7 days in Vermont Itinerary

7 days in Vermont Itinerary

Created using Inspirock Vermont travel route planner
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Make it your trip
Drive
1
Middlebury
Drive
2
Ripton
Drive
3
Hancock
— 2 nights
Drive
4
Woodstock
— 1 day
Drive
5
Killington
— 1 night
Drive
6
Warren
Drive
7
Waitsfield
— 1 night
Drive
8
Waterbury
Drive
9
Stowe
— 1 night
Drive
10
Waterbury
Drive
11
Shelburne
— 1 night
Drive
12
Burlington
Fly

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Middlebury

Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Start off your visit on the 30th (Fri): indulge your thirst for a good beer at Otter Creek Brewing.

To find maps, other places to visit, photos, and more tourist information, you can read our Middlebury trip planner.

Newcomb to Middlebury is an approximately 2-hour car ride. Traveling from Newcomb in September, expect a bit warmer with lows of 51°F in Middlebury. On the 30th (Fri), wrap the sightseeing up by early afternoon so you can drive to Ripton.
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Breweries & Distilleries
Find places to stay Sep 30 — Oct 1:
Highlights from your trip

Ripton

Ripton is a town in Addison County, Vermont, United States. Kick off your visit on the 30th (Fri): hike along Robert Frost Wayside Trail.

To see reviews, more things to do, where to stay, and tourist information, read Ripton trip itinerary maker.

Ripton is just a short distance from Middlebury. In September in Ripton, expect temperatures between 73°F during the day and 51°F at night. Finish your sightseeing early on the 30th (Fri) so you can drive to Hancock.
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Trails · Parks · Outdoors
Find places to stay Sep 30 — Oct 1:

Hancock — 2 nights

Hancock is a town in Addison County, Vermont, United States. To see reviews, maps, where to stay, and other tourist information, go to the Hancock tour planning website.

Hancock is just a stone's throw from Ripton. In September, daytime highs in Hancock are 73°F, while nighttime lows are 51°F. You'll set off for Woodstock on the 2nd (Sun).
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Outdoors · Parks · Tours · Winter Sports
Find places to stay Sep 30 — Oct 2:

Woodstock — 1 day

Woodstock is the shire town of Windsor County, Vermont, United States. Start off your visit on the 2nd (Sun): relax in the rural setting at Billings Farm & Museum and then experience rural life at Sugarbush Farm.

For other places to visit, ratings, maps, and tourist information, read our Woodstock tour builder tool.

Getting from Hancock to Woodstock by car takes about an hour. In October, plan for daily highs up to 62°F, and evening lows to 40°F. Finish up your sightseeing early on the 2nd (Sun) so you can go by car to Killington.
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Historic Sites · Museums
Find places to stay Oct 2 — 3:

Killington — 1 night

Killington is a town in Rutland County, Vermont, United States. To see other places to visit, maps, where to stay, and more tourist information, use the Killington trip planner.

Killington is just a short distance from Woodstock. In October in Killington, expect temperatures between 60°F during the day and 42°F at night. You'll set off for Warren on the 3rd (Mon).
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Parks · Outdoors · Nature · Shopping
Find places to stay Oct 2 — 3:

Warren

Warren is a town in Washington County, Vermont, United States. Kick off your visit on the 3rd (Mon): stop by The Warren Store.

To find where to stay, maps, reviews, and more tourist information, use the Warren trip itinerary maker website.

You can drive from Killington to Warren in an hour. In October, plan for daily highs up to 61°F, and evening lows to 42°F. On the 3rd (Mon), wrap the sightseeing up by early afternoon so you can drive to Waitsfield.
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Shopping
Find places to stay Oct 3 — 4:
Highlights from your trip

Waitsfield — 1 night

Waitsfield is a town in Washington County, Vermont, United States. Start off your visit on the 3rd (Mon): take a pleasant ride with Vermont Icelandic Horse Farm.

For reviews, more things to do, photos, and tourist information, refer to the Waitsfield online trip maker.

Waitsfield is very close to Warren. Expect a daytime high around 58°F in October, and nighttime lows around 38°F. Wrap up your sightseeing on the 4th (Tue) to allow time to drive to Waterbury.
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Tours · Outdoors
Side Trip
Find places to stay Oct 3 — 4:

Waterbury

Waterbury is a town in Washington County in central Vermont, United States. Kick off your visit on the 4th (Tue): get behind the scenes at Cold Hollow Cider Mill.

For where to stay, ratings, photos, and tourist information, go to the Waterbury journey planner.

Waterbury is just a short distance from Waitsfield. In October in Waterbury, expect temperatures between 58°F during the day and 38°F at night. Wrap up your sightseeing by early afternoon on the 4th (Tue) to allow time for the car ride to Stowe.
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Tours
Side Trip
Find places to stay Oct 4 — 5:
Highlights from your trip

Stowe — 1 night

The Ski Capital of the East

Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
For photos, maps, ratings, and more tourist information, read our Stowe journey builder.

Stowe is very close to Waterbury. In October, daily temperatures in Stowe can reach 60°F, while at night they dip to 39°F. Wrap up your sightseeing on the 5th (Wed) early enough to drive to Waterbury.
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Parks · Outdoors · Nature · Shopping
Find places to stay Oct 4 — 5:

Waterbury

Start off your visit on the 5th (Wed): get behind the scenes at Ben & Jerry's.

To find reviews, traveler tips, where to stay, and more tourist information, read Waterbury tour itinerary builder app.

Waterbury is just a stone's throw from Stowe. Wrap up your sightseeing by early afternoon on the 5th (Wed) to allow enough time to drive to Shelburne.
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Tours
Find places to stay Oct 5 — 6:
Highlights from your trip

Shelburne — 1 night

Shelburne is a town in southwestern Chittenden County, Vermont, in the United States. On the 5th (Wed), contemplate the long history of Shelburne Farms and then stop by The Shelburne Country Store.

To find photos, reviews, and tourist information, go to the Shelburne trip builder tool.

Traveling by car from Waterbury to Shelburne takes an hour. Alternatively, you can take a bus. Traveling from Waterbury in October, expect somewhat warmer with lows of 44°F in Shelburne. Finish up your sightseeing early on the 6th (Thu) so you can go by car to Burlington.
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Historic Sites · Shopping
Find places to stay Oct 5 — 6:

Burlington

Burlington is the most populous city in the U.S. state of Vermont and the seat of Chittenden County. Start off your visit on the 6th (Thu): walk around Waterfront Park and then hunt for treasures at Church Street Marketplace.

To see more things to do, other places to visit, photos, and more tourist information, refer to the Burlington trip planner.

Burlington is just a short distance from Shelburne. In October, daily temperatures in Burlington can reach 62°F, while at night they dip to 44°F. On the 6th (Thu), wrap the sightseeing up by early afternoon so you can fly back home.
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Shopping · Parks
Find places to stay Oct 6 — 7:

Vermont travel guide

4.5
The Green Mountain State
Known for its autumn foliage and maple syrup, Vermont is one of the country's smallest states in terms of both population and geographic area. Despite its small size and mostly rural character, the state boasts many picturesque places to visit, including Lake Champlain, one of the nation's largest freshwater bodies. Split in half by the Green Mountains--a popular holiday destination for hiking and skiing--Vermont features a rolling landscape dotted with farms and quaint towns known for their family-run inns, antique shops, and restaurants. Be sure to explore the state's many wild areas while on vacation, but beware of the so-called "mud season," a period of a few weeks when the state's unpaved roads become undrivable due to spring thaw.
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