8 days in Vermont Itinerary

8 days in Vermont Itinerary

Created using Inspirock Vermont trip maker

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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
— 2 nights
Drive:  1​h 45​min
3
Burlington
— 3 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 and then snap pictures at Silk Road Covered Bridge. Here are some ideas for day two: stop by Manchester Hot Glass, then look for all kinds of wild species at Equinox Preservation Trust, and then take in the dramatic scenery at Lye Brook Falls.

To find reviews, where to stay, photos, and other tourist information, read our Bennington online trip itinerary planner .

Toronto, Canada to Bennington is an approximately 9-hour combination of flight and car. You can also drive. Expect little chillier evenings in Bennington when traveling from Toronto in October, with lows around 5°C. Finish up your sightseeing early on the 6th (Sun) so you can 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
Equinox Preservation Trust ©
Equinox Preservation Trust
Lye Brook Falls ©
Lye Brook Falls

2
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. On the 7th (Mon), stop by Plymouth Artisan Cheese. On the 8th (Tue), you'll have a packed day of sightseeing: take in the views from Taftsville Covered Bridge, then take in the awesome beauty at Mount Tom, and then stroll through Thundering Falls Trail.

To see reviews, where to stay, maps, and tourist information, refer to the Woodstock road trip planner.

You can drive from Bennington to Woodstock in 2 hours. In October in Woodstock, expect temperatures between 19°C during the day and 5°C at night. Finish your sightseeing early on the 8th (Tue) so you can drive to Burlington.

Things to do in Woodstock

Parks Outdoors Nature

Side Trips

Plymouth Artisan Cheese, Thundering Falls Trail
Find places to stay Oct 6 — 8:
Highlights from your plan
Mount Tom ©
Mount Tom
Taftsville Covered Bridge ©
Taftsville Covered Bridge
Plymouth Artisan Cheese ©
Plymouth Artisan Cheese

3
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. You'll discover tucked-away gems like Hope Cemetery and Ethan Allen Homestead. Your cultural itinerary includes sights like Boyden Valley Winery & Spirits and Lake Champlain Maritime Museum. Venture out of the city with trips to Stowe (The Alchemist & Toll Rd) and Craft Beer Cellar (in Waterbury). Next up on the itinerary: do a tasting at Shelburne Vineyard and sample the tasty concoctions at Fiddlehead Brewing Company.

To see more things to do, traveler tips, photos, and tourist information, read Burlington vacation planning tool .

Traveling by car from Woodstock to Burlington takes 2 hours. Alternatively, you can take a bus. In October, daytime highs in Burlington are 19°C, while nighttime lows are 7°C. Finish your sightseeing early on the 11th (Fri) to allow enough time to travel back home.

Things to do in Burlington

Breweries & Distilleries Wineries Outdoors

Side Trips

Stowe, Shelburne, Boyden Valley Winery & Spirits, Lake Champlain Maritime Museum, Hope Cemetery
Find places to stay Oct 8 — 11:
Highlights from your plan
Ethan Allen Homestead ©
Ethan Allen Homestead
Boyden Valley Winery & Spirits ©
Boyden Valley Winery & Spirits
Lake Champlain Maritime Museum ©
Lake Champlain Maritime Museum

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