5 days in Vermont Itinerary

5 days in Vermont Itinerary

Created using Inspirock Vermont route planner

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Route & dates

5 days in Vermont Itinerary

Start: Boston
Drive:  2​h 15​min
1
Brattleboro
— 1 night
Drive:  1​h 15​min
2
Quechee
— 1 night
Drive:  1​h
3
Montpelier
— 1 night
Drive:  45​min
4
Waitsfield
— 1 night
Drive:  3​h 15​min
End: Boston

1
night
Brattleboro

Brattleboro ©
Brattleboro, originally Brattleborough, is a town in Windham County, Vermont, United States. Kick off your visit on the 17th (Thu): take in the views from Bridge of Flowers, take an in-depth tour of Historic Deerfield, look for gifts at Kringle Candle Company, then snap pictures at Creamery Covered Bridge, and finally browse the eclectic array of goods at Twice Upon a Time. Get ready for a full day of sightseeing on the next day: sample the fine beverages at Saxtons River Distillery, then take in the exciting artwork at The Art of Humor Gallery, then take in the views from Thompson Bridge, and finally get engrossed in the history at Brattleboro Museum and Art Center.

To see more things to do, reviews, where to stay, and more tourist information, read Brattleboro trip site .

Boston to Brattleboro is an approximately 2.5-hour car ride. Traveling from Boston in October, Brattleboro is little chillier at night with lows of 40°F. Wrap up your sightseeing on the 18th (Fri) early enough to drive to Quechee.

Things to do in Brattleboro

Museums Shopping Parks

Side Trips

Historic Deerfield, Bridge of Flowers, Kringle Candle Company, The Art of Humor Gallery, Thompson Bridge
Highlights from your plan
Historic Deerfield ©
Historic Deerfield
The Art of Humor Gallery ©
The Art of Humor Gallery
Twice Upon a Time ©
Twice Upon a Time

1
night
Quechee

Quechee ©
Quechee is a census-designated place and one of five unincorporated villages in the town of Hartford, Windsor County, Vermont, United States. On the 18th (Fri), contemplate the long history of FH Gillingham & Sons General Store.

To find maps, traveler tips, reviews, and more tourist information, read Quechee itinerary maker app .

You can drive from Brattleboro to Quechee in 1.5 hours. In October in Quechee, expect temperatures between 62°F during the day and 40°F at night. Cap off your sightseeing on the 19th (Sat) early enough to go by car to Jericho.

Things to do in Quechee

Historic Sites Shopping

Side Trip

FH Gillingham & Sons General Store
Highlights from your plan
FH Gillingham & Sons General Store ©

1
night
Montpelier

Montpelier ©
Montpelier is the capital city of the U.S. Start off your visit on the 19th (Sat): look for gifts at Cabot Farmers' Store, explore the different monuments and memorials at Hope Cemetery, then make a trip to Bragg Farm Sugar House & Gift Shop, then experience rural life at Morse Farm Maple Sugarworks, and finally pause for some photo ops at Ceres. On your second day here, steep yourself in history at Haverhill-Bath Covered Bridge, then take in the architecture and atmosphere at Blessed Sacrament Church, and then hike along Stowe Recreation Path.

To find maps, reviews, ratings, and other tourist information, you can read our Montpelier trip itinerary planner.

Traveling by car from Quechee to Montpelier takes an hour. In October in Montpelier, expect temperatures between 58°F during the day and 38°F at night. Wrap up your sightseeing on the 20th (Sun) early enough to drive to Waitsfield.

Things to do in Montpelier

Historic Sites Trails Parks

Side Trips

Stowe, Haverhill-Bath Covered Bridge, Cabot Farmers' Store, Hope Cemetery
Highlights from your plan
Hope Cemetery ©
Hope Cemetery
Cabot Farmers' Store ©
Cabot Farmers' Store
Haverhill-Bath Covered Bridge ©
Haverhill-Bath Covered Bridge

1
night
Waitsfield

Waitsfield ©
Waitsfield is a town in Washington County, Vermont, United States. Kick off your visit on the 21st (Mon): make a trip to Northfield Covered Bridges, view the masterpieces at Mad River Glass Gallery, then take in the exciting artwork at Artisans' Gallery, and finally stop by Waitsfield Farmers Market.

To find other places to visit, where to stay, maps, and more tourist information, go to the Waitsfield trip itinerary planner .

Traveling by car from Montpelier to Waitsfield takes an hour. In October, daily temperatures in Waitsfield can reach 58°F, while at night they dip to 38°F. Finish your sightseeing early on the 21st (Mon) to allow enough time to travel back home.

Things to do in Waitsfield

Shopping Museums

Side Trip

Northfield Covered Bridges
Highlights from your plan
Artisans' Gallery ©
Artisans' Gallery
Mad River Glass Gallery ©
Mad River Glass Gallery
Northfield Covered Bridges ©
Northfield Covered Bridges

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