60 days in Vermont Itinerary

60 days in Vermont Itinerary

Created using Inspirock Vermont visit planner
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Make it your trip
Fly
1
Stowe
— 12 nights
Drive
2
Saint Johnsbury
— 9 nights
Drive
3
Middlebury
— 10 nights
Drive
4
Manchester
— 10 nights
Drive
5
Brattleboro
— 9 nights
Drive
6
Woodstock
— 9 nights
Fly

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Stowe — 12 nights

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.
Get out of town with these interesting Stowe side-trips: Shelburne (Shelburne Farms & Shelburne Museum), Burlington (Burlington Bike Path, Church Street Marketplace, &more) and Montpelier (Bragg Farm Sugar House & Gift Shop, Morse Farm Maple Sugarworks, &more). There's still lots to do: hike along Stowe Recreation Path, take in the dramatic scenery at Moss Glen Falls, ski along the peaceful trails at Trapp Family Lodge Outdoor Center, and cruise along Smugglers Notch State Park.

To see where to stay, more things to do, ratings, and more tourist information, use the Stowe visit planner.

New York City to Stowe is an approximately 2.5-hour flight. You can also drive; or take a train. Plan for little chillier temperatures traveling from New York City in September, with highs in Stowe at 73°F and lows at 48°F. Finish your sightseeing early on the 13th (Mon) so you can drive to Saint Johnsbury.
Parks · Outdoors · Historic Sites · Winter Sports
Side Trips

Saint Johnsbury — 9 nights

St. Get out of town with these interesting Saint Johnsbury side-trips: Groton (Owls Head Trail & Ricker Pond State Park), East Burke (Mount Pisgah & Lake Willoughby) and Newport (MAC Center for the Arts & Lake Memphremagog). And it doesn't end there: walk around Dog Mountain Home of Stephen Huneck Gallery, admire the masterpieces at St. Johnsbury Athenaeum, trek along Lamoille Valley Rail Trail, and get engrossed in the history at Old Stone House Museum.

For maps, photos, traveler tips, and more tourist information, use the Saint Johnsbury trip itinerary maker tool.

Getting from Stowe to Saint Johnsbury by car takes about 1.5 hours. Expect a daytime high around 72°F in September, and nighttime lows around 49°F. Finish up your sightseeing early on the 22nd (Wed) so you can travel to Middlebury.
Parks · Nature · Museums · Trails
Side Trips

Middlebury — 10 nights

Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Change things up with these side-trips from Middlebury: Baird Farm Vermont Maple Syrup (in Chittenden), Allis State Park (in Randolph) and Proctor (Marble Bridge & Vermont Marble Museum). There's much more to do: experience rural life at UVM Morgan Horse Farm, look for gifts at Danforth Pewter, head outdoors with Inn To Inn, and cruise along Lincoln Gap Road.

Take the guesswork out of planning a Middlebury vacation by using our trip itinerary maker.

Drive from Saint Johnsbury to Middlebury in 2.5 hours. In September, daily temperatures in Middlebury can reach 73°F, while at night they dip to 51°F. Finish your sightseeing early on the 2nd (Sat) so you can drive to Manchester.
Nature · Parks · Outdoors · Museums
Side Trips

Manchester — 10 nights

Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Venture out of the city with trips to Woodford State Park (in Woodford), Weston (Mill Museum, Vermont Country Store, &more) and Bennington (The Old First Church, Bennington Battle Monument, &more). There's still lots to do: get engrossed in the history at Hildene, The Lincoln Family Home, relax in the rural setting at North Meadow Farm, tour the pleasant surroundings at Equinox Preservation Trust, and snap pictures at Bridge at the Green.

To find ratings, photos, other places to visit, and more tourist information, go to the Manchester trip itinerary builder.

You can drive from Middlebury to Manchester in 1.5 hours. In October, daily temperatures in Manchester can reach 62°F, while at night they dip to 41°F. Finish your sightseeing early on the 12th (Tue) so you can drive to Brattleboro.
Parks · Museums · Nature · Historic Sites
Side Trips

Brattleboro — 9 nights

Brattleboro, originally Brattleborough, is a town in Windham County, Vermont, United States. Venture out of the city with trips to Rockingham (The Vermont Country Store & Rockingham Meeting House), Molly Stark State Park (in Marlboro) and Wilmington (Harriman Reservoir & The Art of Humor Gallery). And it doesn't end there: brush up on your knowledge of spirits at Saxtons Distillery, take in the views from Creamery Covered Bridge, relax in the rural setting at Retreat Farm, and browse the eclectic array of goods at Brattleboro Farmers' Market.

Find out how to plan Brattleboro trip without stress by asking Inspirock to help create an itinerary.

You can drive from Manchester to Brattleboro in 1.5 hours. October in Brattleboro sees daily highs of 62°F and lows of 40°F at night. Wrap up your sightseeing on the 21st (Thu) to allow time to drive to Woodstock.
Shopping · Museums · Parks · Nature
Side Trips

Woodstock — 9 nights

Woodstock is the shire town of Windsor County, Vermont, United States. Spend the 24th (Sun) exploring nature at Marsh - Billings - Rockefeller National Historical Park. There's much more to do: experience rural life at Sugarbush Farm, contemplate the long history of Billings Farm & Museum, explore the engaging exhibits at Montshire Museum of Science, and take a peaceful walk through Mount Tom.

To see maps, other places to visit, traveler tips, and more tourist information, read Woodstock tour planner.

You can drive from Brattleboro to Woodstock in 1.5 hours. In October, daytime highs in Woodstock are 62°F, while nighttime lows are 40°F. Cap off your sightseeing on the 30th (Sat) early enough to travel back home.
Parks · Historic Sites · Nature · Museums
Side Trips

Vermont travel guide

4.5
Gift & Specialty Shops · Ski Areas · Hiking Trails
The Green Mountain State
Known for its autumn foliage and maple syrup, Vermont is one of the country's smallest states in terms of both population and geographic area. Despite its small size and mostly rural character, the state boasts many picturesque places to visit, including Lake Champlain, one of the nation's largest freshwater bodies. Split in half by the Green Mountains--a popular holiday destination for hiking and skiing--Vermont features a rolling landscape dotted with farms and quaint towns known for their family-run inns, antique shops, and restaurants. Be sure to explore the state's many wild areas while on vacation, but beware of the so-called "mud season," a period of a few weeks when the state's unpaved roads become undrivable due to spring thaw.