4 days in Southern Vermont Itinerary

4 days in Southern Vermont Itinerary

Created using Inspirock Southern Vermont trip planner

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Route & dates

4 days in Southern Vermont Itinerary

Start: San Francisco
Fly + Drive:  10​h
1
Brattleboro
— 1 day
Drive:  1​h 15​min
2
Bennington
— 2 nights
Drive + Fly:  10​h
End: San Francisco

1
day
Brattleboro

Brattleboro ©
Brattleboro, originally Brattleborough, is a town in Windham County, Vermont, United States. Start off your visit on the 13th (Sat): brush up on your knowledge of spirits at Saxtons River Distillery, experience rural life at Green Mountain Orchards, relax in the rural setting at Robb Family Farm, then stop by Delectable Mountain Cloth, and finally hunt for treasures at Twice Upon a Time.

For more things to do, other places to visit, reviews, and more tourist information, go to the Brattleboro trip planner .

San Francisco to Brattleboro is an approximately 10-hour flight. You can also drive. The time zone difference moving from Pacific Standard Time to Eastern Standard Time is 3 hours. Traveling from San Francisco in October, things will get slightly colder in Brattleboro: highs are around 62°F and lows about 40°F. Wrap up your sightseeing on the 13th (Sat) early enough to travel to Bennington.

Things to do in Brattleboro

Shopping Breweries & Distilleries

Side Trip

Green Mountain Orchards
Highlights from your plan
Delectable Mountain Cloth ©
Delectable Mountain Cloth
Robb Family Farm ©
Robb Family Farm
Saxtons  Distillery ©
Saxtons Distillery

2
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. Kick off your visit on the 14th (Sun): explore and take pictures at Molly Stark Trail, admire the majestic nature at Woodford State Park, and then explore the different monuments and memorials at New Catholic Cemetery. Keep things going the next day: look for gifts at Hemmings Motor News Filling Station, tour the pleasant surroundings at Dana L. Thompson Memorial Park, and then stop by Fiddlehead at Four Corners.

To see where to stay, more things to do, traveler tips, and other tourist information, refer to the Bennington day trip planning app .

Getting from Brattleboro to Bennington by car takes about 1.5 hours. In October, plan for daily highs up to 62°F, and evening lows to 41°F. Wrap up your sightseeing on the 15th (Mon) to allow time to travel back home.

Things to do in Bennington

Parks Nature Outdoors

Side Trips

Woodford State Park, Dana L. Thompson Memorial Park
Highlights from your plan
Woodford State Park ©
Woodford State Park
New Catholic Cemetery ©
New Catholic Cemetery
Hemmings Motor News Filling Station ©

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