5 days in Western Massachusetts Itinerary

5 days in Western Massachusetts Itinerary

Created using Inspirock Western Massachusetts itinerary maker

©
Make it your trip
Fly to Bradley International Airport, Drive to Pittsfield
1
Pittsfield
— 3 nights
Drive
2
South Deerfield
— 1 night
Drive to Bradley International Airport, Fly to San Diego International Airport

S M T W T F S
4
5
6
7
8
9
10
11
12
13
14
15
16
17

Pittsfield

— 3 nights
Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Explore the numerous day-trip ideas around Pittsfield: Papermill Village Bridge (in North Bennington), Hildene, The Lincoln Family Home (in Manchester) and The Clark Art Institute (in Williamstown). And it doesn't end there: steep yourself in history at Hancock Shaker Village, explore the world behind art at Norman Rockwell Museum, get engrossed in the history at The Mount, Edith Wharton's Home, and take a memorable drive along Concepts of Art Lenox Judaica.

To see photos, maps, traveler tips, and other tourist information, go to the Pittsfield trip itinerary planning website.

San Diego to Pittsfield is an approximately 13-hour combination of flight and car. You can also drive. The time zone difference moving from Pacific Standard Time to Eastern Standard Time is 3 hours. When traveling from San Diego in October, plan for slightly colder days in Pittsfield, with highs around 60°F, while nights are cooler with lows around 40°F. Wrap up your sightseeing on the 10th (Sat) early enough to drive to South Deerfield.

Things to do in Pittsfield

Museums · Historic Sites · Parks · Shopping

Side Trips

South Deerfield

— 1 night
South Deerfield is a census-designated place (CDP) in Deerfield, Franklin County, Massachusetts, United States. Start off your visit on the 11th (Sun): experience rural life at Clarkdale Fruit Farms.

To find ratings, other places to visit, where to stay, and more tourist information, read South Deerfield trip website.

Getting from Pittsfield to South Deerfield by car takes about 1.5 hours. Other options: drive. In October, daily temperatures in South Deerfield can reach 62°F, while at night they dip to 40°F. You will have some time to spend on the 11th (Sun) before leaving for home.
Highlights from your trip