5 Best Scenic Drives in Vermont for September

While October usually gets all the attention for peak foliage, September offers a quieter, less crowded, and equally beautiful experience.

This is the month when you can roll down your windows, enjoy cooler weather, and soak in golden leaves without the heavy tourist rush.

If you’re planning a drive through the Green Mountain State this September, here are the five best scenic routes you absolutely shouldn’t miss.

1. Route 100 Scenic Byway

If there’s one road that defines Vermont in fall, it’s Route 100. Stretching nearly the entire length of the state, this byway takes you past charming small towns, ski resorts preparing for winter, peaceful lakes, and rolling farmland.

The stretch near Killington and Warren is particularly beautiful this time of year. Don’t be surprised if you find yourself pulling over every few miles just to capture the views.

• Best Time in September: Mid to late September for the brightest foliage.
• Driving Distance & Duration: About 216 miles if you do the whole byway; best enjoyed in 2–3 sections (2–4 hours each).
• Nearby Attractions: Moss Glen Falls, Killington ski resort, Warren Falls.
• Food & Drink Stops: Cold Hollow Cider Mill in Waterbury for cider donuts.
• Parking & Accessibility: Plenty of scenic pullouts and village parking areas.
• Map/Route Guidance: Runs north–south through the heart of Vermont; start in Wilmington or Stowe.
• Travel Style Suggestion: Perfect for couples and photographers looking for iconic fall shots.

Pro Tip: Stop at Moss Glen Falls near Granville for a short nature break—it’s one of the easiest waterfalls to see right off the road.

2. Green Mountain Byway

This short but unforgettable drive connects Stowe and Waterbury, two of Vermont’s most loved towns.

Along the way, you’ll see everything that makes Vermont famous: rolling meadows, red barns, covered bridges, and of course, the backdrop of the Green Mountains.

September is an ideal time to explore because Stowe hasn’t yet been overrun with peak foliage crowds.

You can enjoy the road in peace and even take detours for a farm tour or a local maple syrup tasting.

• Best Time in September: Early to mid-September for less traffic, late September for peak colors.
• Driving Distance & Duration: Roughly 11 miles, about 20 minutes without stops—but expect to take 2–3 hours with side trips.
• Nearby Attractions: Stowe Mountain Resort, Waterbury Reservoir, Little River State Park.
• Food & Drink Stops: Ben & Jerry’s factory, local cideries, and maple creemees in Stowe.
• Parking & Accessibility: Ample parking in Stowe and Waterbury, smaller pullouts along the route.
• Map/Route Guidance: Runs between Route 100 in Waterbury and Route 108 in Stowe.
• Travel Style Suggestion: Great for families and foodies who love combining scenery with local flavors.

Pro Tip: End your drive in Waterbury with a scoop of ice cream at Ben & Jerry’s factory—it’s as Vermont as it gets.

3. Route 9 – Molly Stark Byway

Crossing the southern part of the state from Brattleboro to Bennington, the Molly Stark Byway is a scenic east-to-west drive full of rolling hills, historic towns, and classic New England charm.

Bennington’s covered bridges and Brattleboro’s artsy downtown make perfect stopovers.

• Best Time in September: Mid-September for southern Vermont’s early color shift.
• Driving Distance & Duration: Around 48 miles, about 1.5 hours without stops.
• Nearby Attractions: Bennington Battle Monument, covered bridges, Hogback Mountain overlook.
• Food & Drink Stops: Brattleboro’s local cafés, Bennington’s old-fashioned diners.
• Parking & Accessibility: Free parking available in towns and at scenic overlooks.
• Map/Route Guidance: Follows Route 9 between Brattleboro and Bennington.
• Travel Style Suggestion: Ideal for history buffs and couples who enjoy quiet backroads.

Pro Tip: Take a short hike up Hogback Mountain along the way—you’ll get a panoramic view that stretches into three states.

4. Route 108 – Smugglers’ Notch Pass

Winding through dramatic cliffs and narrow mountain passes, Route 108 is one of Vermont’s most thrilling drives.

Known as Smugglers’ Notch, this road has sharp turns, rock walls, and stunning foliage views.

September is a great month to drive here before peak crowds arrive and before the chance of road closures later in fall.

• Best Time in September: Early to mid-September before weekend traffic builds.
• Driving Distance & Duration: About 18 miles between Stowe and Jeffersonville; 30–40 minutes, longer with stops.
• Nearby Attractions: Smugglers’ Notch State Park, Bingham Falls, Stowe Mountain trails.
• Food & Drink Stops: Local cafés in Stowe and Jeffersonville.
• Parking & Accessibility: Limited pullouts—arrive early for trailhead parking.
• Map/Route Guidance: Runs north from Stowe (Route 108) through Smugglers’ Notch to Jeffersonville.
• Travel Style Suggestion: Perfect for adventure seekers and solo travelers craving a dramatic mountain route.

Pro Tip: Go on a weekday if you can—the weekends can get busy with hikers heading to Stowe Mountain trails.

5. Northeast Kingdom Byway

If you want to experience Vermont at its most unspoiled, head north to the Northeast Kingdom.

This byway takes you through quiet countryside, crystal-clear lakes, and forested hills that glow with early autumn colors in September.

Unlike the busier routes, the Northeast Kingdom feels peaceful and remote.

• Best Time in September: Late September for peak northern foliage.
• Driving Distance & Duration: About 51 miles, 1.5–2 hours without stops.
• Nearby Attractions: Lake Willoughby, Burke Mountain, Crystal Lake State Park.
• Food & Drink Stops: Lyndonville diners and local maple syrup stands.
• Parking & Accessibility: Easy parking at lakes and small towns along the route.
• Map/Route Guidance: Runs along Route 114 and Route 5 between St. Johnsbury and Newport.
• Travel Style Suggestion: Best for nature lovers and road trippers looking for off-the-beaten-path Vermont.

Pro Tip: Pack a picnic and stop at Lake Willoughby, often called the “Lucerne of America” for its fjord-like beauty.

Conclusion

September is truly the sweet spot for Vermont road trips. Whether it’s the iconic Route 100, the adventure of Smugglers’ Notch, or the quiet charm of the Northeast Kingdom, these drives show you the very best of Vermont.

Read More: 8 Best Ziplining Adventures in Vermont This September