6 days in Williamstown & Bennington Itinerary

6 days in Williamstown & Bennington Itinerary

Created using Inspirock United States travel route planner

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Route & dates

6 days in Williamstown & Bennington Itinerary

Start: Williamstown
1
Williamstown
— 2 nights
Drive:  30​min
2
Bennington
— 3 nights
Drive:  30​min
End: Williamstown

2
nights
Williamstown

Williamstown ©
Williamstown is a town in Berkshire County, in the northwest corner of Massachusetts, United States. Taconic Trail State Park has been added to your itinerary. Explore the numerous day-trip ideas around Williamstown: The Mount, Edith Wharton's Home (in Lenox), Pittsfield (The Berkshire Carousel & Hancock Shaker Village) and Norman Rockwell Museum (in Stockbridge). Next up on the itinerary: admire the masterpieces at The Clark Art Institute, stop by Where'd You Get That!?, Inc., get lost in a book at Chapin Library of Rare Books and Manuscripts, and take a peaceful walk through Hopkin's Memorial Forest.

Plan my Williamstown trip by asking Inpirock to come up with tips and suggestions.

Use the Route module to find suitable travel options from your home destination to Williamstown. Expect a daytime high around 62°F in October, and nighttime lows around 41°F. Wrap up your sightseeing on the 15th (Tue) to allow time to drive to Bennington.

Things to do in Williamstown

Museums Historic Sites Parks

Side Trips

Pittsfield, The Mount, Edith Wharton's Home, MASS MoCA, Norman Rockwell Museum
Find places to stay Oct 13 — 15:
Highlights from your plan
The Clark Art Institute ©
The Clark Art Institute
Norman Rockwell Museum ©
Norman Rockwell Museum
Williams College Museum of Art ©
Williams College Museum of Art

3
nights
Bennington

Bennington ©
Bennington is a town in Bennington County, Vermont, in the United States. The Old First Church has been added to your itinerary. Kick off your visit on the 16th (Wed): take in nature's colorful creations at Hildene, The Lincoln Family Home, then pause for some photo ops at Bennington Battle Monument, and then stroll the grounds of The Old First Church. Get ready for a full day of sightseeing on the 17th (Thu): learn about winemaking at Adirondack Winery, explore the activities along Lake George, then take your sightseeing to a higher altitude at Prospect Mountain, and finally look for gifts at Bringing You Vermont.

To see where to stay, more things to do, ratings, and more tourist information, read our Bennington tour planner .

Bennington is very close to Williamstown. In October, plan for daily highs up to 62°F, and evening lows to 41°F. Wrap up your sightseeing by early afternoon on the 18th (Fri) to allow enough time to drive back home.

Things to do in Bennington

Parks Historic Sites Nature

Side Trips

Lake George, Saratoga Race Course, Hildene, The Lincoln Family Home
Find places to stay Oct 15 — 18:
Highlights from your plan
Bennington Battle Monument ©
Bennington Battle Monument
Lake George ©
Lake George
The Old First Church ©
The Old First Church