9 days in Vermont Itinerary

9 days in Vermont Itinerary

Created using Inspirock Vermont route maker

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Route & dates

9 days in Vermont Itinerary

Start: Newport News
+2
Taxi + Fly + Bus:  7​h 15​min
1
Manchester
— 1 night
Drive:  1​h 15​min
2
Brattleboro
— 1 night
Drive:  1​h 15​min
3
Woodstock
— 2 nights
Drive:  2​h
4
Greensboro
— 1 night
Drive:  1​h 30​min
5
Shelburne
— 3 nights
Fly + Taxi:  5​h 30​min
End: Newport News

1
night
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. On the 1st (Fri), view the masterpieces at Norman Rockwell Exhibition.

To see where to stay, photos, other places to visit, and more tourist information, go to the Manchester trip itinerary builder site .

Newport News to Manchester is an approximately 7.5-hour combination of taxi, flight, and bus. You can also do a combination of flight and bus; or drive. In May, Manchester is little chillier than Newport News - with highs of 70°F and lows of 45°F. Wrap up your sightseeing on the 2nd (Sat) early enough to drive to Brattleboro.

Things to do in Manchester

Parks Historic Sites Shopping

Side Trips

Weston, Norman Rockwell Exhibition
Highlights from your plan
Lye Brook Falls ©
Lye Brook Falls
Norman Rockwell Exhibition ©
Norman Rockwell Exhibition
Vermont Country Store ©
Vermont Country Store

1
night
Brattleboro

Brattleboro ©
Brattleboro, originally Brattleborough, is a town in Windham County, Vermont, United States. On the 3rd (Sun), hunt for treasures at Twice Upon a Time, sample the fine beverages at Saxtons River Distillery, sample the tasty concoctions at Hermit Thrush Brewery, stop by Hogback Mountain Gift Shop, then get some fabulous bargains at Basketville, and finally don't miss a visit to Creamery Covered Bridge.

To see where to stay, more things to do, photos, and more tourist information, read our Brattleboro day trip planner.

You can drive from Manchester to Brattleboro in 1.5 hours. May in Brattleboro sees daily highs of 69°F and lows of 45°F at night. Wrap up your sightseeing on the 3rd (Sun) to allow time to drive to Woodstock.

Things to do in Brattleboro

Shopping Breweries & Distilleries

Side Trips

Basketville, Hogback Mountain Gift Shop
Highlights from your plan
Basketville ©
Basketville
Hogback Mountain Gift Shop ©
Hogback Mountain Gift Shop
Twice Upon a Time ©
Twice Upon a Time

2
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Kick off your visit on the 4th (Mon): take in the views from Quechee Bridge, brush up on your knowledge of spirits at Vermont Spirits, then look for gifts at Dan & Whit's General Store, then sample the fine beverages at SILO Distillery, and finally take in the views from Cornish-Windsor Bridge. Keep things going the next day: explore the striking landscape at Quechee Gorge, then take in the awesome beauty at Mount Tom, and then indulge your thirst for a good beer at Long Trail Brewing Company.

For reviews, maps, more things to do, and more tourist information, refer to the Woodstock trip itinerary maker site .

Getting from Brattleboro to Woodstock by car takes about 1.5 hours. In May, daily temperatures in Woodstock can reach 70°F, while at night they dip to 45°F. Finish your sightseeing early on the 5th (Tue) so you can travel to Greensboro.

Things to do in Woodstock

Parks Nature Breweries & Distilleries

Side Trips

Quechee, Windsor, Dan & Whit's General Store, Long Trail Brewing Company
Highlights from your plan
Mount Tom ©
Mount Tom
Dan & Whit's General Store ©
Dan & Whit's General Store
Long Trail Brewing Company ©
Long Trail Brewing Company

1
night
Greensboro

Greensboro ©
Greensboro is the southernmost town in Orleans County, Vermont, United States. Start off your visit on the 6th (Wed): immerse yourself in nature at Green River Reservoir State Park, look for gifts at Willey's Store, then indulge your thirst for a good beer at Hill Farmstead Brewery, and finally see the interesting displays at Bread and Puppet Theater.

For reviews, ratings, where to stay, and more tourist information, use the Greensboro route maker app .

Traveling by car from Woodstock to Greensboro takes 2 hours. In May, daily temperatures in Greensboro can reach 66°F, while at night they dip to 44°F. Finish your sightseeing early on the 6th (Wed) so you can travel to Shelburne.

Things to do in Greensboro

Parks Nature Breweries & Distilleries

Side Trips

Green River Reservoir State Park, Hill Farmstead Brewery, Bread and Puppet Theater
Highlights from your plan
Green River Reservoir State Park ©
Green River Reservoir State Park
Hill Farmstead Brewery ©
Hill Farmstead Brewery
Bread and Puppet Theater ©
Bread and Puppet Theater

3
nights
Shelburne

Shelburne ©
Shelburne is a town in southwestern Chittenden County, Vermont, in the United States. You'll explore the less-touristy side of things at Woodchuck Cider House and Shelburne Vineyard. Explore Shelburne's surroundings by going to Middlebury (Lincoln Peak Vineyard, Otter Creek Brewing, & more) and Lake Champlain Maritime Museum (in Vergennes). And it doesn't end there: sample the tasty concoctions at Fiddlehead Brewing Company, stop by The Shelburne Country Store, admire all the interesting features of Dakin Farm, and immerse yourself in nature at Mt. Philo State Park.

For ratings and other tourist information, you can read our Shelburne journey builder .

Traveling by car from Greensboro to Shelburne takes 2 hours. Expect a daytime high around 71°F in May, and nighttime lows around 49°F. Finish your sightseeing early on the 9th (Sat) so you can travel back home.

Things to do in Shelburne

Museums Breweries & Distilleries Wineries

Side Trips

Middlebury, Lake Champlain Maritime Museum, Woodchuck Cider House, Mt. Philo State Park, Dakin Farm
Highlights from your plan
Shelburne Museum ©
Shelburne Museum
Woodchuck Cider House ©
Woodchuck Cider House
Lincoln Peak Vineyard ©
Lincoln Peak Vineyard

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