9 days in Vermont Itinerary
9 days in Vermont Itinerary
Created using Inspirock Vermont trip itinerary planner
Route & dates
9 days in Vermont Itinerary
Start: Pittsburgh
+3
Fly + Drive + ferry + Drive:
7h 15min
1
Stowe
— 3 nights
Drive:
1h 30min
2
Woodstock
— 3 nights
Drive:
1h 45min
3
Bennington
— 2 nights
Drive + Fly:
6h 15min
End: Pittsburgh
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3
nights
Stowe
3
nights

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.You'll discover tucked-away gems like Missisquoi National Wildlife Refuge and East Shore Vineyard. Visiting Alburg Dunes State Park and Stowe Recreation Path will get you outdoors. Get out of town with these interesting Stowe side-trips: Burlington (Burlington Bike Path, Burlington City Arts Center, & more), Stone Corral Brewery (in Richmond) and Shelburne Museum (in Shelburne). There's more to do: stop by Stowe Mercantile.
To find traveler tips, more things to do, maps, and more tourist information, go to the Stowe vacation maker app .
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. Expect slightly colder evenings in Stowe when traveling from Pittsburgh in July, with lows around 56°F. Finish up your sightseeing early on the 27th (Sat) so you can go by car to Woodstock.
Things to do in Stowe
Side Trips
Burlington, Alburg Dunes State Park, Shelburne Museum, Stone Corral Brewery, Missisquoi National Wildlife Refuge
Highlights from your plan

Stowe Recreation Path
10:30am, Thu Jul 25

Missisquoi National Wildlife Refuge
11:00am, Sat Jul 27

East Shore Vineyard
4:00pm, Fri Jul 26
3
nights
Woodstock
3
nights

Woodstock is the shire town of Windsor County, Vermont, United States. Escape the urban bustle at Eshqua Bog Natural Area and Rutland Country Club. Explore hidden gems such as New England Maple Museum and McLaughlin Falls. You'll find plenty of places to visit near Woodstock: Killington (Killington Resort & Killington Golf Course). Next up on the itinerary: relax in the rural setting at Sugarbush Farm, look for gifts at Cabot Queechee Store, and explore the stunning scenery at Quechee Gorge.
To find where to stay, photos, and other tourist information, you can read our Woodstock trip website .
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. In July in Woodstock, expect temperatures between 83°F during the day and 59°F at night. Cap off your sightseeing on the 30th (Tue) early enough to go by car to Bennington.
To find where to stay, photos, and other tourist information, you can read our Woodstock trip website .
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. In July in Woodstock, expect temperatures between 83°F during the day and 59°F at night. Cap off your sightseeing on the 30th (Tue) early enough to go by car to Bennington.
Things to do in Woodstock
Side Trips
Killington, New England Maple Museum, Quechee Gorge, Rutland Country Club, Eshqua Bog Natural Area
Highlights from your plan

Killington Resort
10:30am, Sun Jul 28

Eshqua Bog Natural Area
12:00pm, Mon Jul 29

New England Maple Museum
1:00pm, Tue Jul 30
2
nights
Bennington
2
nights

Bennington is a town in Bennington County, Vermont, in the United States. On the 31st (Wed), play a few rounds at Mount Snow Golf Course, then admire the natural beauty at Hildene, The Lincoln Family Home, and then admire the masterpieces at Norman Rockwell Exhibition. Keep things going the next day: stop by Fiddlehead at Four Corners, then learn more about the world around you at Southern Vermont Natural History Museum, then explore the world behind art at Museum of Creative Process, and finally steep yourself in history at Robert Frost Stone House Museum.
To see other places to visit, photos, traveler tips, and tourist information, go to the Bennington online sightseeing planner .
You can drive from Woodstock to Bennington in 2 hours. In July, plan for daily highs up to 81°F, and evening lows to 58°F. Cap off your sightseeing on the 1st (Thu) early enough to travel back home.
To see other places to visit, photos, traveler tips, and tourist information, go to the Bennington online sightseeing planner .
You can drive from Woodstock to Bennington in 2 hours. In July, plan for daily highs up to 81°F, and evening lows to 58°F. Cap off your sightseeing on the 1st (Thu) early enough to travel back home.
Things to do in Bennington
Side Trips
Manchester, Dover, Norman Rockwell Exhibition, Robert Frost Stone House Museum
Highlights from your plan

Hildene, The Lincoln Family Home
3:00pm, Wed Jul 31

Norman Rockwell Exhibition
5:00pm, Wed Jul 31

Southern Vermont Natural History Museum
11:00am, Thu Aug 1
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