2 days in Freeport & Lenox Itinerary

2 days in Freeport & Lenox Itinerary

Created using Inspirock United States travel route builder

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Route & dates

2 days in Freeport & Lenox Itinerary

Start: Portland
Drive:  30​min
— 1 day
Drive:  4​h 30​min
— 1 night
Drive:  4​h 15​min
End: Portland


Freeport ©
Freeport is a town in Cumberland County, Maine, United States. Kick off your visit on the 15th (Wed): sample the tasty concoctions at Maine Beer Company, immerse yourself in nature at Wolfe's Neck Woods State Park, and then get some fabulous bargains at L.L. Bean Factory Store.

For where to stay, other places to visit, more things to do, and other tourist information, read our Freeport vacation planning site .

Portland to Freeport is an approximately half hour car ride. You can also take a bus; or take a train. May in Freeport sees daily highs of 64°F and lows of 43°F at night. Wrap up your sightseeing on the 15th (Wed) early enough to drive to Lenox.

Things to do in Freeport

Nature Parks Shopping
Highlights from your plan
Wolfe's Neck Woods State Park ©
Wolfe's Neck Woods State Park
Maine Beer Company ©
Maine Beer Company


Lenox ©
Lenox is an affluent town in Berkshire County, Massachusetts, United States. On the 16th (Thu), take in the awesome beauty at Lenox Mountain, admire the masterpieces at Norman Rockwell Museum, and then get engrossed in the history at The Mount, Edith Wharton's Home.

To see photos, traveler tips, reviews, and other tourist information, you can read our Lenox travel route builder tool .

You can drive from Freeport to Lenox in 4.5 hours. Alternatively, you can take a bus; or take a train. In May in Lenox, expect temperatures between 68°F during the day and 45°F at night. Finish up your sightseeing early on the 16th (Thu) so you can go by car back home.

Things to do in Lenox

Museums Nature Parks

Side Trip

Norman Rockwell Museum
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
The Mount, Edith Wharton's Home ©
The Mount, Edith Wharton's Home