14 days in Vermont Itinerary

14 days in Vermont Itinerary

Created using Inspirock Vermont holiday maker
©
Make it your trip
Fly
1
Stowe
— 4 nights
Drive
2
Middlebury
— 2 nights
Drive
3
Woodstock
— 4 nights
Drive
4
Bennington
— 3 nights
Fly

S M T W T F S
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29

Stowe — 4 nights

The Ski Capital of the East

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.
Visiting Stowe Recreation Path and Burlington Bike Path will get you outdoors. Step off the beaten path and head to Hope Cemetery and Bingham Falls. Explore the numerous day-trip ideas around Stowe: Burlington (Ethan Allen Homestead & Queen City Brewery) and Boyden Valley Winery & Spirits (in Cambridge). And it doesn't end there: cruise along Toll Rd, immerse yourself in nature at Underhill State Park, sample some tasty brews at a beer tour and tasting, and explore the stunning scenery at Sterling Falls Gorge.

To find traveler tips, ratings, photos, and tourist information, refer to the Stowe road trip planning tool.

Charlotte to Stowe is an approximately 4-hour flight. You can also drive; or take a train. Plan for slightly colder temperatures traveling from Charlotte in October, with highs in Stowe at 18°C and lows at 4°C. Wrap up your sightseeing on the 15th (Sat) early enough to drive to Middlebury.
more
Parks · Breweries & Distilleries · Nature · Outdoors
Side Trips

Middlebury — 2 nights

Middlebury is the shire town (county seat) of Addison County, Vermont, United States. Kick off your visit on the 16th (Sun): see the interesting displays at New England Maple Museum, then examine the collection at Vermont Marble Museum, then experience rural life at Baird Farm Vermont Maple Syrup, and finally take in the views from Hammond Covered Bridge. On your second day here, see the interesting displays at Lake Champlain Maritime Museum, then indulge your thirst for a good beer at Woodchuck Cider House, and then learn about winemaking at Lincoln Peak Vineyard.

For photos, other places to visit, maps, and other tourist information, you can read our Middlebury online attractions planner.

Drive from Stowe to Middlebury in 1.5 hours. In October, daily temperatures in Middlebury can reach 19°C, while at night they dip to 6°C. Cap off your sightseeing on the 17th (Mon) early enough to go by car to Woodstock.
more
Museums · Wineries · Breweries & Distilleries
Side Trips

Woodstock — 4 nights

Woodstock is the shire town of Windsor County, Vermont, United States. Discover out-of-the-way places like President Calvin Coolidge State Historic Site and Thundering Brook Falls Trail. Simon Pearce Mill and American Precision Museum are good opportunities to explore the local culture. The adventure continues: get curious at Montshire Museum of Science, take in the views from Cornish-Windsor Bridge, sample the fine beverages at Vermont Spirits Distilling Co, and get a taste of the local shopping with Fossil Glass.

To find other places to visit, reviews, ratings, and tourist information, read our Woodstock trip builder.

Getting from Middlebury to Woodstock by car takes about 1.5 hours. In October, plan for daily highs up to 19°C, and evening lows to 5°C. Wrap up your sightseeing on the 21st (Fri) early enough to drive to Bennington.
more
Parks · Museums · Historic Sites · Shopping
Side Trips

Bennington — 3 nights

Bennington is a town in Bennington County, Vermont, in the United States. You'll explore the less-touristy side of things at The Old First Church and Silk Road Covered Bridge. Head to Bennington Potters and The Art of Humor Galleryfor plenty of shopping. Change things up with these side-trips from Bennington: Manchester (Hildene, The Lincoln Family Home, Equinox Preservation Trust, &more). There's more to do: cruise along Molly Stark Trail and snap pictures at Bridge at the Green.

To see traveler tips, more things to do, photos, and other tourist information, read our Bennington trip planning tool.

You can drive from Woodstock to Bennington in 2 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 19°C, and evening lows to 5°C. Finish up your sightseeing early on the 24th (Mon) so you can catch the flight back home.
more
Parks · Historic Sites · Shopping · Museums
Side Trips

Vermont travel guide

4.5
Gift & Specialty Shops · Ski Areas · Historic Sites
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.
more