16 days in Vermont Itinerary

16 days in Vermont Itinerary

Created using Inspirock Vermont trip itinerary builder

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Route & dates

16 days in Vermont Itinerary

Start: Kelowna
Fly + Drive:  14​h 15​min
1
Bennington
— 3 nights
Drive:  1​h 45​min
2
Woodstock
— 4 nights
Drive:  1​h 30​min
3
Saint Johnsbury
— 3 nights
Drive:  1​h 45​min
4
Burlington
— 4 nights
bus + Fly:  19​h 30​min
End: Kelowna

3
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Explore the numerous day-trip ideas around Bennington: Creamery Covered Bridge (in Brattleboro), Manchester (Hildene, The Lincoln Family Home, Northshire Bookstore, & more) and Equinox Mountain (in Arlington). Next up on the itinerary: appreciate the history behind Bennington Battle Monument, experience rural life at Mad Tom Orchard, snap pictures at Bridge at the Green, and stroll the grounds of The Old First Church.

To see maps, where to stay, other places to visit, and tourist information, you can read our Bennington trip planning site .

Kelowna, Canada to Bennington is an approximately 14.5-hour combination of flight and car. You can also drive. You'll lose 3 hours traveling from Kelowna to Bennington due to the time zone difference. October in Bennington sees daily highs of 19°C and lows of 5°C at night. Wrap up your sightseeing on the 11th (Fri) early enough to drive to Woodstock.

Things to do in Bennington

Parks Nature Museums

Side Trips

Manchester, Arlington, Putney, Creamery Covered Bridge, Mad Tom Orchard
Highlights from your plan
Hildene, The Lincoln Family Home ©
Bennington Battle Monument ©
Bennington Battle Monument
Bennington Museum ©
Bennington Museum

4
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. You'll find plenty of places to visit near Woodstock: Killington Resort (in Killington) and Vermont Country Store (in Weston). And it doesn't end there: relax in the rural setting at Sugarbush Farm, explore the galleries of Billings Farm & Museum, explore the wealth of natural beauty at Marsh - Billings - Rockefeller National Historical Park, and look for all kinds of wild species at Eshqua Bog Natural Area.

You can plan Woodstock trip in no time by asking Inspirock to help create your itinerary.

Getting from Bennington to Woodstock by car takes about 2 hours. Expect a daytime high around 19°C in October, and nighttime lows around 5°C. Finish up your sightseeing early on the 15th (Tue) so you can go by car to Saint Johnsbury.

Things to do in Woodstock

Parks Historic Sites Nature

Side Trips

Quechee, Killington Resort, Vermont Country Store, President Calvin Coolidge State Historic Site, Eshqua Bog Natural Area
Highlights from your plan
Quechee Gorge ©
Quechee Gorge
Sugarbush Farm ©
Sugarbush Farm
Billings Farm & Museum ©
Billings Farm & Museum

3
nights
Saint Johnsbury

Saint Johnsbury ©
St. Explore Saint Johnsbury's surroundings by going to Stowe (Mount Mansfield State Forest, Stowe Recreation Path, & more) and Montpelier (Vermont State House, Bragg Farm Sugar House & Gift Shop, & more). It doesn't end there: walk around Dog Mountain Home of Stephen Huneck Gallery and admire the striking features of The Dog Chapel.

To find traveler tips, maps, photos, and other tourist information, go to the Saint Johnsbury road trip website .

You can drive from Woodstock to Saint Johnsbury in 1.5 hours. October in Saint Johnsbury sees daily highs of 18°C and lows of 5°C at night. Wrap up your sightseeing on the 18th (Fri) to allow time to drive to Burlington.

Things to do in Saint Johnsbury

Parks Nature Outdoors

Side Trips

Stowe, Montpelier
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Mount Mansfield State Forest ©
Mount Mansfield State Forest

4
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Burlington is known for shopping, trails, parks, zoos & aquariums, and breweries & distilleries. Your plan includes some of its best attractions: hunt for treasures at Church Street Marketplace, contemplate the long history of Shelburne Farms, sample the tasty concoctions at Magic Hat Brewing Company, and gain insight at University of Vermont.

For ratings, maps, and more tourist information, you can read our Burlington road trip planning site .

Getting from Saint Johnsbury to Burlington by car takes about 2 hours. October in Burlington sees daily highs of 19°C and lows of 7°C at night. Finish your sightseeing early on the 22nd (Tue) to allow enough time to travel back home.

Things to do in Burlington

Parks Museums Tours

Side Trips

Shelburne, Magic Hat Brewing Company
Highlights from your plan
Church Street Marketplace ©
Church Street Marketplace
Burlington Bike Path ©
Burlington Bike Path
Waterfront Park ©
Waterfront Park

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