a hotel room in Mississippi. Iā€™m a poor sleeper. I noted theyā€™d stopped for a while at a rest stop in Tennessee. In the morning, they were at the Corvette Museum in Bowling Green, KY.
Wabash Bottom Lands, by Carol L. Douglas
Rather than retrace my steps through Virginia, I decided to head north after them.
Theyā€™d stopped at a lonely country intersection south of Birmingham, Alabama for gas, about 40 miles from where Iā€™d been in Marion last week. There were two service stations. The first was devoid of life, except for a big olā€™ junkyard dog. Arthur lost his favorite cap running back to his truck.
At the second station, there appeared to be a party in progress. There were trucks everywhere, but nobody was buying gas. Nobody seemed to notice him. ā€œThey were like zombies,ā€ Arthur told me. He decided to go back to the first station. The dog was gone and the pumps were on, but the station was as ghostly and abandoned as ever.
As he headed back to the interstate, he saw something in the road. ā€œThatā€™s my hat!ā€ he exclaimed. It was full of bitemarks. He left it right where it was.

Goodbye, New Orleans

I had to leave you because of the beignets. We were developing one of those Southern Gothic relationships where they were trying to kill me.

Live oak branches, by Carol L. Douglas

I have to wear a fitted dress on Saturday, so Iā€™ve been scrupulously careful of my diet on this trip. Even in New Orleans, it wasnā€™t terribly hard, until the very last day.

Left to my own devices, I could have ignored the siren call of beignets, but other people kept handing them to me fresh from the deep-fryer. They were impossible to resist. When I realized Iā€™d eaten three of them in one day, I struck camp and headed out of town
ā€œYou should go to the county fair more often,ā€ my son-in-law told me. Beignets may ā€˜justā€™ be fried dough, but they taste somehow better here.
A fast sketch to understand the live oak’s branching pattern, which is chaotic.
I spent the morning painting the branches of live oaks at Audubon Zoo, which is in another beautiful old city park. Here the trees donā€™t have Spanish moss. Unlike City Park, Audubon Parkhas no meandering creek. According to a local, Spanish moss prefers to be near water.
Most trees spread their branches in some kind of regular pattern, including the white and red oaks of the north. Not so with their southern cousin. The live oakā€™s branching pattern defies visual organization. Itā€™s as sinuous and baroque as everything else down here. Eventually, the branches end up dipping right back down to the earth.
My friend’s former home on Arabella Street.
I drove down Arabella Street to take a photo for a friend. She once lived in a lovely small house here and was curious to see what it looked like today. Iā€™d say it was spruce and pristine and gentrified, although theyā€™ve taken down her porch swing. A Whole Foods now occupies the site of the derelict bus station from her day.
The streets in New Orleans are atrocious. On Magazine Street, I narrowly missed a giant pothole that was deeper than my wheel is tall. A local had helpfully made a big sign on a cardboard box: ā€œFā€™ing Huge Pothole!ā€
Spanish moss in City Park.
That afternoon, I went for a long walk through City Park to stretch my legs. Thereā€™s so much more to paint in this city, including the shotgun houses and Creole cottages. Next time I paint here, Iā€™m staying for a week. Now, however, I have to be in Buffalo on Saturday. Itā€™s time to put my sneakers back on and head north. I hear there are four-foot drifts in my driveway.
One of my tasks for this trip is to try out sketchbooks for my Age of Sail workshop. (Materials are included.) I like the paper in this Strathmore one, but the binding is making me a little crazy.
On my way out of town, I stopped at a Winn-Dixie in Slidell, Louisiana. There I bought carrot sticks and hummus. Oh, and some beignet mix for when I get home, just in case.

This painting isnā€™t as bad as it looks

Actually, it was pretty much a failure, but I will try again today.

Gator pond, Gulf Islands National Seashore, Ocean Spring, Mississippi.
When I was in the Bahamas in 2016, I was fascinated with palms, a family of plants with more than 2000 members. I meant to be fascinated with them on this trip, too. Instead, the southern live oak has captured my heart.
These are not true evergreens. Rather, like young beeches and oaks up north, they drop their old leaves immediately before new leaves emerge in the spring. The difference is that the old leaves remain green right up until the swap, whereas our northern ones dry up and rattle in the winter wind.
This week, the new growth on New Orleansā€™ live oaks is emerging. That leaves the branches denuded of their characteristic heavy, dark covering, allowing their parasites to dominate the scene. These include ball moss, Spanish mossresurrection fern, and mistletoe. The trees seem to tolerate them, but they make them look more gnarly than they actually are.
Spanish moss at Mobile Bay. (Photo courtesy of Douglas Perot)
There are countless examples of ancient live oaks here in New Orleans. They have weathered terrible storms for many decades.
On Sunday, we made the drive from Mobile to New Orleans through a heavy rain. My intention was to paint at Davis Bayou at Gulf Islands National Seashore in Mississippi, but the rain drowned all visibility. I did this little sketch of a gator pond before the lightning drove me away.
Louisiana ‘s wild alligator population is estimated to be around two million. Apparently, thatā€™s not enough, because there are an additional 300,000 farmed alligators here. That, I think, means youā€™re likely to see one anywhere thereā€™s water. I imagine theyā€™re relatively torpid right now. Daytime temperatures are the low sixties. Still the sunā€”when youā€™re in itā€”is hot, and reptiles love sunbathing.
Live oak and folly (unfinished) at City Park.
I set up to paint in City Park. This has a wonderful botanical garden, great swathes of trees, meandering creeks, and the additional attraction of the Morning Call coffee stand in the old casino. It was, however, unwise of me to choose a backlighted tree with a domed, columned folly behind it. I spent the morning cheerfully drawing the building and trees and started to limn in the colors when two things occurred to me. First, I was unbearably hot, and second, the light had turned. My backlighting was no more.
Fewer beignets, more painting time!
I gave it up and decided to go down to the historic district to find some lunch and the waterfront. What I thought might be a two-hour jaunt used up the remainder of the day.
ā€œDuring the week, especially in Manhattan, the pace is so slow, you often feel that any mode of transportation might be as fast as any otherā€”you could walk, drive, take a cab or ride the subway and get there about the same timeā€”so we choose our transport more on aesthetic grounds,ā€ Garrison Keillor once said.
The same seems true of New Orleans. I raced my traveling companions back to City Parkā€”they on the trolley and on foot, me in my car. We arrived back at exactly the same time.

Monday Morning Art School: how to draw windows and doors that fit

 The South sure loves its Greek Revival pillars, doors and windows. Hereā€™s a little trick to draw them evenly.

My painting of Siloam Baptist Church from last week.

The South also observes Blue Laws. That meant I wasnā€™t able to get a replacement sketchbook at Hobby Lobby yesterday. I drew these on tissue paper; the quality is terrible.

Earlier, I taught you how to draw a door in basic perspective. The door makes a shape called a trapezoid. (Donā€™t be frightened; thatā€™s as mathematical as weā€™re going to get here.) When drawing buildings, most people get basic two-point perspective right but then mess up in spacing windows and doors. Hereā€™s a technique you can use to divide the face of any building into regular units, no matter what angle you are looking at it from.
Dividing in half
Just draw an X from corner to corner. The vertical line that runs through the middle of this X is the center of your building. This is very useful for buildings, because if thereā€™s a pitched roof, it almost always comes down from that center point.

Dividing into thirds

Draw a star shape, starting from the bottom outside corners and running to the top-middle and the top-outside corners.
Do the same thing, upside down, so that you have a six-pointed star.
The points where the lines intersect are the thirds.
Dividing into fourths
This requires that you figure out the middle of one side of your trapezoid. Then draw a line between it and the middle-point. Now you have the horizontal center-line. It will not be level; it should hit both sides at the mid-point.
Draw your star-shape again. The points where it intersects the center line are the quarters.
Dividing into fifths

This is the most complicated and fun of the divisions. Start with a horizontal center-line as you did above.
Now youā€™re going to draw some crazy diagonals:
  • From the bottom left corner to the top middle.
  • From the bottom middle to the top right.
  • From the top left to the right middle.
  • From the middle left to the right bottom.

The points where those diagonals meet are the 1/5 divisions.
In practice you can divide and subdivide these units to figure out the placement of windows and doors pretty quickly. Here is my division of Siloam Baptist Church, above (yes, the bottom line was wrong; I fixed it after I took this photo):
And here is a fast division of my first drawing. I just broke the units I had into smaller ones using the same principles:
Which I then extrapolated into this purely imaginary facade of a house:
I didn’t do any of this with a ruler, but with another piece of paper as a straight-edge. Once you learn these divisions of space, they take only seconds to do. They are much easier than guessing and erasing.

The old South and the new

An Alabama folk artist will know heā€™s made it when his work graces the walls of a Manhattan apartment, even if he doesnā€™t see much cash from the sale.

An outdoor folk art installation in the woods.

The Confederate Cemetery at Marion is full of Union soldiers who died in hospital here. They outnumber their southern brethren, in fact, with whom theyā€™re buried side-by-side. It was just one of many surprises here in Perry County. This is the second-poorest county in Alabama, which is itself the 47th poorest state in America, but itā€™s also a proud and beautiful place.

ā€œThereā€™s art in these woods,ā€ our guide, Pastor John Nicholson of Siloam Baptist Church, told us. Sure enough, tacked to the trees were paintings on pieces of old tin roofs. ā€œThere used to be lots more,ā€ John lamented. I hope that a gallerist doesnā€™t discover this open-air gallery any time soon. Then, instead of being free to the citizens of Marion, the art will cost $20 for Manhattanites.
Cypress swamp in Perry County, Alabama.
In the bigger world, money conveys legitimacy. Earnest Williams isnā€™t making any money by tacking his paintings onto trees. When his paintings sell for six figures and grace the walls of an Upper East Side classic six, heā€™ll know heā€™s arrived, although he will probably see very little actual cash from it.
The UN instructs us that Alabama is practically a third-world nation. My husband was in Haiti a few years ago. ā€œDoes that look like Haiti?ā€ I asked him as we passed a particularly ramshackle cabin.
ā€œPerhaps like the very best house in Port-au-Prince,ā€ he answered.
Antebellum house in Marion, Alabama.
I do know the slums of Rochester pretty well, and measure for measure, I’d rather be in the woods. New York ranks 15thin America for wealth but right behind the District of Columbia for income inequality. Iā€™ve known plenty of people living in a different kind of squalor. If your neighbor is a snapping turtle or black bear, youā€™re already wealthier than the family living next to a drug house with a chronic rat problem.
There is a lovely antebellum house mouldering on Marionā€™s main street. This is not because of poverty, but because of family dynamics; the owners are alive and prospering just around the corner.
Old slave housing in Marion, Alabama.
A sermon or seven could be preached about this houseā€™s fall from grace. Camellias of every variety bloom in its overgrown lawns. Its slave quarters stand as they did in the 19th century, as does its outdoor kitchen. For the first time in years, Iā€™m motivated to paint something overtly instructive. I took many, many photographs. ā€œYouā€™ll just have to come back,ā€ John said.
South of town, the landscape is less woodsy and more prairie. We stopped by a lovely old farmhouse in the middle of pasturage, lakes and ponds. It would be the perfect place for a workshop. Iā€™m seriously thinking about it.
Camellias in bloom.
I stopped in Montgomery for lunch. This is more like the New South Iā€™ve read about, a 20th century boom-town, with bustling restaurants and souvenirs in its riverfront area. A tour guide cheerfully herded her charges down pavements that once served as Montgomeryā€™s slave market.
Thereā€™s a small industry here in Hank Williams remembrances, with people picking over the details of another poor Alabama boy’s life. Iā€™m a fan, so we dutifully forked over our $20. A swank tour coach from Georgia was parked next to his grave. 
Next stop, Mobile.

Alabamaā€™s black belt

A sleepy exterior belies a turbulent civil rights history.

Siloam Baptist Church, by Carol L. Douglas.

In the earliest days of social media, ā€˜stranger dangerā€™ took the form of warnings about people on the internet. When I befriended a Southern Baptist preacher online, my kids were horrified. Facebook came along, and Pastor John Nicholson posted photos of Marion, AL, and historic Siloam Baptist Church. He told me that I really ought to come down and paint there someday. Yesterday, I did.

The city of Marionā€™s population is about the same as that of Rockport, ME, but it is able to spread out on a neat grid of streets. There are some terrific, large, old houses here, and like everything else, they have elbow room. The pastorā€™s home is a massive old place; so is the church itself. Built in the boom times, it could seat five hundred worshippers.
The chair of the art department at Judson College told me a little about this area’s civil rights history, and gave me this book.
This is the center of Alabamaā€™s Black Belt. This originally referred to the region’s rich, black topsoil. With the development of 19th century cotton plantations, the term started to refer to African-American slaves as well. After the Civil War, freedmen stayed as sharecroppers and tenant farmers. Perry County, of which Marion is the seat, is almost 70% black.
Jimmie Lee Jackson was a young civil rights activist and deacon at St. James Baptist Church here in Marion. On February 18, 1965, he was beaten and shot by troopers while protesting. Eight days later, he died in hospital in nearby Selma. This was the catalyst for the first Selma to Montgomery March on March 7, 1965.
Jimmie Lee Jackson’s home church in Marion, AL.
Itā€™s hard to resolve this sleepy, pretty town with such a violent and important history. In fact, I didnā€™t know anything about it until I met Joshua Pickens, head of the art department at Judson College. This small, jewel-like school was founded by members of Siloam Baptist Church in 1838, making it the fifth-oldest women’s college in the United States.
My maritime buddies might appreciate the sentiment.
I was there to talk to his students. After, they showed me a formal room in the front of Mead Hall. This is a combination parlor and dining room. It dates from the days when etiquette was an important part of a womanā€™s education. Even the beautiful old china is still there.
Siloam is a mother church of the Southern Baptist Convention.
Siloam Baptist Church itself has a strict, austere Greek Revival symmetry. Had I the time to do a second sketch, it would be of the doors behind those squat Doric columns.  Seldom used now, they led to the sanctuary and to the gallery, where slaves (and later, cadets from Marion Military Institute) sat.
That evening, I joined the Siloam church family at a church supper. The college-age Bible study was lightly attended because itā€™s midterms, but there were still more than a dozen young people. They recounted Old Testament history, sang hymns and then discussed Scripture for an hour and half. It was far more rigorous than any church school class I ever taught. The Black Belt may be financially poor, but they have a rich spiritual legacy, and theyā€™re tending it.

Ridge running

Chattanooga seems unchanged since last time I was here, in, oh, about 1972.

Blue Ridge overlook on a late winter day, watercolor sketch by Carol L. Douglas

I can drive from Rockport, ME to Chattanooga, TN on less than $90 worth of gas. Thatā€™s the beauty of a Prius. But at more than 250,000 miles, my car is growing delicate, even though I attend to every rattle and gasp.

I spent the night near Sherando Lakein Virginia. I know this area well. GPS would have looped me north and back to US 81. Instead I headed south on Virginia 664 until it dead-ended at the Blue Ridge Parkway.
That was a good plan until my brake started dragging. I was out of cell range and miles from any services. I am carrying no tools, not even a screwdriver. Itā€™s the off-season, so we were absolutely alone except for a few white-tail deer that bounded across the road. Even the black bears are still hibernating, not that theyā€™re any more skilled at brakes than the deer.
It was dark and bleak, and then it started sleeting.
I prayed fervently and hit the brake pedal. Last time I did thatā€”in populous Ryeā€”a brake shoe fell out. This time it worked like it was supposed to. The brake sighed happily and gave me no more trouble. Vastly relieved but still a little anxious, I continued along that lonely ridge. It is one of the most beautiful roads in America, a long, skinny park with very few access points.
The mountains were unusually bleak. Usually they stretch to the horizon in billows of blue, growing lighter and lighter as they get farther away. But it is still winter, and the sky was gloomy. At this elevation, there were no tell-tale signs of springā€”no green haze in the understory, no red buds on treetops. The ridge sits and pouts and waits for warmer weather.
I was planning on turning here anyway.
I found an overlook and did a watercolor sketch. It started to rain as I finished. The temperature was hovering at the freezing mark, I bent and felt the pavement. Slick.
The rain turned to sleet as I worked my way carefully south. At Route 60, I turned to the west and down off the mountain. It was a relief to pick up US 81 again.
The Blue Ridge Parkway on a less grumpy day.
The first (and only) time I was ever at a tent meeting was at Lookout Mountain in Georgia. The North in the late 1960s was much too decorous for that kind of exuberance. The meeting started at sunset, and I remember it as a beautiful place, bathed in golden light and with a terrifying, difficult topography. It all seemed wonderfully exotic to a young, unchurched girl from New York.
Iā€™d hoped to make Chattanooga in time to detour back to Lookout Mountain. I remember that the mountain has a commanding view of the Tennessee River. It was beautiful, and it was also what made it strategically important during the Civil War.
Alas, it was not to be. Traffic around Knoxville was as dense as Queens Boulevard at rush hour. I was stuck.
My late cousin Joy, left, my late father, and me.
I arrived in Chattanooga as dusk fell. This city has always reminded me of my hometown of Buffalo, NY. I could almost, I thought, strike off and find my cousinsā€™ old house. My cousin Danny would be careening around on his unicycle in the stifling summer heat, and his sister Joy would greet us at the door with a crackinā€™ loud ā€œHi, yā€™all,ā€ while a passel of little kids milled around. 
But time doesnā€™t go backwards on its reel, Iā€™m afraid. Dan is the only one left in Chattanooga; the rest are scattered by time and distance. So I turn my face resolutely south to Alabama and whatā€™s called me here.

Where America came to die

Iā€™ve been in every state except Hawaii, and most Americans have seemed smart, informed, and good-natured.
Shenandoah Valley, by Carol L. Douglas, from a prior trip.
ā€œThe south,ā€ in American parlance, isnā€™t a geographical distinction. Rather, itā€™s a political distinction. Those states that seceded in 1860-61 are ā€œthe south,ā€ and the rest of us are ā€œthe north.ā€
Iā€™m heading south, but I donā€™t intend to start my poking and painting properly until after Chattanooga. Still, I occasionally exit the interstate in places where the landscape means something to me.
Old Federal Route 11 is the historic highway that US 81 largely supplants. At Chambersburg, PA, it crosses the Lincoln Highway. Thatā€™s one of the earliest transcontinental highways, built in 1912-13. Years ago, I painted my way north through Virginia and Maryland to Dauphin County, PA, with a tent and my little dog Max, who was just a youngster at the time. Much of that trip was spent on the Civil War battlefields of Northern Virginia.
Campbell’s Field, by Carol L. Douglas, was painted in Dauphin County, PA.
The Shenandoah Valley is one of those places that calls me inexorably off the road. This has nothing to do with the valleyā€™s natural beauty, which is considerable. Because of its strategic importance it was the scene of many bloody engagements in the Civil War. That history can be compressed into two armies chasing each other up and down the length of the valley. Finally, in the fall of 1864, Phil Sheridan cleared Jubal Early out, once and for all, with a scorched-earth campaign that foreshadowed Shermanā€™s March to the Sea.
Yesterday, I drove slowly along the verge at Cedar Creek Battlefield and up a side road to Belle Grove Plantation. Nothing has changed since I was last here in 2014. Cows graze on the battlefields, and the plantation house sits in rather bleak splendor. Still, you canā€™t pitch a penny in this countryside without hitting a spot where some American died, violently.
Why was General Sheridan so ruthless, so effective, compared to the generals who went before him? The answer, I think, lies in our deep reluctance to hurt our fellows. Finally, after the election of 1864, the American public had had enough. Sheridan and Sherman (and Grant, of course) had the license to wrap it up.
It was a driving day yesterday, but I couldn’t resist doing this one small sketch, Early Spring in the Shenandoah Valley.
Four years of intense combat left 620,000 to 750,000 people dead, in a nation of 31 million people. Itā€™s no wonder that their voices seem to call from every rock and spring in Virginia.
Imagine what that would mean with our current population: between six and seven million casualties.
Every time we casually drop terms like ā€œlibtardsā€ or ā€œdeplorablesā€ to describe our political opponents, we contribute to the same kind of hatred that led to Senator Charles Sumner being caned in the well of the Senate, and from there to civil war. We face issues now that bite at the nature of our Union, the same way slavery bit at our union in 1856. Can we solve them without establishing new killing fields?
Iā€™ve been in every state except Hawaii, and the people Iā€™ve met have been smart, informed, and good-natured. Cultivating peace starts with cultivating respect.

Monday Morning Art School: How to paint from a moving vehicle

If you have room for a cup of coffee, you have room to paint.

I finished this sketch as the sun finally set.

I painted across Canada (the first time) in a corner of an overloaded Suzuki Grand Vitara containing four people and all my daughterā€™s earthly belongings. Compared to that, the passenger seat of my Prius is downright spacious.

You will need a plastic cup, water, a small watercolor kit and a watercolor sketchbook. That will all fit in a roomy pocket or a purse.
You should be carrying water when you drive. The plastic cup is just a refinement.
ā€œBut the scene is constantly changing!ā€ you say, and youā€™re right. Youā€™re going to generalize rather than draw a specific moment on the road. This teaches us about composition and reducing our paintings to their essentials.
You canā€™t paint while driving, any more than you can text. (I would think this goes without saying, but apparently there is no idea so bad that someone wonā€™t try it.) This is why I ended up doing this painting on I-495 instead of on scenic Route 1. It was my turn to drive during the interesting parts.
This was the road I chose to demonstrate this technique. Not a Scenic Byway.
I-495 is a contender for Americaā€™s most boring road, except when traffic stops and it becomes one of our most irritating roads. Yesterday, its monotony was compounded by a gloomy sky, the tail end of last weekā€™s Norā€™easter. Thereā€™s a lesson in that: you can find beauty anywhere, if you look for it.
I start car paintings by studying the passing scene. What is the line or motif that is most commonly repeated?  In some cases, itā€™s the pitch and roll of the hills. In others, itā€™s the way farm buildings sprawl down hillsides. 
A generalization of the passing scene.
Usually, I look out the side window, at about the point where old cars used to have vent windows with little cranks. That gives you a view of something other than the road, while still being comfortable.
However, in eastern Massachusetts the trees grow right up to the verge. You must look forward, straight down the road. The dominant motif is the stands of trees, and the question is how they interrupt the skyline. There are occasional hills in the distance, and there are other cars.
This was the point when I realized I left my pencil on my dining room table. Itā€™s easily replaced, but not on a freeway on a Sunday evening. Miraculously, we stopped at a rest stop and parked next to a pencil stuck in the mud. Cleaned up, it was perfectly serviceable.
Some light washes in place. I would normally use a different brush, but I want to demonstrate that this can all be done with a kit that fits in a pocket.
I needed that pencil, because I always start with a line drawing incorporating those iconic features of the landscape. A light wash established the drear of the sky and the hill in the distance. I used the tiny brush from my field kit to make the point that you donā€™t need a lot of tools for this. This brush is great for fine lines, but it doesnā€™t make good washes. I laid it on its side and scumbled the grey sky in instead. If I were using a juicier brush, Iā€™d have run the sky below the tree line.

My pocket paint kit. You can make one out of an Altoids tin but unless you already have the paint, buying the pre-made one is actually cheaper.
Every watercolor painting needs a test sheet, because watercolor is all about density control. Luckily, you can test on the reverse of a prior page. It won’t hurt the painting on the other side. Or, if you want to conserve paper, stick a loose sheet in there and move it around as you need it.
You always need a test sheet, even when you’re messing around.
When it comes to observing details, the repetitiveness of the freeway helps. When I need a stand of spruces, there is always one more just up the road. There are dormant, deciduous trees everywhere, and Massachusetts has no shortage of rocks.
Of course, you’re not going to paint fine lines unless you’re stopped in a traffic jam. The roads in the northeast are too jarring for that. Thus, my taillights are just a suggestion, dripped onto the paper at the last minute. I finished just as the last light faded from the sky.
St. Elias Mountain Range, Yukon Territory, painted from a car in 2015.
This is a technique you can use to amuse yourself anywhere you have at least 40 minutes to killā€”in a car, a train, on a plane. Itā€™s the basis of our sketchbook technique for our Age of Sail workshop, except weā€™ll be concentrating on water instead of pavement. Of course, Penobscot Bay is also much prettier than a Massachusetts turnpike.
I’m on the road to Alabama and points west this week. Tonight’s destination is the lovely Blue Ridge Mountains of Virginia. Stay tuned to this spot to follow my travels. (Or subscribe above; itā€™s probably easier.)