4 days in New York City, Maine & Massachusetts Itinerary

4 days in New York City, Maine & Massachusetts Itinerary

Created using Inspirock United States tour itinerary builder

Make it your trip
New York City
— 2 nights
— 1 night
— 1 day


New York City

— 2 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Bring the kids along to Central Park and The High Line. There's still lots to do: take in panoramic vistas at Empire State Building, don't miss a visit to Times Square, explore the world behind art at The Metropolitan Museum of Art, and pause for some photo ops at 9/11 Memorial.

To find traveler tips, photos, more things to do, and other tourist information, read our New York City trip maker.

Newark to New York City is an approximately 1-hour car ride. You can also take a train; or take a bus. Traveling from Newark in October, you can expect nighttime temperatures to be a bit warmer in New York City, with lows of 57°F. Finish your sightseeing early on the 12th (Tue) to allow enough time to fly to Ogunquit.

Things to do in New York City

Parks · Museums · Neighborhoods · Historic Sites


— 1 night
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.
To see other places to visit, ratings, traveler tips, and other tourist information, you can read our Ogunquit trip itinerary planning tool.

You can fly from New York City to Ogunquit in 3 hours. Other options are to drive; or take a bus. Prepare for a bit cooler weather when traveling from New York City in October: high temperatures in Ogunquit hover around 62°F and lows are around 38°F. On the 13th (Wed), you're off to Boston.

Things to do in Ogunquit

Outdoors · Parks · Tours · Shopping


— 1 day


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.
On the 13th (Wed), explore the world behind art at Museum of Fine Arts, then take in the architecture and atmosphere at Trinity Church, then get engrossed in the history at John F. Kennedy Presidential Museum & Library, and finally get to know the fascinating history of Louisburg Square.

To see photos, other places to visit, ratings, and more tourist information, read Boston online road trip planner.

Drive from Ogunquit to Boston in 1.5 hours. Alternatively, you can do a combination of taxi and train; or take a bus. Traveling from Ogunquit in October, Boston is a bit warmer at night with lows of 50°F. Finish your sightseeing early on the 13th (Wed) to allow enough time to fly back home.

Things to do in Boston

Museums · Historic Sites

Maine travel guide

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

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.