Sophie Leiter


A Bootlegger’s Story


In the 1770s they were revolutionaries, the ragtag band of boys and men that captured Fort Ticonderoga. In the 1790s they became Americans. From 1810 to 1840 they raised sheep, merino wool before it was hip. They carved their farms out of the thick forest. They ran white pines and oaks down roaring rivers. In 1860 they went south to fight for Lincoln, against an institution they outlawed 90 years before. The ones that stayed grew hops. They raised cows and tapped maples. And in the 1920s, during Prohibition, when the dairy farms were going under and the big timber had all been felled, they smuggled alcohol.

They made it in stills sitting in cold springs and streams, hidden away in the mountains. They brought it down from Canada in rowboats over Lake Memphramagog, careful to avoid the Mounties in motorboats. They raced away from arrest in souped up Model Ts, Packards, Lincolns, and occasional Cadillacs with lights off, up and over windy mountain roads. When Prohibition ended, and the need for fast cars and their drivers had diminished, they turned to stock car racing, which eventually became NASCAR. They began smuggling to and from Canada in 1807, with the passage of the Embargo Act. They smuggled everything, from timber to blankets, but it is alcohol they are famous for.

Who are they? They are Vermonters, the men (and a few women) who came before me, my forebears in adventure. Some had beards and some were clean-shaven. They wore suits, or uniforms, or coveralls. They protected their families and their communities. They were independent, fierce minded, resourceful, and determined. They did things their own way. It is their spirit I honor and their footsteps I plan to follow.

Vermonters have always had an affinity for alcohol. Spirits, beer, and cider are inextricably tied to the type of outdoor hard labor that so characterized the early years of statehood. Loggers, farmers, militiamen all favored a sup after a hard day’s labor. Taverns were the center of community life. The Green Mountain Boys routinely met in one to plan their daring deeds. The constitution of Vermont was signed in a tavern. Though they had laws in place to prevent “excessive consumption” the average Vermonter, especially the average male Vermonter, consumed what many today would consider an excess of alcohol.

Between 1790 and 1820 distilleries exploded across the state, to the point that by 1820 there were more recognized distilleries than recognized towns. With the increase in production and consumption, many pro-temperance groups sprung up, stating concerns for declining morality and farm production in the state. A series of laws began to tighten restrictions on the production, consumption, and sale of alcohol within the state and by 1853 Prohibition became the state law. Support for the law was split East-West down the state, with the western counties favoring Temperance.

Enforcement was loose and irregular. Nearby states remained wet, making it easy to cross state lines to drink or buy alcohol. With borders on four sides to wet states (or Canada to the north), smuggling was rampant. The law was constantly being altered after contentious court cases and many felt that the loss of tax revenue from the sale of alcohol hurt the state. Fewer tourists were coming to the state and many inns and taverns were struggling. Hops farmers were forced to switch over crops, resulting in economic losses and increased labor costs.

In 1902 mounting anti-Temperance pressure led to the passage of the Local Option, an alcohol law that left decisions on the production, consumption, and sale of alcoholic products up to individual towns. Temperance still had considerable support, especially among women, and in 1919 the anti-Temperance Vermont governor, Percival Clement, chose not to ratify the 19th amendment giving women the right to vote, for fear that they would re-establish Prohibition in Vermont. Vermont eventually did ratify the amendment and mere months after that, Prohibition became the law of the entire country.

Under Prohibition smuggling became a professional operation. Small-time local bootleggers were now competing with crime syndicates from Boston and New York. Unsubstantiated rural legend is that Al Capone himself spent a night in North Troy to oversee the smuggling operation. Much more alcohol was moving over the border and much more money was being made. Most of the alcohol was bound for Boston and New York City, but some made it to local speakeasies and line houses (houses that straddled the border allowing patrons to drink in Canada, where it was legal.) Very few locals got rich off of smuggling, but many were able to make enough to save their farms, which had been failing in the Great Depression.

A typical load consisted of ten cases of beer, generally Molson or Genesee, and one case of liquor. The loads would usually be driven to Barre, either down 108 and over Smuggler’s Notch or from Highwater, Quebec through Newport, VT, and then distributed south to Boston and New York City. Smuggler’s Notch separates Mt Mansfield, the tallest peak in VT, from nearby Spruce Peak. After the Embargo Act of 1807, it became a popular route for smuggling goods to Montreal. Many runaway slaves used it as an escape route to Canada and until the route was paved in 1922, many locals even herded livestock through to sell in Canada. The paving of Route 108, the road that goes through the Notch, made it an even more popular route for smuggling, but this time for alcohol. The many caves throughout the Notch provided a perfect place to store alcohol and hide from police.

Police officers were not able to keep up with the faster, modified cars the smugglers drove and often resorted to driving the vehicles they had confiscated from other rumrunners to chase them down. Once the police caught on to the driving routes, many rumrunners switched to boats on Lake Champlain and Lake Memphramagog. Some went for quiet and unassuming boats, like canoes or rowboats, and others went for souped up motorboats, suitable for quick getaways. In the winter, smugglers were known to drive their cars out on frozen lakes to elude the police. There are even some accounts of smuggling alcohol on horseback over the border or into remote logging camps.

After Prohibition ended in 1933 the smuggling business died out. The end of the Great Depression saw farms bounce back and World War II brought jobs and economic prosperity. Nowadays-cheaper alcohol prices in the US mean that alcohol is actually being smuggled in the opposite direction, to Canada, though on many of the same routes. The local bootleggers and moonshiners are mostly gone. Their mark on the state, however, remains.

I will follow their path up to Canada, Bedford, to be exact. I’ll fill my pack with Molson beer and Seagram’s whiskey and bring it down the old route, through Smuggler’s Notch. It’s an insignificant amount of alcohol and an unremarkable ski. The adventure, in this case, is about the route.

Smugglers, beginning in Frehlighsburg, Quebec, would follow 108 all the way through the Notch and into Stowe. From there they’d bring it to Barre, via a few possible routes, where it would be collected and taken to Boston and New York. I’ll follow that route as far as Stowe, but since 108 is closed from Cambridge to Stowe in the winter, I’ll have to ski the last bit. I’ll drive a Subaru, not a Model T and I don’t expect to be followed by any customs officers. I’ll end my route not in Barre, but in Middlebury, because as much as I believe in symbolism, I don’t believe in unnecessary 125 mile, three hour drives.

I suppose I’m searching for something that seems missing, some enduring piece of history that seems to be shrinking. We don’t run rum anymore. Dairy farms are slowly dying out and the land is bought up by wealthy out-of-staters, the farmhouses gutted and remodeled. Tight-knit communities like the one I grew up in are breaking up, community picnics and the town broomball league just quaint anecdotes of a pastoral past. There is a line from my favorite short story, Where the Rivers Flow North, by a Vermont author, Howard Frank Mosher about a man who has outlived his time, that has inspired the emotional component of this adventure,

He looked up on the ridge at the soaring pines and realized that he had found what he did not even know he had been looking for, some enduring fragment of the original wilderness.

I want to honor the part of me that has always felt shaped by the state. Out-of-state friends always tell me I am “so Vermont” because I drench my pancakes in maple syrup and have a taste for Carhartts. I want to go beyond that, to do something the hard way, to go against the grain, to honor the “real Vermonters”. I want to find them, to know them, to be them. But I don’t have any right. I’m a local, but I’m not a native. I get to view this life from nearby. I romanticize it without ever having lived it. So I’m trying to live it. With perhaps the most romanticized account of smuggling ever written, Disappearances by Howard Frank Mosher as my inspiration, I’m going to drive to Canada and smuggle some alcohol to the thirsty denizens of Middlebury, VT. I’m setting out to find “some enduring piece of the original wilderness” in me.


The night before our adventure passes in a flurry of texts. My plan is to drive up to Canada with my friend Atticus and two more friends, Cole and Pete, will meet us at Smuggler’s Notch. Both are fellow ski patrollers and my tele club compatriots. Cole has never been one to turn down an aerobic adventure and Pete has never been one to turn down a beer. Their plan is to meet us on the Cambridge side of Smuggler’s Notch and ski it with us. I feel the burden of everyone’s experience on my shoulders. I want to tell them it might not be fun. It won’t be a really cool ski. It’s a 90-minute drive for a nice walk. They asked to come though, so instead I just remind them to bring snacks.

I wake up at 6:30 to a text from Atticus: “Soph, I’m going to have to be a no today. I’ve had a fever and chills all night.” I guess I’ll be driving to Canada alone. I eat breakfast alone and pack myself a small lunch. I don’t really know how long this will take. I think I’ll be back by dinner… I make another PB&J. I throw my things in the backseat of my car, no need to be organized if it’s just me. With my feet hovering over the clutch and the accelerator, I take the plunge, and point it north.

The drive passes uneventfully. I’ve decided to go to Canada via route 89. It isn’t historical, but it is faster. As the exits thin out the land seems to get grayer. There are fewer and fewer buildings and more marshes and fields. The day is overcast and the scenery does little to lighten the appearance. It is drab and barren but I can’t help but feel affection for it.

As I start to see signs for Canada my heart starts beating faster and faster. I’ve rehearsed what I’m going to say to the officer. Advance readings of customs procedures have scared me into the strategy that the truth, however strange, is the best way into the country. When I pull up to the window, I am surprised to see someone about my age. He has a prominent brow and dark eyes. He looks perfectly at home in his dark turtleneck uniform shirt, which gives him the appearance of a young Bond villain.

“Where do you live”?

“Norwich, Vermont”.

“What is your purpose for entering Canada today”

Deep breath. “I’m doing a project on Prohibition era Vermont and I’m retracing and old smuggling route so I have to start in Canada because they used to smuggle alcohol from Canada down through Vermont” This rambling mess is not the script I rehearsed, but my crippling fear of authority took over. He gives me a searching look, finding a nervous college kid with a weird idea, and probably lamenting the fact that he ended up working customs on the border of one of the strangest states in the US, he lets me go after a few more procedural questions.

I had previously saved directions to the nearest liquor store on my phone, knowing that my phone wouldn’t work across the border. What I hadn’t thought to check was whether or not the average liquor store carried what I was looking for. There is no Molson, Genesee, or Seagrams in sight. In a hurry to meet Cole and Pete at the trailhead and wary of the French speaking Quebecois, who generally look down on their southern neighbors, I buy the only Canadian beer I can find and the tiniest bottle of whiskey in the store.

Though I’m driving back a different way, so as to more authentically trace the route, the scenery looks the same. The only difference this side of the border is the language. The sprawling farms still look faintly dilapidated, as though peeling paint were an infection spreading to every part of the operation. There is a sense of radical rebellion in their existence, however. “We’re still here” they seem to cry out. That unruly spirit remains untamed both sides of the border.

My re-entrance into the United States goes much smoother. Another officer about my age, with a much kinder visage, giggles when I hold up a six-pack and ask if I need to declare it. He ushers me through quickly, assuring me that the tiny amount of alcohol in my car is not worth their time. When I pull in to the makeshift parking lot at the end of Route 108 before it enters the Notch, I am relieved to see snow. The barren fields in Northern Vermont had not inspired confidence in my ability to pull off the skiing part of this mission. I spot Cole’s car and raise my eyebrows as he exits alone.

“No Pete?”

“No Atticus?” He responds with a smirk.

“Fever” We both shrug and start putting on our snow pants. Others in the parking area are gearing up for ice climbs and big skis. I feel a little silly, filling my backpack with beer for a casual jaunt in the snow, especially when others are carefully packing ice screws and ropes for ice multi-pitches. I feel even sillier filming myself do it. I try to shrug off the glances from other adventurers as I fiddle with the camera. I feel narcissistic and self-important filming myself, but I steel myself for the sake of the assignment.

We begin ascending, passing road signs for falling rocks and narrow turns. Cole is a competitive bike racer, but kindly skins next to me at my pace, as I breathlessly fill him in on all my research about smuggling in Vermont. The entire snowed in section is only three miles with very little elevation gain or loss. Even at my pace, we quickly reach the top of the Notch, and rip our skins for the mellow ski down. I have to jostle around the cans of beer to fit my skins in my pack. I’m going to have to drink these soon. Why did I feel it was important to drink them? I don’t drink, for a number of reasons, but the one that continually keeps me away from alcohol is the taste. I find it repugnant.

All too quickly we’re in the flats near the bottom of the Notch. After four big, windy turns, we’ve lost all of our elevation. “Speed Limit 40” signs seem to taunt us as we skate the last ten minutes on flat ground. I imagine driving this road at high speeds, without lights, as I know they did, and decide I’m happy on skis in daylight. As the end of the Notch comes into sight I spot my friend Tucker. He’s skiing at Stowe for the day and came to meet us to witness my first beer.

Wasting no time I pull the beers from my backpack and my knife from my pocket. Tucker shows me how to tilt the beer, so that there is an air bubble near the bottom of the can. I puncture the can, and he widens the hole out with his thumb. I know the routine, having watched a number of my friends carry out the same ritual at parties. On three we click open the cans and pour the beer, or in my case most of the beer, down our throats.

“Oh, that is not good…I don’t like that”. Both boys chuckle, having finished their beers full seconds before I did. They tell me I bought the wrong kind of beer; you’re not supposed to shotgun a pale ale. “Molson would be better”. You’re telling me. I don’t make them do the shot with me. It’s not even Canadian whiskey because I couldn’t find any. I fill up a capful of Fireball cinnamon whiskey and suck it down. “That was worse than the beer”, more chuckling. As we re-pack to head back to our cars I unsuccessfully try to wash the taste away with chocolate covered pretzels. They both tell me I’ll never learn to like alcohol if I try it this way. That wasn’t the goal. Not trying the alcohol felt inauthentic. Having tasted it, I don’t feel the need to have anymore. Vermonters are stubborn and I’m embracing that spirit.

The way back is uneventful. We’re both less talkative, partially because I’m trying to suppress beer burps, but also because we’re both scanning the trees, scouting potential lines for our next ski trip. I lose myself in thought, running through everything I know about smuggling, wondering how I stack up, and we’re quickly back at our cars. The sun has dipped behind the mountains and with sweat freezing on my back, I wave to Cole, jump in my car, and blast the heat. Even though I’m no longer tracing a historic route, I decide to continue taking back roads. They’re better for thinking and better for seeing the land I’m trying to reconnect with.

I grew up here, but I can’t really call myself a Vermonter. That title is reserved for those whose grandparents were from here. I may have lived here my entire life, but that doesn’t change the fact that my mom is from Massachusetts and my dad is from Kansas. I also, technically, wasn’t born here. The nearest hospital to my parents’ house was in New Hampshire, so that’s where I was born. They quickly brought me back on the right side of the border, but these things matter.

Both of my parents came to the area for college. My mom went to Middlebury and my dad went to Dartmouth. Besides a brief stint in Rochester, NY for my father’s medical residency, they have spent their entire married life in Vermont. More than thirty years ago they bought a run-down farmhouse on 18 acres in Woodstock, VT and until 2 years ago, that was the only house I’d ever known. The property had one house, a chicken coop, a sugarhouse, and a barn. When I was about 10 the barn fell down because we didn’t shovel the snow off the roof fast enough. The whole structure just toppled and folded diagonally. The previous owner’s wife had been diabetic and confined to a wheelchair on the first floor. When they bought it no one had been upstairs for years. Floorboards were rotting and the walls were more of a suggestion of a barrier than any real protection from wind and cold. Over the years they fixed it up, doing most of the work themselves. For years they raised sheep, sending the raw wool to a collective that sent back spun yarn. When they had my sister, and eventually me, they got rid of the sheep. Two kids, two jobs, and 30 sheep are a lot for two people, and sheep are easier to sell than kids.

My parents are old school. They’re part of a generation that moved to Vermont to reclaim a sense of community that was slowly leaking out of suburban America. They were chasing a different kind of American Dream, one where you don’t have a white picket fence, because you don’t want to feel divided from your neighbors. They lived in the same house for 30 years and when they finally did move, it was to a more secluded, more run down-farm with even quirkier neighbors. This move, after 20 years in the same house, left me shaken. I felt untethered. To quote the Vermont State Anthem, These Green Mountains “They say home is where the heart is…”, but my heart seemed to be split between the place I grew up and the place my family now lived. Without a firm connection to home, I latched on to the part of my identity that felt constant, Vermont, only to find that too was rapidly shifting.

            Vermont, being from here, living here, and going to school here became the prevailing part of my identity. I tied my social capital to Carhartt vests and muck boots. I tried to plug in hokey facts about my pseudo-farm upbringing into conversation to build up my dirt road cred (the Vermont version of street cred). The first thing I ever drove was a tractor. My parents used to raise sheep. We grow a lot of our own food in the summer. All the while, I felt disingenuous. Vermont is all about authenticity and I was trying to sell an inauthentic self.

I became obsessed with them, the “real Vermonters”. I read about them mostly, from Howard Frank Mosher and John Irving. There are fewer and fewer now. Because of nationalized milk prices small family farms have trouble competing with California agro-industry. Most loggers now cut wood for fireplaces and woodstoves. They may never have existed in the way I see them, as noble heroes in my favorite novels. They may have just been people living the only lifestyle available to them and nowadays, where people have more choice, they’re choosing easier and more stable livelihoods. It makes the ones that remain, the ones that still choose the hard way, even more fascinating to me.

I met a few of them, namely my neighbor Russell, but in person they scared me. They provided a foil that made me feel phony. Who was I to call myself a Vermonter next to actual farmers and loggers? Their Vermont accents were strong, and almost unintelligible, making the glottal stop I proudly heard in my own speech seem feeble. I couldn’t claim to be one of them, even though in any other place living there your whole life was enough, here it wasn’t. I felt stranded. I was unable to authentically claim to be a Vermonter, but I wasn’t from anywhere else.

I hoped that this adventure would bring me some clarity on that front. I thought if I engaged in something I so glorified, it might illuminate where I fit in all of it. If I loved “old Vermont” so much and if I really wanted to save it, I needed to try to live it. I’m not entirely sure what I did gain from it. I think it’s a common theme, at this point in a young person’s life, to feel a yearning for a not-so-distant past. As we start out on our new lives, we use our parents’ and grandparents’ lives as a template. It is easier to find one’s place in an event that has already happened, harder to find it in a shifting, nebulous future. I don’t have a past to yearn for, so I yearn for someone else’s.

I’m not disappointed that we don’t smuggle anymore. The actual act of illegally transporting liquor doesn’t interest me much. What I really wanted to connect with were the communities, the lifestyles, and the people that were worth risking everything for. It’s what they were trying to save, not what they were trying to sell when they smuggled that compelled me.

I still carefully lament that the things they were trying to save are slowly fading. Perhaps now though, I lament that fewer people seem to want them in the same way that I do. Fewer people seem to be growing up understanding the value in tradition, community, and making a living from the land. If we as a state let these things slip away, we become just like everywhere else. So I’m going to keep looking for them, the “real Vermonters”, and hope that in the search I discover some of what I admire in them in me.