5 days in New England, Williamsburg & Natural Bridge Itinerary

5 days in New England, Williamsburg & Natural Bridge Itinerary

Created using Inspirock United States sightseeing planner
Make it your trip
Drive
1
Salem
— 1 night
Fly
2
Williamsburg
— 1 night
Drive
3
Natural Bridge
— 1 night
Fly
4
Portland
— 1 night
Drive

S M T W T F S
31
1
2
3
4
5
6

Salem — 1 night

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Kick off your visit on the 2nd (Tue): admire the landmark architecture of Ropes Mansion, contemplate the long history of The Custom House, and then contemplate the long history of Salem Maritime National Historic Site.

For more things to do, maps, ratings, and more tourist information, read our Salem trip itinerary maker tool.

Boston to Salem is an approximately 1-hour car ride. You can also take a train; or take a bus. In August, daytime highs in Salem are 80°F, while nighttime lows are 61°F. Finish your sightseeing early on the 3rd (Wed) to allow enough time to fly to Williamsburg.
Historic Sites

Williamsburg — 1 night

Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
On the 3rd (Wed), steep yourself in history at Governor's Palace, steep yourself in history at George Wythe House, and then get thoroughly spooked out with a ghost and vampire tour.

To see ratings, photos, and tourist information, go to the Williamsburg tour itinerary planner.

You can fly from Salem to Williamsburg in 3 hours. Other options are to drive; or do a combination of train and bus. Traveling from Salem in August, expect Williamsburg to be a bit warmer, temps between 89°F and 70°F. Finish up your sightseeing early on the 4th (Thu) so you can go by car to Natural Bridge.
Historic Sites · Tours

Natural Bridge — 1 night

Natural Bridge is an unincorporated community in Rockbridge County, Virginia, United States. Start off your visit on the 4th (Thu): examine the collection at The Toy Museum at Natural Bridge of Virginia, then stroll through Virginia Safari Park, and then take in the dramatic natural features at Natural Bridge State Park.

To find photos, traveler tips, reviews, and tourist information, use the Natural Bridge online attractions planner.

Getting from Williamsburg to Natural Bridge by car takes about 3.5 hours. Other options: fly; or do a combination of bus and taxi. Traveling from Williamsburg in August, expect Natural Bridge to be little chillier, temps between 71°F and 57°F. Cap off your sightseeing on the 5th (Fri) early enough to catch the flight to Portland.
Parks · Wildlife · Historic Sites · Nature

Portland — 1 night

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Start off your visit on the 5th (Fri): contemplate the long history of Wadsworth-Longfellow House, then stop by Lisa-Marie's Made in Maine, and then steep yourself in history at Fort Gorges.

To find where to stay, reviews, more things to do, and tourist information, read Portland trip itinerary website.

Traveling by flight from Natural Bridge to Portland takes 6.5 hours. Alternatively, you can drive; or do a combination of taxi, train, and bus. Expect a bit warmer weather when traveling from Natural Bridge in August: highs in Portland hover around 79°F, while lows dip to 59°F. You will leave for home on the 6th (Sat).
Historic Sites · Shopping