Vermont has roughly eight thousand roads, and every October they all seem to end up on someone's Instagram. If you want to get beyond the most-traveled routes, this list is where to start. Each of these drives is under two hours, starts within fifteen minutes of Quechee or Woodstock, and offers the kind of scenery that holds up without filters.
1. Cloudland Road (Pomfret)
The single most photographed road in Vermont — and for good reason. A narrow dirt lane running through working farmland with sweeping views of the valley, Cloudland became famous thanks to the Sleepy Hollow Farm that anchors it. It's still spectacular, but please note: the stretch directly in front of the farm is now closed to visitors during peak season. Drive the rest of the road, park respectfully, and let residents live in peace.
Best time: Early morning, first two weeks of October Loop back: Route 12 through Woodstock (about 35 minutes total)
2. The River Road Loop (Quechee → Taftsville → Woodstock)
One of our favorite gentle drives — paved the whole way, perfect for convertibles or family trips. Start at Quechee Gorge, follow the Ottauquechee River east on Route 4, turn onto River Road just before Taftsville, cross the Taftsville Covered Bridge, and roll into Woodstock the back way.
Best time: Late afternoon for golden light Time: 45 minutes including photo stops
3. Route 14 to Sharon
A quieter north-south road that follows the White River. The hardwoods here turn a week or so later than higher elevations, which makes Route 14 a great backup if you arrive after peak has passed in Woodstock.
Best time: Second to third week of October Highlight: The stretch between South Royalton and Tunbridge
4. The Silver Lake Loop (Barnard)
Silver Lake is one of the region's best-kept secrets — a pristine glacial lake ringed by birches and sugar maples. The loop drive takes you through Barnard village, past the Barnard General Store (essential stop, good sandwiches), and around the lake.
Best time: Early October, still morning for reflections Loop pairing: Combine with Cloudland Road for a perfect half-day
5. Route 106 to South Woodstock
If you've only driven Route 4, you're missing Route 106. This south-of-Woodstock road climbs gently through the Green Mountain Horse Association country, past the iconic Kedron Valley Inn, and into rolling high pastureland with long mountain views. It's horse country, and it looks the part.
Best time: Any clear day in October Pair with: Lunch at the Kedron Valley Inn
6. The Covered Bridge Loop
Vermont has more than 100 covered bridges and the Upper Valley has four of the prettiest. Our loop: start at the Middle Bridge in Woodstock, drive Route 12 north to the Lincoln Bridge, continue to Taftsville Covered Bridge, then finish at Quechee Covered Bridge. Short drive, big payoff.
Best time: Mid-October, late morning Time: 90 minutes including stops
7. Route 100 — The One Everyone Talks About
We'd be remiss not to mention it. Route 100 is genuinely one of the great American drives, and the stretch from Killington south to Ludlow is world-class. The trade-off is traffic. If you go:
- Leave by 7:30 AM
- Pack lunch (restaurants fill up)
- Take side roads liberally — Route 100A and River Road are quieter
Best time: Weekdays, first week of October
Practical Tips
- Start early. The best light is between 7 and 10 AM, and you'll avoid the tour buses.
- Dirt roads are the point. A regular sedan handles them fine in dry October weather. Slow down, pull over for oncoming traffic, and wave.
- Respect the farms. Many of the iconic views are on working private land. Stay on public roads, never trespass, and don't block driveways.
- Download offline maps. Cell coverage is patchy once you leave Route 4.
Where to Base Yourself
For access to all seven drives, Quechee and Woodstock are the two best bases. Both are within 15 minutes of every route on this list. Our homes here come with guidebooks, marked paper maps, and a concierge you can text from the car.
The secret to a great foliage trip isn't chasing the reddest tree. It's finding the road where you can pull over, roll down the windows, and hear nothing at all.
