28 days in Maine Itinerary

28 days in Maine Itinerary

Created using Inspirock Maine trip maker
©
Make it your trip
Fly
1
Portland
— 5 nights
Drive
2
Boothbay Harbor
— 6 nights
Drive
3
Rangeley
— 5 nights
Drive
4
Bangor
— 4 nights
Drive
5
Bar Harbor, Mount Desert Island
— 7 nights
Fly

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Portland — 5 nights

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), York Beach (York's Wild Kingdom Zoo and Fun Park & Long Sands Beach) and Ogunquit (Perkins Cove, Marginal Way Walkway, &more). There's still lots to do: visit a coastal fixture at Portland Head Light, enjoy breathtaking views from Portland Observatory, explore the world behind art at Portland Museum of Art, and get a new perspective on things with Boat Tours & Water Sports.

To see traveler tips, photos, reviews, and other tourist information, use the Portland tour itinerary planner.

Chicago to Portland is an approximately 4-hour flight. You can also drive; or take a bus. You'll lose 1 hour traveling from Chicago to Portland due to the time zone difference. Plan for a bit cooler temperatures traveling from Chicago in September, with highs in Portland at 73°F and lows at 52°F. Finish your sightseeing early on the 11th (Sun) so you can drive to Boothbay Harbor.
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Parks · Historic Sites · Outdoors · Breweries & Distilleries
Side Trips

Boothbay Harbor — 6 nights

Boothbay Harbor is a town in Lincoln County, Maine, United States. Change things up with these side-trips from Boothbay Harbor: Seagull Cottage (in Rockland), Pemaquid Point Lighthouse (in Bristol) and Camden (Camden Hills State Park, Mount Battie, &more). There's lots more to do: get up close to creatures of the deep with Cap'n Fish's Cruises, see the interesting displays at Owls Head Transportation Museum, take an in-depth tour of Boothbay Region Historical Society Museum, and take in the exciting artwork at Ed Brown's Wharfside Gallery.

To find where to stay, ratings, other places to visit, and more tourist information, go to the Boothbay Harbor trip planner.

Traveling by car from Portland to Boothbay Harbor takes 1.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of train and taxi. September in Boothbay Harbor sees daily highs of 73°F and lows of 51°F at night. Wrap up your sightseeing on the 17th (Sat) to allow time to drive to Rangeley.
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Parks · Museums · Wildlife · Nature
Side Trips

Rangeley — 5 nights

Rangeley is a town in Franklin County, Maine, USA. The population was 1,168 at the 2010 census. You'll find plenty of places to visit near Rangeley: Grafton Notch State Park (in Bethel), Jackman (Jackman Trading Post & Moose River) and Tumbledown Mountain (in Weld). There's much more to do: cruise along Height of Land, cast your line with Dead River Expeditions, take in the awesome beauty at Bald Mountain, and admire the sheer force of Moxie Falls.

To see more things to do, reviews, and tourist information, use the Rangeley online journey planner.

Drive from Boothbay Harbor to Rangeley in 2.5 hours. Alternatively, you can drive. Expect a bit cooler evenings in Rangeley when traveling from Boothbay Harbor in September, with lows around 45°F. Cap off your sightseeing on the 22nd (Thu) early enough to go by car to Bangor.
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Parks · Nature · Outdoors · Wildlife
Side Trips

Bangor — 4 nights

Bangor is a city along the Penobscot River in the U.S. state of Maine. You'll find plenty of places to visit near Bangor: The Granite Garden Gallery (in Sullivan), Tree Spirits (in Oakland) and Colby College Museum of Art (in Waterville). There's still lots to do: stroll the grounds of Mount Hope Garden Cemetery, see the interesting displays at Bucksport Historical Society, look for all kinds of wild species at Orono Bog Boardwalk, and don't miss a visit to Stephen King's House.

For photos, reviews, maps, and tourist information, use the Bangor online sightseeing planner.

You can drive from Rangeley to Bangor in 2.5 hours. Another option is to drive. Traveling from Rangeley in September, expect somewhat warmer with lows of 51°F in Bangor. Cap off your sightseeing on the 26th (Mon) early enough to go by car to Bar Harbor.
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Museums · Parks · Wineries · Historic Sites
Side Trips

Bar Harbor, Mount Desert Island — 7 nights

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Go for a jaunt from Bar Harbor to Winter Harbor to see Schoodic Point about 46 minutes away. There's still lots to do: take a tour by water with Boat Tours & Water Sports, explore the activities along Frenchman Bay, trek along Precipice Trail, and look for all kinds of wild species at Shore Path.

Plan my Bar Harbor trip by asking Inspirock to come up with tips and suggestions.

Drive from Bangor to Bar Harbor in 1.5 hours. Alternatively, you can take a bus. In September, daily temperatures in Bar Harbor can reach 70°F, while at night they dip to 52°F. Wrap up your sightseeing on the 3rd (Mon) to allow time to fly back home.
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Parks · Outdoors · Nature · Trails
Side Trips

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.
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