60 days in Maine Itinerary

60 days in Maine Itinerary

Created using Inspirock Maine trip planner

©
Make it your trip
Fly
1
Portland
— 23 nights
Drive
2
Greenville
— 6 nights
Drive
3
Lubec
— 7 nights
Drive
4
Bar Harbor, Mount Desert Island
— 14 nights
Drive
5
Rockland
— 9 nights
Fly

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Portland

— 23 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.
Popular historic sites such as Marginal Way Walkway and Spring Point Ledge Lighthouse are in your itinerary. You'll enjoy a bit of beach vacationing at Wells Beach and Popham Beach State Park. Venture out of the city with trips to Kennebunkport (St. Ann's Episcopal Church, Compliments, &more), Kennebunk (Gooch's Kennebunk Beach & Mother's Beach) and Brunswick (Joshua L. Chamberlain Museum & Bowdoin College Museum of Art). And it doesn't end there: contemplate the long history of Wadsworth-Longfellow House, stroll through Long Sands Beach, enjoy the sea views from Portland Breakwater Lighthouse, and see the interesting displays at Maine Maritime Museum.

To find reviews, maps, other places to visit, and tourist information, go to the Portland trip planner.

Lexington to Portland is an approximately 6.5-hour flight. You can also fly; or drive; or take a bus. Expect little chillier temperatures when traveling from Lexington in September; daily highs in Portland reach 73°F and lows reach 52°F. Wrap up your sightseeing on the 6th (Wed) to allow time to travel to Greenville.

Things to do in Portland

Parks · Outdoors · Beaches · Nature

Side Trips

Greenville

— 6 nights
Greenville is a town in Piscataquis County, Maine, United States. Do some cultural sightseeing at Height of Land and Moosehead Historical Society. Eschew the tourist crowds and head to Baxter State Park and River Rafting & Tubing. Get out of town with these interesting Greenville side-trips: Smalls Falls (in Rangeley), Mount Katahdin (in Millinocket) and Rockwood (Borestone Mountain & Mount Kineo). There's lots more to do: admire the majestic nature at Mount Kineo State Park, get engrossed in the history at Katahdin Cruises and Moosehead Marine Museum, explore the activities along Moosehead Lake, and admire the sheer force of Moxie Falls.

For maps, ratings, traveler tips, and tourist information, use the Greenville trip planner.

You can drive from Portland to Greenville in 3 hours. Traveling from Portland in October, expect nights in Greenville to be about the same, around 40°F, while days are slightly colder, around 55°F. Finish up your sightseeing early on the 12th (Tue) so you can travel to Lubec.

Things to do in Greenville

Parks · Nature · Wildlife · Outdoors

Side Trips

Lubec

— 7 nights
Lubec is a town in Washington County, Maine, United States. Head to The Clutter Shop Antique and Vintage Desirables and Chapter Two Art Galleryfor plenty of shopping. McCurdy Smokehouse Museum and Ruggles House will appeal to museum buffs. Venture out of the city with trips to Eastport (Raye's Mustard Mill Museum, The Mermaid - a bronze statue by Richard Klyver, &more), Petit Manan National Wildlife Refuge (in Hancock) and Machias Seal Island (in Jonesport). There's much more to do: visit a coastal fixture at West Quoddy Head Light, tour the pleasant surroundings at Moosehorn National Wildlife Refuge, enjoy the sand and surf at Jasper Beach, and immerse yourself in nature at Cobscook Bay State Park.

To see more things to do, maps, reviews, and tourist information, read Lubec online travel planner.

You can drive from Greenville to Lubec in 4 hours. October in Lubec sees daily highs of 59°F and lows of 42°F at night. Wrap up your sightseeing on the 19th (Tue) early enough to drive to Bar Harbor.

Things to do in Lubec

Parks · Nature · Wildlife · Shopping

Side Trips

Bar Harbor, Mount Desert Island

— 14 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Give yourself a bit of retail therapy at Nervous Nellie's Jams and Jellies and Works of Hand. Step out of the city life by going to Shore Path and Sand Beach. You'll find plenty of places to visit near Bar Harbor: Winter Harbor (Whopaints Gallery & Schoodic Point), Bass Harbor (Bass Harbor Head Lighthouse & Ship Harbor Nature Trail) and Wonderland Trail (in Southwest Harbor). There's much more to do: enjoy the sea views from Egg Rock Light, stroll around Agamont Park, stroll through Carriage Roads, and hike along Champlain Mountain & Beehive Loop Trail.

To see ratings, maps, more things to do, and more tourist information, use the Bar Harbor driving holiday planning site.

You can drive from Lubec to Bar Harbor in 2.5 hours. In October, daytime highs in Bar Harbor are 59°F, while nighttime lows are 42°F. Finish your sightseeing early on the 2nd (Tue) so you can drive to Rockland.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Museums

Side Trips

Rockland

— 9 nights
Rockland is a city in Knox County, Maine, in the United States. Do some cultural sightseeing at Pemaquid Point Lighthouse and Rockland Breakwater Light. You'll discover tucked-away gems like Camden Hills State Park and Owls Head Lighthouse. Venture out of the city with trips to Belfast (Belfast Harborwalk & Belfast Historical Society & Museum), Marshall Point Lighthouse Museum (in Port Clyde) and Colonial Pemaquid State Historic Site (in New Harbor). There's much more to do: cast your line with Morning In Maine Boat Tour, admire the masterpieces at Farnsworth Art Museum, wander the streets of High Street Historic District, and examine the collection at Sail Power and Steam Museum.

To find where to stay, maps, more things to do, and tourist information, read our Rockland online journey builder.

You can drive from Bar Harbor to Rockland in 2.5 hours. Another option is to take a bus. In November, daytime highs in Rockland are 47°F, while nighttime lows are 30°F. Finish your sightseeing early on the 11th (Thu) so you can fly back home.

Things to do in Rockland

Museums · Historic Sites · Parks · Wildlife

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.