5 days in New England, Williamsburg & Natural Bridge Itinerary

5 days in New England, Williamsburg & Natural Bridge Itinerary

Created using Inspirock United States trip planner
Make it your trip
— 1 night
— 1 night
Natural Bridge
— 1 night
— 1 night


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.
On the 3rd (Mon), admire the landmark architecture of Ropes Mansion, then contemplate the long history of The Custom House, and then contemplate the long history of Salem Maritime National Historic Site.

For where to stay, reviews, and tourist information, use the Salem trip site.

Boston to Salem is an approximately 1-hour car ride. You can also take a train; or take a bus. Traveling from Boston in October, plan for slightly colder nights in Salem, with lows around 45°F. Cap off your sightseeing on the 4th (Tue) early enough to catch the flight 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 4th (Tue), contemplate the long history of Governor's Palace, contemplate the long history of George Wythe House, and then get thoroughly spooked out with a ghost and vampire tour.

To see other places to visit and tourist information, read our Williamsburg journey maker site.

Fly from Salem to Williamsburg in 3 hours. Alternatively, you can drive; or do a combination of train and bus. Prepare for somewhat warmer weather when traveling from Salem in October: high temperatures in Williamsburg hover around 75°F and lows are around 55°F. Cap off your sightseeing on the 5th (Wed) early enough to 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 5th (Wed): examine the collection at The Toy Museum at Natural Bridge of Virginia, stroll through Virginia Safari Park, and then take in the dramatic natural features at Natural Bridge State Park.

To find out how to plan a trip to Natural Bridge, use our trip itinerary maker.

Traveling by car from Williamsburg to Natural Bridge takes 3.5 hours. Alternatively, you can fly; or do a combination of bus and taxi. Expect slightly colder temperatures when traveling from Williamsburg in October; daily highs in Natural Bridge reach 59°F and lows reach 45°F. Wrap up your sightseeing on the 6th (Thu) to allow time to fly 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 6th (Thu): steep yourself in history at Wadsworth-Longfellow House, look for gifts at Lisa-Marie's Made in Maine, and then steep yourself in history at Fort Gorges.

To see traveler tips, reviews, where to stay, and tourist information, use the Portland road trip website.

Fly from Natural Bridge to Portland in 6.5 hours. Alternatively, you can drive; or do a combination of taxi, train, and bus. In October, plan for daily highs up to 62°F, and evening lows to 43°F. You will leave for home on the 7th (Fri).
Historic Sites · Shopping

Massachusetts travel guide

History Museums · Art Museums · Nightlife
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.

Virginia travel guide

History Museums · Wineries & Vineyards · Historic Sites
Old Dominion
The home of the first permanent English colony in the New World, Virginia is a prime holiday destination for those looking to immerse themselves in American heritage. Proud of its colorful history, distinct culture, and southern drawl, Virginians see their state as the place where the imaginary line between the north and the south is drawn. With scenic beauties as diverse as its people, Virginia is a land of rolling hills, rugged mountains, lush valleys, dense forests, and secluded beaches along picturesque bays. Bordered on the east by the Atlantic and the west by the Appalachian Mountains, with rolling farmland in the middle, the state offers countless places to visit for history buffs, nature lovers, and passionate foodies.