The Itinerary Simplified

DISCOVER

Looking for a stunning road trip this fall? May we suggest six towns in Vermont that will take you from the “Northern Kingdom” to the southern reaches of the Green Mountains. The entire drive is a hair less than 8 hours… not accounting for a few excursions!

Burlington seems to be a great starting point, if you are flying in to Vermont. If you happen to be driving from the south, just pick up in Grafton or Manchester and follow the loop from there.

For those who can take the time, this is a great trip over a week. Depending on your preferences, some towns are going to call you to linger. Others may be satisfied in an afternoon. The itinerary is a bit long for a weekend, so consider shortening it a bit if you just have a couple days, so that you can soak in the beauty. Fall can be busy on the Vermont byways as the magic of this season unfurls, so bring a picnic basket filled with hearty fare and maple sweets and soak in every turn.

Want a few not to miss recommendations?

Visit a sugar house and learn about the art of making maple syrup.
Buy maple syrup to take home!
Enjoy apple picking & cider donuts!
Fall to the temptation to try the donuts as you find them along the way, otherwise, how will you know which is the best?
Don’t rush photos - golden hour takes on a whole new level in the fall.
You will only regret the picture you didn’t take.
Stay at a classic, historic inn and savor the history and ambiance - and hopefully the hearty breakfast.
Don’t rush.

The Itinerary Overview

Want the itinerary with the bells & whistles? Click the button below!

THE DETAILED ITINERARY IS HERE

1. Burlington → Stowe

Miles: 36
Time: ~45 minutes
Summary: Vermont’s lively lakeside city sparkles with farm-to-table restaurants and a creative soul. Stowe dazzles with its mountain backdrop, charming Main Street, and reputation as the epicenter of Vermont’s scenic adventures and outdoor fun.

2. Stowe → Peacham

Miles: 42
Time: ~1 hour
Summary: Stowe’s crisp air and iconic views accompany your journey east to Peacham, one of Vermont’s most picturesque villages—where rolling hills, quaint farms, and white steeples frame every view in classic New England tranquility. Have your camera ready.

fall road with old car in vermont — *Photo cred: @Jacobxrossi Instagram*

3. Peacham → Woodstock

Miles: 64
Time: ~1 hour, 15 minutes
Summary: From Peacham’s rural peace, wind south to Woodstock. This picture-book town brims with history, world-famous covered bridges, and a village green where small-town magic is alive in every window and maple-scented breeze. Prepare to shop, dine, and take in the arts here.

4. Woodstock → Grafton

Miles: 48

Time: ~1 hour, 20 minutes
Summary: Woodstock’s refined charm gives way to Grafton’s timeless beauty, a village framed by historic inns, artisan cheese shops, and iconic countryside—perfect for savoring Vermont’s slow pace and artistic flair.

5. Grafton → Manchester & Dorset

Miles: 34
Time: ~50 minutes
Summary: Follow scenic byways from Grafton into bustling Manchester, known for its boutiques and Lincoln family estate, Hildane. Next-door Dorset, a marble-clad village full of theater, history, and welcoming New England spirit. Shop in the morning, hike in the afternoon. The Green Mountains surround you.

6. Manchester & Dorset → Middlebury

Miles: 61
Time: ~1 hour, 25 minutes
Summary: Leave the Green Mountains for the college town of Middlebury, where stone bridges, artisan shops, and valley views blend to create a vibrant yet peaceful riverfront community.

7. Middlebury → Burlington

Miles: 36
Time: ~45 minutes
Summary: Complete your journey and head straight for the airport or linger amid Burlington’s lakeside energy—a fitting finale of waterside walks, farm-sourced cuisine. .

Any one of these amazing towns is worth a few days to linger - so take you time or pick a few - its a magical road trip!

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