4 days in Southern Vermont, Killington & Woodstock Itinerary

4 days in Southern Vermont, Killington & Woodstock Itinerary

Created using Inspirock Vermont trip planner
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Make it your trip
Drive
1
Brattleboro
Drive
2
Bennington
Drive
3
Manchester
— 1 night
Drive
4
Killington
— 2 nights
Drive
5
Woodstock
Drive

S M T W T F S
10
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16

Brattleboro

Brattleboro, originally Brattleborough, is a town in Windham County, Vermont, United States. You've now added Creamery Covered Bridge to your itinerary. On the 13th (Wed), snap pictures at Creamery Covered Bridge.

To see reviews, ratings, and other tourist information, use the Brattleboro attractions planner.

Framingham to Brattleboro is an approximately 2-hour car ride. In October in Brattleboro, expect temperatures between 62°F during the day and 40°F at night. On the 13th (Wed), you'll have the morning to explore before heading off to Bennington.
Highlights from your trip

Bennington

Bennington is a town in Bennington County, Vermont, in the United States. Your day by day itinerary now includes Papermill Village Bridge, Burt Henry Covered Bridge and Bennington Battle Monument. Kick off your visit on the 13th (Wed): cruise along Molly Stark Trail, get great views at Bennington Battle Monument, snap pictures at Silk Road Covered Bridge, then snap pictures at Burt Henry Covered Bridge, and finally take in the views from Papermill Village Bridge.

For photos, maps, reviews, and tourist information, you can read our Bennington tour planner.

You can drive from Brattleboro to Bennington in an hour. Expect a daytime high around 62°F in October, and nighttime lows around 41°F. Finish your sightseeing early on the 13th (Wed) to allow enough time to drive to Manchester.
Scenic Drive · Outdoors

Manchester — 1 night

Manchester is a town in, and one of two shire towns (county seats) of, Bennington County, Vermont, United States. Plan my Manchester trip by asking Inspirock to come up with tips and suggestions.

Getting from Bennington to Manchester by car takes about an hour. Other options: take a bus. In October, daily temperatures in Manchester can reach 62°F, while at night they dip to 41°F. Wrap up your sightseeing on the 14th (Thu) early enough to drive to Killington.
Parks · Museums · Historic Sites · Nature
Side Trips

Killington — 2 nights

Killington is a town in Rutland County, Vermont, United States. Your day by day itinerary now includes Quechee Gorge, Texas Falls Recreation Area and Thundering Falls Trail.

To find traveler tips, maps, more things to do, and tourist information, refer to the Killington tour itinerary maker site.

Traveling by car from Manchester to Killington takes 1.5 hours. Expect a daytime high around 60°F in October, and nighttime lows around 42°F. Wrap up your sightseeing by early afternoon on the 16th (Sat) to allow enough time to drive to Woodstock.
Parks · Nature · Wildlife · Trails
Side Trips

Woodstock

Woodstock is the shire town of Windsor County, Vermont, United States. On the 16th (Sat), take your sightseeing to a higher altitude at Mount Tom.

To find out how to plan a trip to Woodstock, use our trip itinerary maker.

Woodstock is just a stone's throw from Killington. Expect a daytime high around 62°F in October, and nighttime lows around 40°F. Wrap up your sightseeing on the 16th (Sat) early enough to travel back home.
Parks · Nature
Highlights from your trip