5 days in Southern Vermont Itinerary

5 days in Southern Vermont Itinerary

Created using Inspirock Southern Vermont visit planner

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Route & dates

5 days in Southern Vermont Itinerary

Start: Boston
Drive:  2​h 30​min
1
Marlboro
— 2 nights
Drive:  1​h 15​min
2
Dorset
— 2 nights
Drive:  3​h 30​min
End: Boston

2
nights
Marlboro

Marlboro ©
Marlboro is a town in Windham County, Vermont, United States. Give yourself a bit of retail therapy at Delectable Mountain Cloth and Twice Upon a Time. Escape the urban bustle at Molly Stark State Park and Woodford State Park. Venture out of the city with trips to Green Mountain Orchards (in Putney) and Molly Stark Trail (in Bennington). And it doesn't end there: relax in the rural setting at Robb Family Farm, sample the fine beverages at Saxtons River Distillery, and learn more about the world around you at Southern Vermont Natural History Museum.

For photos, more things to do, and tourist information, read our Marlboro trip itinerary planner.

Boston to Marlboro is an approximately 2.5-hour car ride. Expect slightly colder evenings in Marlboro when traveling from Boston in September, with lows around 50°F. Cap off your sightseeing on the 18th (Wed) early enough to travel to Dorset.

Things to do in Marlboro

Parks Nature Shopping

Side Trips

Brattleboro, Green Mountain Orchards, Molly Stark Trail, Woodford State Park, Southern Vermont Natural History Museum
Find places to stay Sep 16 — 18:
Highlights from your plan
Molly Stark State Park ©
Molly Stark State Park
Woodford State Park ©
Woodford State Park
Delectable Mountain Cloth ©
Delectable Mountain Cloth

2
nights
Dorset

Dorset ©
Dorset is a town in Bennington County, Vermont, United States. On the 19th (Thu), experience rural life at North Meadow Farm, then tee off at The Golf Club at Equinox, and then contemplate the waterfront views at Battenkill River. On the 20th (Fri), you'll have a packed day of sightseeing: look for gifts at Dorset Union Store, experience rural life at Merck Forest & Farmland Center, then stroll around Dana L. Thompson Memorial Park, and finally explore the activities along Lake Shaftsbury State Park.

For reviews, where to stay, photos, and tourist information, refer to the Dorset day trip tool .

You can drive from Marlboro to Dorset in 1.5 hours. In September, plan for daily highs up to 72°F, and evening lows to 50°F. Finish your sightseeing early on the 20th (Fri) to allow enough time to travel back home.

Things to do in Dorset

Parks Nature Outdoors

Side Trips

Manchester, Battenkill River, Lake Shaftsbury State Park, Merck Forest & Farmland Center
Find places to stay Sep 18 — 20:
Highlights from your plan
Dorset Union Store ©
Dorset Union Store
Lake Shaftsbury State Park ©
Lake Shaftsbury State Park
Dana L. Thompson Memorial Park ©
Dana L. Thompson Memorial Park