12 days in Vermont Itinerary

12 days in Vermont Itinerary

Created using Inspirock Vermont Trip Planner

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Route & dates

12 days in Vermont Itinerary

Start: Anchorage
+2
Drive + Fly + Bus:  13​h 30​min
1
Manchester
— 3 nights
Drive:  1​h 15​min
2
Killington
— 3 nights
Drive:  2​h
3
Greensboro Bend
— 3 nights
Drive:  1​h 30​min
4
Shelburne
— 1 night
Fly + Drive:  11​h 30​min
End: Anchorage

3
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Visit The Old First Church and Hildene, The Lincoln Family Home for their historical value. Get in touch with nature at Lye Brook Falls and Taylor Farm. You'll find plenty of places to visit near Manchester: Hidden Springs Maple (in Putney), Vermont Country Store (in Weston) and The Art of Humor Gallery (in Wilmington). And it doesn't end there: take in the exciting artwork at Southern Vermont Arts Center, identify plant and animal life at Equinox Preservation Trust, and look for gifts at Orvis.

For other places to visit, maps, ratings, and more tourist information, read Manchester online itinerary creator.

Anchorage to Manchester is an approximately 13.5-hour combination of car, flight, and bus. You can also drive. The time zone difference when traveling from Anchorage to Manchester is 4 hours. Expect somewhat warmer temperatures when traveling from Anchorage in October; daily highs in Manchester reach 60°F and lows reach 41°F. Wrap up your sightseeing on the 30th (Tue) to allow time to travel to Killington.

Things to do in Manchester

Parks Shopping Museums

Side Trips

The Art of Humor Gallery, The Old First Church, Sugar Shack, Hidden Springs Maple, Taylor Farm
Highlights from your plan
Lye Brook Falls ©
Lye Brook Falls
The Old First Church ©
The Old First Church
Equinox Preservation Trust ©
Equinox Preservation Trust

3
nights
Killington

Killington ©
Killington is a town in Rutland County, Vermont, United States. Escape the urban bustle at Mount Tom and Ottaquechee River. You'll explore the less-touristy side of things at Calvin Coolidge Homestead and Vermont Marble Museum and Gift Shop. You'll find plenty of places to visit near Killington: Quechee Gorge Village Vermont Antique Mall (in Quechee) and Woodstock (Sugarbush Farm & Marsh - Billings - Rockefeller National Historical Park). There's more to do: hike along Thundering Falls Trail and sample the tasty concoctions at Long Trail Brewing Company.

To find traveler tips, maps, other places to visit, and tourist information, you can read our Killington trip planner.

Traveling by car from Manchester to Killington takes 1.5 hours. In October, daytime highs in Killington are 57°F, while nighttime lows are 41°F. Finish your sightseeing early on the 2nd (Fri) to allow enough time to travel to Greensboro Bend.

Things to do in Killington

Parks Nature Historic Sites

Side Trips

Woodstock, Vermont Marble Museum, Quechee Gorge Village Vermont Antique Mall, Long Trail Brewing Company, Calvin Coolidge Homestead
Highlights from your plan
Mount Tom ©
Mount Tom
Vermont Marble Museum ©
Vermont Marble Museum

3
nights
Greensboro Bend

Greensboro Bend ©
Start off your visit on the 3rd (Sat): explore the different monuments and memorials at Hope Cemetery, then hike along Stowe Recreation Path, and then stop by Laughing Moon Chocolates. Here are some ideas for day two: examine the collection at Fairbanks Museum & Planetarium, admire the sheer force of Moss Glen Falls, and then snap pictures at Gold Brook Covered Bridge (Emily's Covered Bridge).

For where to stay, other places to visit, ratings, and tourist information, you can read our Greensboro Bend vacation planner.

You can drive from Killington to Greensboro Bend in 2 hours. In November in Greensboro Bend, expect temperatures between 42°F during the day and 28°F at night. Wrap up your sightseeing on the 5th (Mon) early enough to travel to Shelburne.

Things to do in Greensboro Bend

Parks Trails Outdoors

Side Trips

Stowe, Hope Cemetery, Fairbanks Museum and Planetarium
Highlights from your plan
Hope Cemetery ©
Hope Cemetery
Stowe Recreation Path ©
Stowe Recreation Path
Fairbanks Museum and Planetarium ©
Fairbanks Museum and Planetarium

1
night
Shelburne

Shelburne ©
Shelburne is a town in southwestern Chittenden County, Vermont, in the United States. On the 5th (Mon), take an in-depth tour of Ethan Allen Homestead, then enjoy unforgettable views with a balloon tour, and then learn about winemaking at Boyden Valley Winery. Keep things going the next day: take in the spiritual surroundings of Round Church, examine the collection at Shelburne Museum, and then learn about winemaking at Shelburne Vineyard.

For ratings, traveler tips, photos, and tourist information, you can read our Shelburne sightseeing planner.

You can drive from Greensboro Bend to Shelburne in 2 hours. In November, plan for daily highs up to 46°F, and evening lows to 31°F. Finish your sightseeing early on the 6th (Tue) to allow enough time to travel back home.

Things to do in Shelburne

Wineries Museums Historic Sites

Side Trips

Ethan Allen Homestead, Round Church, Boyden Valley Winery & Spirits
Highlights from your plan
Boyden Valley Winery & Spirits ©
Boyden Valley Winery & Spirits
Ethan Allen Homestead ©
Ethan Allen Homestead
Shelburne Museum ©
Shelburne Museum

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