Tucked between the towering cliffs of Mount Mansfield and Spruce Peak lies one of Vermont’s most breathtaking drives and most legendary mountain passes: Smugglers’ Notch. Today, it’s known for jaw-dropping foliage, rugged hiking trails, and world-class skiing. But for those who pause long enough to look beyond the scenic views, the Notch has a far more rebellious past.
For over two centuries, Smugglers’ Notch has lived up to its name, offering refuge to bootleggers, smugglers, and secretive travelers who knew exactly how to navigate its shadowy caves and narrow paths. From clandestine trade with Canada during Jefferson’s embargo to liquor runs during Prohibition, this natural corridor has hidden more than just wildlife.
I’ve always seen the Notch as more than a pretty place. Its story is one of resistance, survival, and ingenuity. So let’s take a trip back in time and uncover the secrets that shaped Smugglers’ Notch.

What Makes Smugglers’ Notch So Perfect for Secrets?
Before we dive into the smuggling tales, it helps to understand why this mountain pass was such a magnet for outlaws and traders.
Smugglers’ Notch is a narrow passage in Lamoille County, just south of Jeffersonville and north of Stowe. It carves through Vermont’s highest peaks, with sheer rock walls that close in tightly around the road. Dense forests blanket the sides, and natural caves dot the landscape.
In the early 1800s, there was no paved road here. What existed was little more than a rugged path. No matter the time period, Smugglers’ Notch has always been:
- Hard to access
- Easy to hide in
- Difficult to patrol
For those looking to move people or goods in secret, it offered the perfect setting.
Trading in Defiance: Smuggling During the Embargo Act
Our first stop on the timeline takes us to the early 1800s. President Thomas Jefferson passed the Embargo Act of 1807, effectively banning American trade with foreign nations. The goal was to punish Britain and France during the Napoleonic Wars. The result, however, was economic disaster for Vermont.
Vermonters were used to doing business with their Canadian neighbors. Suddenly, that relationship was cut off by federal law. But Vermonters are nothing if not resourceful. Instead of sitting back, many turned to the Notch.
Goods like:
- Livestock
- Timber
- Furs
- Whiskey
- Canadian products like sugar and tea
were packed on mule trains and slipped across the Canadian border under cover of darkness. The narrow trails through Smugglers’ Notch became a lifeline for the local economy.
Many smugglers knew the caves by heart. They’d stash goods in the rock formations while waiting for the perfect moment to move them further south. Federal agents tried to crack down, but Vermont’s rough terrain and locals’ silence kept the trade alive.
The Whisper of Freedom: Escaped Slaves and the Underground Railroad
While less documented than other chapters, some local legends and oral histories suggest that Smugglers’ Notch may have served as a route for escaped slaves traveling north to freedom.
Vermont abolished slavery in its 1777 constitution and was a stronghold of abolitionist sentiment. The geography of the state provided natural corridors for those making the journey to Canada. While most documented Underground Railroad activity in Vermont happened farther south and west, the remote and hard-to-monitor nature of the Notch raises the possibility that it offered a secondary escape route.
Freedom seekers would have found protection in the same caves used by smugglers. Locals sympathetic to their cause may have passed along food, clothing, or directions. Whether used frequently or occasionally, this part of the Notch’s story speaks to Vermont’s long-standing role in resisting oppression.
Booze, Bootleggers, and the Prohibition Era
Fast forward to the 1920s, and Smugglers’ Notch earns its name all over again.
Prohibition swept across the United States from 1920 to 1933, outlawing the production, importation, and sale of alcohol. Canada, however, had no such ban. So naturally, Vermonters saw opportunity.
Liquor was purchased across the border and funneled through mountain passes like the Notch. The caves that once held furs or livestock now became storage units for Canadian whiskey. Bootleggers moved by foot, mule, or sleigh, depending on the season.
Here’s what made the Notch ideal during Prohibition:
- Limited access roads meant fewer law enforcement patrols
- Local support from farmers and business owners
- Countless hiding places in boulders, caves, and forests

Some stories tell of sleds with false bottoms, filled with booze and hay. Others mention tunnel systems beneath barns and taverns. One particularly popular tale describes a “phantom wagon” that would appear on moonlit nights, its driver cloaked and silent as he guided a load of barrels into the trees.
Whether these stories are exaggerated or not, one thing is clear: the liquor flowed, and the Notch kept its secrets.
Caves, Tunnels, and Tales Too Good to Be True
Smugglers’ Notch is full of caves and crevices, many of which have names like Elephant’s Head and Bear’s Den. Some are accessible from trails. Others are harder to find unless you know exactly where to look.
Over the decades, these natural features have attracted more than hikers. According to local lore, they’ve been used to:
- Store contraband
- Hide fugitives
- Conduct secret meetings
- Escape from pursuing agents
Some believe there are still hidden stashes buried deep in the rock. Others speak of ghosts that haunt the Notch, especially after nightfall. These stories may not always be backed by documents, but they’ve become part of the culture surrounding the area.
I believe legends often grow from seeds of truth. The terrain absolutely could support this kind of activity. Whether a particular cave held whiskey or not, the setting certainly lends itself to mystery.
The Law vs. the Landscape
So where were the authorities during all this?
The answer lies in a mix of geography, logistics, and quiet resistance. In the 1800s and early 1900s, law enforcement had few resources to spare for the mountain wilderness. There were no drones, no GPS, and few roads. A determined smuggler on foot had the upper hand.
Even when patrols were attempted, local residents rarely cooperated. Why would they? In many cases, these activities supported the local economy. Entire communities were built on trust and silence.
Federal agents often faced obstacles like:
- Locals tipping off smugglers
- Winter storms making trails impassable
- Multiple routes in and out of the Notch
- Hidden storage spots impossible to search fully
Some efforts were made, especially during Prohibition, but most ended in frustration. The truth is, the Notch won more battles than it lost when it came to secrecy.
From Smuggling Trails to Hiking Trails
By the mid-1900s, the need for secrecy faded, and the push for conservation and recreation began. The Civilian Conservation Corps (CCC), part of Franklin D. Roosevelt’s New Deal programs in the 1930s, helped transform parts of Smugglers’ Notch into trails and public lands.
What was once a smuggler’s paradise became:
- A state park
- A ski resort
- A scenic drive popular during foliage season
Today, the caves and narrow cliffs that once hid bootleggers now challenge rock climbers and delight curious hikers. The Notch Road (Route 108) is open seasonally to traffic, winding its way through some of the most dramatic mountain scenery in New England.
And if you know where to look, you’ll still find plaques and markers nodding to the history beneath your feet.
Why This History Matters
It would be easy to overlook the Notch’s rebellious past in favor of its natural beauty. But doing so would miss the deeper meaning of this place.
Smugglers’ Notch represents:
- Vermont’s independent spirit
- Resistance to federal overreach
- Creative survival in hard times
- Quiet defiance rooted in community
Whether it was livestock during Jefferson’s embargo, whiskey during Prohibition, or people fleeing enslavement, the Notch played a role in protecting those willing to take a risk.
Even today, locals take pride in that heritage. It’s why the ski resort isn’t just called “Notch Mountain” or “Mansfield Peaks.” The name “Smugglers’ Notch” keeps the stories alive.
Visiting the Notch with History in Mind
If you’re planning a trip to Smugglers’ Notch, consider exploring it through the lens of its past.
Here are a few tips for historical-minded visitors:
- Stop at the pull-offs along Route 108 to see the cliffs and boulders up close
- Hike the Sterling Pond Trail and imagine how smugglers might have traveled through similar terrain

Even if you don’t find a hidden whiskey barrel tucked in a cave, you’ll gain a much richer appreciation for what this mountain pass has witnessed.
Final Thoughts: A Notch With More Than Just Scenic Views
The next time you drive the winding road between Jeffersonville and Stowe, take a moment to picture what came before. Picture mule trains slipping through the trees. Picture bootleggers navigating the cliffs by lantern light. Picture freedom seekers finding a path north under the cover of night.
Smugglers’ Notch is more than a beautiful mountain pass. It’s a living story about Vermont’s resistance, resourcefulness, and refusal to be tamed.
And those secrets? Some of them might still be hiding in the rocks, just waiting to be uncovered.












