10 days in Vermont Itinerary

10 days in Vermont Itinerary

Created using Inspirock Vermont trip itinerary maker

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Route & dates

10 days in Vermont Itinerary

Start: Pittsburgh
+3
Fly + Drive + ferry + Drive:  7​h 15​min
1
Stowe
— 3 nights
Drive:  1​h 30​min
2
Woodstock
— 3 nights
Drive:  1​h 45​min
3
Bennington
— 3 nights
Drive + Fly:  6​h 15​min
End: Pittsburgh

3
nights
Stowe

Stowe ©
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.
Explore the numerous day-trip ideas around Stowe: Waitsfield (Mad River & Waitsfield Farmers Market), Burlington Bike Path (in Burlington) and Dog Mountain Home of Stephen Huneck Gallery (in Saint Johnsbury). There's lots more to do: trek along Stowe Recreation Path, experience rural life at Hacketts Orchard, contemplate the waterfront views at Mad River, and brush up on your knowledge of spirits at Green Mountain Distillers.

To see maps, photos, other places to visit, and tourist information, you can read our Stowe trip itinerary maker website .

Pittsburgh to Stowe is an approximately 7.5-hour combination of flight, ferry, and car. You can also do a combination of flight and bus; or drive. Plan for little chillier nights when traveling from Pittsburgh in July since evenings lows in Stowe dip to 56°F. Cap off your sightseeing on the 29th (Mon) early enough to go by car to Woodstock.

Things to do in Stowe

Parks Outdoors Nature

Side Trips

Waitsfield, South Hero, Green Mountain Distillers, Burlington Bike Path, 1st Republic Brewing Company
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Burlington Bike Path ©
Burlington Bike Path

3
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. You'll find plenty of places to visit near Woodstock: Baird Farm Vermont Maple Syrup (in Chittenden), Brandon (Inn to Inn & Maple View Farm Alpacas) and Texas Falls (in Hancock). There's lots more to do: get curious at Montshire Museum of Science, steep yourself in history at FH Gillingham & Sons General Store, go for a walk through Rutland murals, and witness the site of a historic battle at Hubbardton Battlefield.

Quickly create a custom-made itinerary for Woodstock using our trip planner.

Traveling by car from Stowe to Woodstock takes 1.5 hours. Alternatively, you can do a combination of train and bus; or take a train. Expect a daytime high around 83°F in July, and nighttime lows around 59°F. Finish your sightseeing early on the 1st (Thu) so you can drive to Bennington.

Things to do in Woodstock

Parks Outdoors Historic Sites

Side Trips

Brandon, Rutland, Hubbardton Battlefield, Calvin Coolidge Homestead, Bucklin Trail
Highlights from your plan
Montshire Museum of Science ©
Montshire Museum of Science
FH Gillingham & Sons General Store ©
FH Gillingham & Sons General Store
Maple View Farm Alpacas ©
Maple View Farm Alpacas

3
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Change things up with these side-trips from Bennington: Green Mountain Adventure Challenge (in Dover), Mad Tom Orchard (in East Dorset) and Manchester (North Meadow Farm, Earth Sky Time Community Farm, & more). There's much more to do: stroll the grounds of New Catholic Cemetery, immerse yourself in nature at Lake Shaftsbury State Park, snap pictures at Bridge at the Green, and look for gifts at Bringing You Vermont.

To find more things to do, ratings, photos, and tourist information, read Bennington day trip planning tool .

Getting from Woodstock to Bennington by car takes about 2 hours. August in Bennington sees daily highs of 79°F and lows of 55°F at night. Finish your sightseeing early on the 4th (Sun) to allow enough time to travel back home.

Things to do in Bennington

Parks Nature Outdoors

Side Trips

Manchester, Lake Shaftsbury State Park, Bridge at the Green, Mad Tom Orchard, Green Mountain Adventure Challenge
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
New Catholic Cemetery ©
New Catholic Cemetery
Papermill Village Bridge ©
Papermill Village Bridge

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