8 days in Boston, Rockland & Bangor Itinerary

8 days in Boston, Rockland & Bangor Itinerary

Created using Inspirock United States trip itinerary planner

Make it your trip
Fly
1
Boston
— 4 nights
Fly
2
Rockland
— 2 nights
Drive
3
Bangor
— 1 night
Fly

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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 cultural insight at Trinity Church and Minute Man National Historical Park. Visit Louisa May Alcott's Orchard House and Mount Auburn Cemetery for their historical value. Step out of Boston with an excursion to Sleepy Hollow Cemetery in Concord--about 36 minutes away. The adventure continues: take an in-depth tour of Buckman Tavern, get to know the fascinating history of HarborWalk, steep yourself in history at Charlestown Navy Yard, and buy something for everyone on your list at Prudential Center.

To find more things to do, photos, other places to visit, and other tourist information, use the Boston road trip planning website.

New Orleans to Boston is an approximately 5-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from New Orleans to Boston. Plan for little chillier nights when traveling from New Orleans in October since evenings lows in Boston dip to 50°F. Wrap up your sightseeing on the 5th (Tue) early enough to fly to Rockland.

Things to do in Boston

Historic Sites · Shopping · Breweries & Distilleries · Neighborhoods

Side Trips

Rockland

— 2 nights
Rockland is a city in Knox County, Maine, in the United States. On the 5th (Tue), examine the collection at Owls Head Transportation Museum, then enjoy the sea views from Rockland Breakwater Light, and then stop by Maine State Prison Store. Get ready for a full day of sightseeing on the next day: admire the masterpieces at Farnsworth Art Museum, walk around Buoy Park, and then learn more about the world around you at Maine State Museum.

To find ratings, where to stay, maps, and tourist information, use the Rockland road trip planning website.

You can fly from Boston to Rockland in 3 hours. Alternatively, you can drive; or take a bus. Expect a bit cooler temperatures when traveling from Boston in October; daily highs in Rockland reach 58°F and lows reach 42°F. Wrap up your sightseeing on the 7th (Thu) early enough to drive to Bangor.

Things to do in Rockland

Museums · Historic Sites · Shopping · Parks

Side Trips

Bangor

— 1 night
Bangor is a city along the Penobscot River in the U.S. state of Maine. On the 7th (Thu), stroll through Kenduskeag Stream Heritage Trail, try to win big at Hollywood Raceway, then explore the engaging exhibits at Maine Discovery Museum, and finally sample the tasty concoctions at 2 Feet Brewing. Get ready for a full day of sightseeing on the 8th (Fri): take in the exciting artwork at the rock & art shop, buy something for everyone on your list at Bangor Mall, then indulge your thirst for a good beer at Orono Brewing Company, and finally make a trip to Stephen King's House.

To find other places to visit, where to stay, photos, and other tourist information, refer to the Bangor journey website.

Drive from Rockland to Bangor in 2 hours. Alternatively, you can take a bus. October in Bangor sees daily highs of 61°F and lows of 40°F at night. Wrap up your sightseeing on the 8th (Fri) early enough to fly back home.

Things to do in Bangor

Museums · Shopping · Breweries & Distilleries · Childrens Museums

Side Trip