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Black Diamond Spot 400-Rrechargeable, comfortableCheck price on Amazon →The Great Cliff delivers exactly what its dramatic name promises — a sheer rock face that drops away beneath your feet with nothing but Vermont valley spread out below. At just 0.8 miles to the top, this is one of the steepest, most rewarding short hikes in the Green Mountains.
Don’t let the short distance fool you. This trail climbs 600 feet in less than a mile, which translates to a relentless upward grind that’ll have you questioning your fitness level. The blue-blazed trail follows a section of the famous Long Trail through dense hardwood forest — mostly maple and birch that explode with color in early October.
The footing varies from packed dirt to loose rocks, with a few sections where you’ll need to pick your way carefully over exposed roots and stone slabs. About halfway up, the grade kicks into another gear entirely. You’ll know you’re getting close when the trees start to thin and you catch glimpses of sky ahead.
Just before the cliff, a small sign directs you off the Long Trail to the right. The final approach opens onto the Great Cliff itself — a dramatic limestone ledge that feels much higher than its 2,800-foot elevation suggests. The cliff face drops vertically for what looks like hundreds of feet, offering unobstructed views south across the valley you just drove through. On clear days, you can see multiple ridgelines rolling away toward the horizon like green waves.
This trail punches well above its weight class. The 1.6-mile round trip might look easy on paper, but that sustained 600-foot climb will leave most people breathing hard. The steepness is the real challenge here — your legs will feel it, and there’s no switchbacking to ease the grade. I’d call this a solid moderate hike despite the short distance, mainly because of how unrelenting that climb gets in the final third.
Early morning gets you the best light on the cliff and avoids the modest crowds that show up on weekends. Fall foliage season (late September through early October) is spectacular but expect company. I actually prefer this hike in late spring when the leaves are just emerging — the views are more open, and you’ll have the cliff mostly to yourself. Winter hiking is possible but requires microspikes or crampons for the rocky sections.
The trailhead sits right along Route 140 between Wallingford and East Wallingford — look for a small parking pullout on the north side of the road. There’s space for maybe 6-8 cars, so arrive early on weekends. Cell service is spotty to nonexistent once you’re on the trail. No facilities at the trailhead, but Wallingford has everything you need about 10 minutes away. Bring water — this short climb will make you thirsty, and there’s no reliable source along the trail. The cliff itself has no barriers or railings, so keep kids close and watch your footing near the edge.
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