15 days in Vermont Itinerary

15 days in Vermont Itinerary

Created using Inspirock Vermont itinerary planner

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Route & dates

15 days in Vermont Itinerary

Start: Portland
Fly + Drive:  11​h 15​min
1
Bennington
— 3 nights
Drive:  1​h 45​min
2
Woodstock
— 4 nights
Drive:  1​h 45​min
3
East Burke
— 2 nights
Drive:  2​h
4
Burlington
— 5 nights
Fly:  9​h 45​min
End: Portland

3
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Eschew the tourist crowds and head to The Old First Church and New Catholic Cemetery. Step out of the city life by going to Equinox Preservation Trust and Equinox Mountain. Get out of town with these interesting Bennington side-trips: Green Mountain Adventure Challenge (in Dover), Manchester (Hildene, The Lincoln Family Home & Lye Brook Falls) and Jamaica State Park (in Jamaica). It doesn't end there: look for gifts at Fiddlehead at Four Corners.

Make your Bennington itinerary with Inspirock to find out what to see and where to go.

Portland to Bennington is an approximately 11.5-hour combination of flight and car. You can also drive. The time zone difference when traveling from Portland to Bennington is 3 hours. Traveling from Portland in September, you can expect nighttime temperatures to be slightly colder in Bennington, with lows of 48°F. Cap off your sightseeing on the 25th (Fri) early enough to go by car to Woodstock.

Things to do in Bennington

Parks Nature Outdoors

Side Trips

Manchester, Green Mountain Adventure Challenge, Equinox Mountain, Jamaica State Park
Highlights from your plan
Equinox Preservation Trust ©
Equinox Preservation Trust
The Old First Church ©
The Old First Church
New Catholic Cemetery ©
New Catholic Cemetery

4
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Visiting Montshire Museum of Science and Mount Tom will get you outdoors. You'll explore the less-touristy side of things at President Calvin Coolidge State Historic Site and FH Gillingham & Sons General Store. You'll find plenty of places to visit near Woodstock: Buttermilk Falls (in Ludlow), Texas Falls Recreation Area (in Hancock) and Robert Frost Wayside Trail (in Ripton). There's still lots to do: contemplate the long history of Calvin Coolidge Homestead, look for all kinds of wild species at Eshqua Bog Natural Area, take in the views from Taftsville Covered Bridge, and hike along Thundering Falls Trail.

For where to stay, maps, photos, and other tourist information, read our Woodstock road trip planning website .

You can drive from Bennington to Woodstock in 2 hours. In September, daily temperatures in Woodstock can reach 75°F, while at night they dip to 50°F. Cap off your sightseeing on the 29th (Tue) early enough to travel to East Burke.

Things to do in Woodstock

Parks Wildlife Historic Sites

Side Trips

Quechee, Plymouth, Montshire Museum of Science, Eshqua Bog Natural Area, Thundering Falls Trail
Highlights from your plan
Montshire Museum of Science ©
Montshire Museum of Science
Mount Tom ©
Mount Tom

2
nights
East Burke

East Burke ©
On the 30th (Wed), get lost in a book at St. Johnsbury Athenaeum, then see the interesting displays at Fairbanks Museum and Planetarium, and then explore the activities along Lake Willoughby. On the 1st (Thu), you'll have a packed day of sightseeing: explore the landscape on two wheels at Newport Bike Path, see the interesting displays at Bread and Puppet Theater, and then sample the tasty concoctions at Hill Farmstead Brewery.

To find other places to visit, traveler tips, and other tourist information, read our East Burke day trip planning site .

You can drive from Woodstock to East Burke in 2 hours. Expect slightly colder weather when traveling from Woodstock in September: highs in East Burke hover around 70°F, while lows dip to 48°F. Wrap up your sightseeing on the 1st (Thu) early enough to drive to Burlington.

Things to do in East Burke

Parks Museums Trails

Side Trips

Saint Johnsbury, Bread and Puppet Theater, Hill Farmstead Brewery, Newport Bike Path
Highlights from your plan
Lake Willoughby ©
Lake Willoughby
Bread and Puppet Theater ©
Bread and Puppet Theater
St. Johnsbury Athenaeum ©
St. Johnsbury Athenaeum

5
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Get outdoors at North Beach Park and Alburg Dunes State Park. Hope Cemetery and Ethan Allen Homestead will appeal to history buffs. Get out of town with these interesting Burlington side-trips: Boyden Valley Winery & Spirits (in Cambridge), St. Anne's Shrine (in Isle La Motte) and Round Church (in Richmond). And it doesn't end there: head outdoors with Bingham Falls, see the interesting displays at Lake Champlain Maritime Museum, learn about winemaking at Shelburne Vineyard, and sample the tasty concoctions at The Alchemist.

To find other places to visit, photos, where to stay, and other tourist information, read our Burlington journey builder tool .

You can drive from East Burke to Burlington in 2 hours. Expect somewhat warmer temperatures when traveling from East Burke in October; daily highs in Burlington reach 62°F and lows reach 44°F. Finish up your sightseeing early on the 6th (Tue) so you can travel back home.

Things to do in Burlington

Outdoors Parks Beaches

Side Trips

Stowe, Shelburne, Hope Cemetery, Missisquoi National Wildlife Refuge, St. Anne's Shrine
Highlights from your plan
Boyden Valley Winery & Spirits ©
Boyden Valley Winery & Spirits
St. Anne's Shrine ©
St. Anne's Shrine
Hope Cemetery ©
Hope Cemetery

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