8 days in Vermont Itinerary

8 days in Vermont Itinerary

Created using Inspirock Vermont journey planner

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Route & dates

8 days in Vermont Itinerary

Start: Toronto
Fly + Drive:  8​h 45​min
1
Bennington
— 2 nights
Drive:  1​h 45​min
2
Woodstock
— 3 nights
Drive:  1​h 45​min
3
Burlington
— 2 nights
+2
bus + Fly + ferry:  6​h 30​min
End: Toronto

2
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Start off your visit on the 5th (Sat): take your sightseeing to a higher altitude at Equinox Mountain, then snap pictures at Silk Road Covered Bridge, and then stroll the grounds of The Old First Church. Here are some ideas for day two: stop by Manchester Hot Glass, then identify plant and animal life at Equinox Preservation Trust, and then admire the sheer force of Lye Brook Falls.

For maps, more things to do, traveler tips, and other tourist information, refer to the Bennington trip itinerary website .

Toronto, Canada to Bennington is an approximately 9-hour combination of flight and car. You can also drive. Traveling from Toronto in October, Bennington is a bit cooler at night with lows of 5°C. Cap off your sightseeing on the 6th (Sun) early enough to go by car to Woodstock.

Things to do in Bennington

Parks Nature Wildlife

Side Trips

Manchester, Equinox Mountain
Find places to stay Oct 4 — 6:
Highlights from your plan
Equinox Mountain ©
Equinox Mountain
The Old First Church ©
The Old First Church
Equinox Preservation Trust ©
Equinox Preservation Trust

3
nights
Woodstock

Woodstock
Woodstock is the shire town of Windsor County, Vermont, United States. Take a break from the city and head to Thundering Falls Trail and Ottaquechee River. Get some historical perspective at President Calvin Coolidge State Historic Site and FH Gillingham & Sons General Store. Change things up with a short trip to Buttermilk Falls in Ludlow (about 40 minutes away). The adventure continues: steep yourself in history at Calvin Coolidge Homestead, take a peaceful walk through Mount Tom, and take in the views from Taftsville Covered Bridge.

Make your Woodstock itinerary with Inspirock to find out what to see and where to go.

Drive from Bennington to Woodstock in 2 hours. In October, daytime highs in Woodstock are 19°C, while nighttime lows are 5°C. Finish up your sightseeing early on the 9th (Wed) so you can go by car to Burlington.

Things to do in Woodstock

Parks Nature Historic Sites

Side Trips

Plymouth, Thundering Falls Trail, Buttermilk Falls
Find places to stay Oct 6 — 9:
Highlights from your plan
Mount Tom ©
Mount Tom
FH Gillingham & Sons General Store ©

2
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Start off your visit on the 10th (Thu): explore the galleries of Ethan Allen Homestead, then stroll the grounds of Hope Cemetery, then stop by Craft Beer Cellar, and finally do a tasting at Boyden Valley Winery & Spirits. On the 11th (Fri), you'll have a packed day of sightseeing: explore and take pictures at Toll Rd and then sample the tasty concoctions at The Alchemist.

To find other places to visit, more things to do, reviews, and other tourist information, go to the Burlington trip planner .

Traveling by car from Woodstock to Burlington takes 2 hours. Alternatively, you can take a bus. In October in Burlington, expect temperatures between 19°C during the day and 7°C at night. Finish your sightseeing early on the 11th (Fri) to allow enough time to travel back home.

Things to do in Burlington

Breweries & Distilleries Scenic Drive Outdoors

Side Trips

Stowe, Craft Beer Cellar, Boyden Valley Winery & Spirits, Hope Cemetery
Find places to stay Oct 9 — 11:
Highlights from your plan
Ethan Allen Homestead ©
Ethan Allen Homestead
Hope Cemetery ©
Hope Cemetery
Boyden Valley Winery & Spirits ©
Boyden Valley Winery & Spirits

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