8 days in Vermont Itinerary

8 days in Vermont Itinerary

Created using Inspirock Vermont trip planner

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Route & dates

8 days in Vermont Itinerary

Start: Washington DC
Fly + Drive:  5​h 45​min
1
Bennington
— 1 night
Drive:  1​h
2
Brattleboro
— 2 nights
Drive:  1​h 15​min
3
Woodstock
— 1 night
Drive:  1​h 30​min
4
Stowe
— 3 nights
bus + Fly:  6​h 15​min
End: Washington DC

1
night
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Start off your visit on the 12th (Mon): appreciate the history behind Bennington Battle Monument and then take in the spiritual surroundings of The Old First Church.

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

Washington DC to Bennington is an approximately 6-hour flight. You can also drive. Traveling from Washington DC in August, things will get slightly colder in Bennington: highs are around 79°F and lows about 55°F. Finish your sightseeing early on the 13th (Tue) so you can drive to Brattleboro.

Things to do in Bennington

Museums Historic Sites Parks

Side Trips

Hildene, The Lincoln Family Home, The Clark Art Institute
Highlights from your plan
The Clark Art Institute ©
The Clark Art Institute
Bennington Battle Monument ©
Bennington Battle Monument
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home

2
nights
Brattleboro

Brattleboro, originally Brattleborough, is a town in Windham County, Vermont, United States. Kick off your visit on the 14th (Wed): take in the views from Creamery Covered Bridge, learn about winemaking at Honora Winery & Vineyard, and then whizz through the canopy at some of the top local zipline courses and adventure parks. On your second day here, brush up on your knowledge of spirits at Saxtons River Distillery, contemplate the long history of Historic Deerfield, then take in the views from Bridge of Flowers, and finally take in the dramatic natural features at Glacial Potholes.

To find maps, photos, other places to visit, and more tourist information, use the Brattleboro holiday planning website .

Traveling by car from Bennington to Brattleboro takes an hour. In August, daily temperatures in Brattleboro can reach 79°F, while at night they dip to 56°F. Finish your sightseeing early on the 15th (Thu) to allow enough time to drive to Woodstock.

Things to do in Brattleboro

Outdoors Tours Adventure

Side Trips

Shelburne Falls, Zipline, Honora Winery & Vineyard, Historic Deerfield
Highlights from your plan
Zipline
Bridge of Flowers ©
Bridge of Flowers
Saxtons  Distillery ©
Saxtons Distillery

1
night
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Start off your visit on the 16th (Fri): contemplate the long history of Billings Farm & Museum, then explore and take pictures at Sugarbush Farm, and then take in breathtaking views at Quechee Gorge.

To find other places to visit, traveler tips, more things to do, and more tourist information, read Woodstock tour itinerary builder .

Drive from Brattleboro to Woodstock in 1.5 hours. In August, plan for daily highs up to 81°F, and evening lows to 56°F. Cap off your sightseeing on the 16th (Fri) early enough to go by car to Stowe.

Things to do in Woodstock

Historic Sites Museums Nature

Side Trip

Quechee Gorge
Highlights from your plan
Billings Farm & Museum ©
Billings Farm & Museum
Sugarbush Farm ©
Sugarbush Farm
Quechee Gorge ©
Quechee Gorge

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: Shelburne Museum (in Shelburne) and Burlington (Church Street Marketplace & Burlington Bike Path). Next up on the itinerary: trek along Stowe Recreation Path, take in the awesome beauty at Mount Mansfield State Forest, cruise along Smugglers Notch State Park, and look for gifts at Stowe Mercantile.

Plan a Stowe trip in moments using our itinerary builder.

Traveling by car from Woodstock to Stowe takes 1.5 hours. Alternatively, you can do a combination of bus and train; or take a train. Expect a daytime high around 78°F in August, and nighttime lows around 55°F. Finish your sightseeing early on the 19th (Mon) to allow enough time to travel back home.

Things to do in Stowe

Parks Outdoors Nature

Side Trips

Burlington, Shelburne Museum
Highlights from your plan
Stowe Recreation Path ©
Stowe Recreation Path
Mount Mansfield State Forest ©
Mount Mansfield State Forest
Shelburne Museum ©
Shelburne Museum

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