Smugglers Notch Hiking Guide: Vermont's Most Dramatic Mountain Pass
Regional Guides January 29, 2026 9 min read

Smugglers Notch Hiking Guide: Vermont's Most Dramatic Mountain Pass

Smugglers Notch is Vermont's most dramatic mountain pass—a narrow gap between Mount Mansfield and Spruce Peak where 1,000-foot cliffs tower above a road so steep and winding it closes each winter. Named for the smugglers who used it to evade trade embargoes in the early 1800s, the notch today draws hikers to some of Vermont's finest trails.

From the notch parking area, you can access Vermont's highest peak, glacial Sterling Pond, mysterious boulder caves, and cliff-face scrambles—all within a few miles. It's a concentration of hiking opportunities unmatched elsewhere in the state.

Trails from the Notch

Sterling Pond Trail

  • Distance: 2.4 miles round trip
  • Elevation Gain: 1,000 feet
  • Difficulty: Moderate

A steep but short climb to Vermont's highest trout pond—a glacial tarn surrounded by cliffs and forest. The pond reflects the surrounding peaks on calm days and offers excellent swimming (cold!) in summer. Sterling Pond Shelter provides backcountry camping.

Hell Brook Trail to Mount Mansfield

  • Distance: 3.2 miles round trip to the Chin
  • Elevation Gain: 1,800 feet
  • Difficulty: Very Strenuous

The most challenging route to Mansfield's summit, Hell Brook is steep, rough, and utterly relentless. Expect rock scrambling, wooden ladders, and constant upward movement. It's the shortest route to Vermont's highest point but demands experience and fitness.

Long Trail South (Elephant's Head)

  • Distance: 2.0 miles round trip
  • Elevation Gain: 800 feet
  • Difficulty: Moderate

A worthwhile spur leads to Elephant's Head, a cliff-top overlook with spectacular views down into the notch. Less traveled than other options and perfect for an afternoon adventure.

Boulder Caves

Giant boulders tumbled from the cliffs above have created a labyrinth of caves and passages at the base of the notch. These aren't true caves but spaces between massive rocks—some requiring hands-and-knees crawling, others tall enough to walk through.

The caves are unmarked but located near the notch parking area. Look for informal paths leading into the boulder fields. Some highlights:

  • Smuggler's Cave: The largest and most visited
  • Various passages: Explore at your own risk; some are tight

A flashlight is essential. The caves can be wet and cold even in summer. Children love them, but supervision is critical—it's easy to get disoriented among the boulders.

Planning Your Visit

Access

Smugglers Notch Road (Route 108) connects Stowe to Jeffersonville. The parking area at the height of land is where most hikes begin. Note: the road is closed November through May due to extreme winter conditions.

Parking

The notch parking area is small and fills early on summer weekends. Arrive before 8 AM or consider hiking in from Stowe Mountain Resort via the Long Trail.

Best Times

  • Late May through October: Road is open; full trail access
  • Fall foliage: Spectacular but crowded
  • Winter: Road closed; backcountry ski access only

Connecting to Mount Mansfield

Smugglers Notch is a major access point for Vermont's highest peak:

To The Chin (4,393 ft)

Multiple routes ascend from the notch:

  • Hell Brook: Direct and brutal (see above)
  • Long Trail North: Slightly longer, less steep, but still challenging
  • Hell Brook Cutoff: Avoids the worst of Hell Brook while still offering adventure

Loop Options

Experienced hikers can create loops using the various trails, though all involve significant elevation gain and technical terrain. Plan for a full day.

Safety Considerations

  • Cliff danger: Stay on trails—the cliffs are unstable and deadly
  • Rockfall: Be aware of loose rock, especially below the cliffs
  • Weather: Conditions on Mansfield can be severe; check forecasts
  • Navigation: Carry a map; trail junctions can be confusing
  • Cave exploration: Don't enter alone; tell someone your plans

Quick Reference

TrailDistanceGainDifficulty
Sterling Pond2.4 mi1,000 ftModerate
Hell Brook3.2 mi1,800 ftVery Strenuous
Elephant's Head2.0 mi800 ftModerate

Smugglers Notch concentrates Vermont's mountain drama into a single spectacular location. Whether you're scrambling up Hell Brook to Mansfield's summit, swimming in Sterling Pond, or exploring the boulder caves, the notch delivers adventure at every level. Just arrive early—this is one of Vermont's most popular hiking destinations for good reason.

Tags: smugglers notch vermont hiking stowe hiking mountain pass cliff trails

More in Regional Guides