4 days in Maine & Massachusetts Itinerary

4 days in Maine & Massachusetts Itinerary

Created using Inspirock United States trip itinerary builder

Make it your trip
Fly
1
Ogunquit
— 1 day
Drive
2
Boston
— 3 nights
Fly

S M T W T F S
10
11
12
13
14
15
16

Ogunquit

— 1 day
Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
Start off your visit on the 10th (Sun): enjoy the sea views from Nubble Lighthouse and then appreciate the extensive heritage of Marginal Way Walkway.

To see more things to do, maps, traveler tips, and other tourist information, read our Ogunquit trip planner.

New York City to Ogunquit is an approximately 3-hour flight. You can also drive; or take a bus. Expect slightly colder temperatures when traveling from New York City in October; daily highs in Ogunquit reach 62°F and lows reach 38°F. Wrap up your sightseeing on the 10th (Sun) early enough to drive to Boston.

Things to do in Ogunquit

Historic Sites

Side Trip

Boston

— 3 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.
You'll visit kid-friendly attractions like Boston Public Garden and Museum of Fine Arts. You'll find plenty of places to visit near Boston: Salem (Pickering Wharf, Salem Witch Museum, &more). There's much more to do: get engrossed in the history at John F. Kennedy Presidential Museum & Library, contemplate the long history of The Paul Revere House, visit North End, and browse the different shops at Faneuil Hall Marketplace.

To find reviews, ratings, other places to visit, and other tourist information, read our Boston trip tool.

Traveling by car from Ogunquit to Boston takes 1.5 hours. Alternatively, you can do a combination of taxi and train; or take a bus. Expect somewhat warmer evenings in Boston when traveling from Ogunquit in October, with lows around 50°F. Cap off your sightseeing on the 13th (Wed) early enough to catch the flight back home.

Things to do in Boston

Museums · Historic Sites · Parks · Neighborhoods

Side Trip

Maine travel guide

4.6
Beaches · Lighthouses · Mountains
The Pine Tree State
The easternmost state in New England, Maine features an indented coastline and forested interior, carved eons ago by receding glaciers. Maine includes more lighthouses and quaint resort villages than you could ever hope to explore in a single trip, but the state is also one of the country's most sparsely populated, the majority of its land pristine and uninhabited wilderness. The temperate coastal regions, historically supported by fishing and lobstering, contain most of the state's urban centers and are the most popular spots in the state for holidays. The sea is the focus here, so it shouldn't come as a surprise that water plays an important role in the distinct character of the state, shaping its economy, tourism, cuisine, politics, sports, and art.

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
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.