5 days in Maine Itinerary

5 days in Maine Itinerary

Created using Inspirock Maine trip itinerary maker

Make it your trip
— 2 nights
Bar Harbor, Mount Desert Island
— 2 nights



— 2 nights

The Forest City

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.
Get out of town with these interesting Portland side-trips: Nubble Lighthouse (in York) and Ogunquit ( PANACHE FINE JEWELRY AND ART GALLERY & Marginal Way Walkway). The adventure continues: sample the tasty concoctions at Allagash Brewing Company, get a taste of local nightlife at Maine Craft Distilling, sample some tasty brews at a beer tour and tasting, and visit a coastal fixture at Portland Head Light.

To see traveler tips, more things to do, photos, and other tourist information, use the Portland online sightseeing planner.

Newark to Portland is an approximately 3.5-hour flight. You can also drive; or do a combination of train and bus. Prepare for a bit cooler weather when traveling from Newark in October: high temperatures in Portland hover around 62°F and lows are around 43°F. Wrap up your sightseeing on the 12th (Tue) to allow time to drive to Bar Harbor.

Things to do in Portland

Historic Sites · Breweries & Distilleries · Tours · Wildlife

Side Trips

Find places to stay Oct 10 — 12:

Bar Harbor, Mount Desert Island

— 2 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. On the 13th (Wed), trek along Cadillac Mountain North Ridge Trail, take your sightseeing to a higher altitude at Cadillac Mountain, and then go for a walk through Compass Harbor Trail. Get ready for a full day of sightseeing on the 14th (Thu): take a memorable drive along Park Loop Road and then get a new perspective on things with Boat Tours & Water Sports.

To find ratings, photos, more things to do, and tourist information, you can read our Bar Harbor journey builder app.

You can drive from Portland to Bar Harbor in 3.5 hours. Other options are to drive; or do a combination of bus and flight; or take a bus. In October, daytime highs in Bar Harbor are 59°F, while nighttime lows are 42°F. Wrap up your sightseeing on the 14th (Thu) to allow time to fly back home.

Things to do in Bar Harbor

Outdoors · Parks · Tours · Nature

Side Trip

Find places to stay Oct 12 — 14:

Maine travel guide

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.