9 days in Philadelphia, Stockbridge & Boston Itinerary

9 days in Philadelphia, Stockbridge & Boston Itinerary

Created using Inspirock United States trip itinerary planner

Make it your trip
Fly
1
Philadelphia
— 1 night
Drive
2
Stockbridge
— 3 nights
Drive
3
Boston
— 4 nights
Fly

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Philadelphia

— 1 night

The City of Brotherly Love

Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S. democracy, as it was once the meeting place for the country's Founding Fathers.
Kick off your visit on the 17th (Sat): don't miss a visit to Liberty Bell Center, then contemplate the long history of Independence Hall, then pause for some serene contemplation at Christ Church, and finally try your luck at Harrah's Philadelphia. Get ready for a full day of sightseeing on the 18th (Sun): take a stroll through Society Hill, then get engrossed in the history at Eastern State Penitentiary, then explore the world behind art at Philadelphia Museum of Art, and finally wander the streets of Rittenhouse Square.

To see traveler tips, photos, where to stay, and tourist information, read Philadelphia trip builder site.

Los Angeles to Philadelphia is an approximately 7-hour flight. You can also drive; or take a bus. The time zone changes from Pacific Standard Time (PST) to Eastern Standard Time (EST), which is usually a 3 hour difference. Traveling from Los Angeles in July, Philadelphia is somewhat warmer at night with lows of 72°F. Finish your sightseeing early on the 18th (Sun) so you can drive to Stockbridge.

Things to do in Philadelphia

Museums · Historic Sites · Fun & Games · Casinos

Side Trip

Stockbridge

— 3 nights
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Your day by day itinerary now includes National Shrine of the Divine Mercy. Get some historical perspective at Chesterwood Museum and Thomas Cole National Historic Site. Explore Stockbridge's surroundings by going to Hudson (Olana State Historic Site & The Dr. Oliver Bronson House). There's still lots to do: admire the masterpieces at Norman Rockwell Museum, stop by Williams & Sons Country Store, brush up on your knowledge of spirits at Berkshire Mountain Distillers, and admire the natural beauty at Naumkeag.

To see photos, reviews, other places to visit, and more tourist information, you can read our Stockbridge trip itinerary maker website.

You can drive from Philadelphia to Stockbridge in 4 hours. Alternatively, you can do a combination of flight and car; or take a bus. Expect a bit cooler temperatures when traveling from Philadelphia in July; daily highs in Stockbridge reach 79°F and lows reach 59°F. Wrap up your sightseeing on the 21st (Wed) early enough to drive to Boston.

Things to do in Stockbridge

Historic Sites · Museums · Parks · Breweries & Distilleries

Side Trips

Boston

— 4 nights

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Get some historical perspective at Freedom Trail and Louisburg Square. Explore Boston's surroundings by going to Ogunquit (Marginal Way Walkway & Ogunquit Beach). There's lots more to do: wander the streets of North End, walk around Boston Common, appreciate the history behind Bunker Hill Monument, and get a variety of perspectives on a duck tour.

To find reviews, where to stay, and other tourist information, refer to the Boston itinerary planning tool.

Drive from Stockbridge to Boston in 2.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Stockbridge in July, you can expect nighttime temperatures to be somewhat warmer in Boston, with lows of 67°F. Finish your sightseeing early on the 25th (Sun) so you can fly back home.

Things to do in Boston

Historic Sites · Parks · Neighborhoods · Museums

Side Trip