Vermont Guides
Walls of rock rising nearly 1,000 feet, boulder caves, and Vermont's most dramatic mountain pass — 45 minutes northeast of Shelburne on Route 108.
Route 108 north of Stowe climbs through a cleft in the mountains that narrows so dramatically it seems impossible that a road goes through at all. Smugglers' Notch — the pass between Mount Mansfield to the south and Sterling Mountain to the north — is a geological accident that became a human convenience: the walls of Conway granite that rise nearly 1,000 feet on either side created a hidden corridor that, for 150 years, was used by people who needed to move things across the Vermont-Quebec border without being noticed.
The smuggling history is real and layered. During Jefferson's 1807 trade embargo, Vermont farmers drove cattle through the notch to sell in Canada. During Prohibition, the same route carried spirits the other direction. The name stuck, and the history has become part of how the place is known — though what most visitors remember is not the history but the geological drama of the walls themselves.
From Heart of the Village Inn in Shelburne, the notch is approximately 45–50 minutes northeast via I-89 North to Exit 10 (Stowe), then Route 100 North through Stowe village and Route 108 up the mountain. The pass is closed in winter — typically late October through May — and the road is narrow enough that large RVs and trailers are prohibited year-round when it is open.
At the highest point of the pass, the road narrows to a single lane in places and the walls close in on both sides. The boulders that have fallen from the cliffs over centuries are enormous — house-sized in some cases — and many have created caves and shelters large enough to walk through. There are signs at the roadside parking area indicating the cave locations; the walk to them is short and requires no hiking experience, though sturdy footwear is recommended over the uneven rock.
The cave known as Smugglers' Cave is the most visited — a narrow passage through a boulder field that, according to local tradition, was actually used to hide contraband. Whether the specific cache was whiskey or cattle is a matter of which account you read.
The best short hike from the notch is to Sterling Pond — a mountain pond that sits at approximately 3,000 feet on the south side of Sterling Mountain. The trailhead is at the parking area at the summit of the pass; the hike is 1.5 miles round trip with a gain of about 1,000 feet. It's steep for a short hike, but the pond is genuine — a dark, cold body of water ringed by conifers, with views back down over the notch and south toward Mount Mansfield's ridge. Most reasonably fit hikers can complete it in 90 minutes to 2 hours round trip.
The Long Trail crosses Route 108 at the notch, running south toward Mount Mansfield and north toward Madonna Peak and the Canadian border. Day-hikers can access the Long Trail in either direction from the pass. The section south toward Mansfield is more traveled; the section north is quieter and gives a sense of the Long Trail's character as a backcountry route rather than a summit day-hike destination.
Even if you don't hike, the drive through Smugglers' Notch on Route 108 is worth making. The road climbs from Stowe on a gradual approach that gives no indication of what's coming — and then the walls appear and the road narrows and the forest closes off the sky except for a strip directly above. It takes about 15 minutes to drive from Stowe village to the summit of the pass, and the pass itself takes another 10 minutes to descend toward Jeffersonville on the north side.
The full loop — Stowe up Route 108 through the notch, then north to Johnson and Route 15 back west to Route 100 South to Waterbury and I-89 — covers some of Vermont's less-visited terrain through the Lamoille River Valley and makes a satisfying day circuit. Jeffersonville has a few independent shops and the Smugglers' Notch Distillery (just east of the village on Route 108), which produces whiskey, vodka, and gin sourced from Vermont grain and is open for tastings.
A dramatic mountain pass on Route 108 between Stowe and Jeffersonville — walls of rock rising nearly 1,000 feet, boulder caves, and a storied history as a smuggling corridor during the trade embargo and Prohibition eras.
Route 108 through the notch is closed in winter — typically late October through May, depending on conditions. Large RVs and trailers are prohibited when open. Confirm current road status before visiting in shoulder seasons.
Sterling Pond — 1.5 miles round trip from the summit parking area, gaining 1,000 feet to a mountain pond with views over the pass. About 90 minutes to 2 hours round trip for most hikers.
Approximately 45–50 minutes via I-89 North to Exit 10, then Route 100 North to Stowe and Route 108 North through the notch.
Heart of the Village Inn is Vermont's only adults-only (21+) B&B in Shelburne Village — 45–50 minutes from Smugglers' Notch. Made-from-scratch breakfast, free on-site parking, and a quiet Vermont village base for the mountains.
Book Now ↗Vermont's highest peak — summit toll road, alpine tundra, and Long Trail ridge walking, 5 minutes south of the notch.
Vermont's third-highest peak and the highest without a ski resort — a classic Green Mountain summit hike, 35 minutes from the inn.
Ben & Jerry's, Cold Hollow Cider Mill, and The Alchemist — 40 minutes from the inn, at the base of the Stowe road.