35 days in Vermont Itinerary

35 days in Vermont Itinerary

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Route & dates

35 days in Vermont Itinerary

Start: Montreal, Quebec
Drive:  2​h
1
Burlington
— 9 nights
Drive:  1​h
2
Middlebury
— 4 nights
Drive:  1​h 30​min
3
Manchester
— 7 nights
Drive:  1​h 30​min
4
Woodstock
— 9 nights
Drive:  2​h
5
Greensboro Bend
— 4 nights
Drive + Fly:  14​h
End: Montreal, Quebec

9
nights
Burlington

Burlington ©
Burlington is the most populous city in the U.S. Get in touch with nature at Stowe Recreation Path and Mount Mansfield State Forest. Give yourself a bit of retail therapy at Burlington Farmers' Market and Shelburne Country Store. Get out of town with these interesting Burlington side-trips: The Cabot Annex Store (in Waterbury Center), Charlotte (Charlotte Village Winery & Mt. Philo State Park), Stowe (Laughing Moon Chocolates, AJ's Ski & Sports, & more), Jeffersonville (Zipline & Smugglers' Notch Distillery), Vermont Liberty Tea Co (in Waterbury) and Boyden Valley Winery (in Cambridge). And it doesn't end there: kick back and relax at North Beach Park, tour the pleasant surroundings at Burlington Bike Path, learn about winemaking at Beverage Warehouse, and make a trip to Church Street Marketplace.

For ratings, where to stay, reviews, and tourist information, read our Burlington holiday planner.

Use the Route module to find suitable travel options from Laval, Canada to Burlington. Expect a daytime high around 17°C in October, and nighttime lows around 5°C. Cap off your sightseeing on the 16th (Sun) early enough to travel to Middlebury.

Things to do in Burlington

Parks Outdoors Nature

Side Trips

Stowe, Shelburne, Charlotte, South Hero, Beverage Warehouse
Highlights from your plan
Burlington Bike Path ©
Burlington Bike Path
Stowe Recreation Path ©
Stowe Recreation Path
Church Street Marketplace ©
Church Street Marketplace

4
nights
Middlebury

Middlebury ©
Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Get in touch with nature at Mad River and Robert Frost Wayside Trail. You'll find plenty of places to visit near Middlebury: Brandon (Inn to Inn & Brandon Music), Warren Falls (in Warren), Dakin Farm (in Ferrisburg), Lake Champlain Maritime Museum (in Vergennes) and Skinner Barn (in Waitsfield). The adventure continues: do a tasting at Lincoln Peak Vineyard, sample the tasty concoctions at Woodchuck Cider House, relax in the rural setting at UVM Morgan Horse Farm, and stop by Danforth Pewter Workshop & Store.

To find ratings, other places to visit, reviews, and more tourist information, you can read our Middlebury trip generator.

Use the Route module to find suitable travel options from Burlington to Middlebury. In October, daily temperatures in Middlebury can reach 18°C, while at night they dip to 7°C. Wrap up your sightseeing on the 20th (Thu) early enough to travel to Manchester.

Things to do in Middlebury

Parks Outdoors Nature

Side Trips

Brandon, Waitsfield, Warren Falls, Dakin Farm, Woodchuck Cider House
Highlights from your plan
Mad River ©
Mad River
Warren Falls ©
Warren Falls
Woodchuck Cider House ©
Woodchuck Cider House

7
nights
Manchester

Manchester ©
Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Head to Vermont Country Store and Hidden Springs Maplefor some retail therapy. Take a break from the city and head to Jamaica State Park and Woodford State Park. Change things up with these side-trips from Manchester: The Vermont Country Store Rockingham (in Rockingham), DaVallia Art & Accents (in Chester), Brattleboro (Delectable Mountain Cloth, Grafton Village Cheese Company Brattleboro, & more), Bennington (The Apple Barn and Country Bake Shop, Fiddlehead At Four Corners, & more), Molly Stark State Park (in Marlboro) and Honora Winery & Vineyard (in Jacksonville). The adventure continues: stop by Northshire Bookstore, play a few rounds at The Golf Club at Equinox, look for all kinds of wild species at Equinox Preservation Trust, and admire the natural beauty at Hildene, The Lincoln Family Home.

To see ratings, more things to do, photos, and tourist information, read our Manchester sightseeing planner.

Explore your travel options from Middlebury to Manchester with the Route module. In October, daytime highs in Manchester are 18°C, while nighttime lows are 5°C. Cap off your sightseeing on the 27th (Thu) early enough to travel to Woodstock.

Things to do in Manchester

Parks Shopping Nature

Side Trips

Bennington, Brattleboro, Arlington, Hidden Springs Maple, Molly Stark State Park
Highlights from your plan
Hildene, The Lincoln Family Home ©
Hildene, The Lincoln Family Home
Vermont Country Store ©
Vermont Country Store
Vermont Country Store ©
Vermont Country Store

9
nights
Woodstock

Woodstock ©
Woodstock is the shire town of Windsor County, Vermont, United States. Step out of the city life by going to Marsh - Billings - Rockefeller National Historical Park and Quechee Gorge. Head to Beyond Obsession and Green Mountain Sugar Housefor some retail therapy. Get out of town with these interesting Woodstock side-trips: Weirs Beach (Weirs Beach & Kellerhaus), Holderness (Squam Lakes Natural Science Center & West Rattlesnake Mountain), Innisfree Bookshop (in Meredith), Green Mountain National Golf Course (in Killington), White Mountains National Forest (in Laconia), Tanger Outlet Center Tilton (in Tilton) and Spas & Wellness (in Rutland). There's lots more to do: relax in the rural setting at Sugarbush Farm, look for gifts at Barnard General Store, indulge your thirst for a good beer at Long Trail Brewing Company, and delve into the lush surroundings at Mount Tom.

To see traveler tips, more things to do, where to stay, and more tourist information, use the Woodstock vacation builder.

Explore your travel options from Manchester to Woodstock with the Route module. In October in Woodstock, expect temperatures between 18°C during the day and 5°C at night. Wrap up your sightseeing on the 5th (Sat) to allow time to travel to Greensboro Bend.

Things to do in Woodstock

Parks Nature Shopping

Side Trips

Norwich, Quechee, Holderness, Green Mountain National Golf Course, Green Mountain Sugar House
Highlights from your plan
Quechee Gorge ©
Quechee Gorge
West Rattlesnake Mountain ©
West Rattlesnake Mountain

4
nights
Greensboro Bend

Greensboro Bend ©
Do your shopping at Chutters and Willey's Store. Escape the urban bustle at Flume Gorge and Echo Lake Beach. Get out of town with these interesting Greensboro Bend side-trips: Saint Johnsbury (Dog Mountain & St. Johnsbury Athenaeum), Harman's Cheese & Country Store (in Sugar Hill), The Brick Store (in Bath), Fresh Tracks Farm Vineyard & Winery (in Berlin), Franconia Notch State Park (in Franconia) and Montpelier (Morse Farm Maple Sugarworks, Vermont State House, & more).

To see other places to visit, traveler tips, ratings, and tourist information, read Greensboro Bend trip itinerary maker.

Use the Route module to find suitable travel options from Woodstock to Greensboro Bend. Traveling from Woodstock in November, expect nights in Greensboro Bend to be about the same, around -2°C, while days are a bit cooler, around 6°C. Wrap up your sightseeing on the 9th (Wed) to allow time to travel back home.

Things to do in Greensboro Bend

Parks Nature Shopping

Side Trips

Montpelier, Franconia, Saint Johnsbury, Willey's Store, The Brick Store
Highlights from your plan
Flume Gorge ©
Flume Gorge
Franconia Notch State Park ©
Franconia Notch State Park
Chutters ©
Chutters

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