60 days in Maine Itinerary

60 days in Maine Itinerary

Created using Inspirock Maine journey maker
©
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

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.
Marginal Way Walkway and Mount Agamenticus will appeal to history buffs. Visiting Wells Beach and Walker's Point will get you outdoors. You'll find plenty of places to visit near Portland: Kennebunk (Gooch's Kennebunk Beach & Mother's Beach), Brunswick (Joshua L. Chamberlain Museum & Bowdoin College Museum of Art) and Kennebunkport (St. Ann's Episcopal Church, Compliments, &more). There's still lots to do: stop by Old Port, get engrossed in the history at Victoria Mansion, stroll through Boothbay Region Land Trust, and kick back and relax at Higgins Beach.

To find traveler tips, reviews, photos, and tourist information, use the Portland itinerary planner.

Lexington to Portland is an approximately 6.5-hour flight. You can also fly; or drive; or take a bus. In September, Portland is little chillier than Lexington - with highs of 73°F and lows of 52°F. Wrap up your sightseeing on the 19th (Tue) to allow time to travel to Greenville.
Parks · Outdoors · Beaches · Nature
Side Trips

Greenville — 6 nights

Greenville is a town in Piscataquis County, Maine, United States. You'll discover tucked-away gems like Baxter State Park and Mount Katahdin. Get in touch with nature at Moosehead Lake and Lily Bay State Park. Get out of town with these interesting Greenville side-trips: River Rafting & Tubing (in The Forks), Rangeley (Smalls Falls & Height of Land) and Rockwood (Borestone Mountain & Mount Kineo). The adventure continues: see Off-Road Tours, take an in-depth tour of Moosehead Historical Society, stop by Moosehead Lake Indian Store at Kamp Kamp, and admire the sheer force of Moxie Falls.

To see reviews, maps, and more tourist information, refer to the Greenville travel route builder site.

Drive from Portland to Greenville in 3 hours. Traveling from Portland in October, you will find days in Greenville are little chillier (55°F), and nights are about the same (40°F). Finish up your sightseeing early on the 25th (Mon) so you can travel to Lubec.
Parks · Nature · Wildlife · Outdoors
Side Trips

Lubec — 7 nights

Lubec is a town in Washington County, Maine, United States. You'll explore the less-touristy side of things at West Quoddy Head Light and McCurdy Smokehouse Museum. Shop till you drop at The Clutter Shop Antique and Vintage Desirables and Chapter Two Art Gallery. Venture out of the city with trips to Eastport (Raye's Mustard Mill Museum, The Mermaid - a bronze statue by Richard Klyver, &more), Machias Seal Island (in Jonesport) and Petit Manan National Wildlife Refuge (in Hancock). There's lots more to do: stroll through Bog Brook Cove Preserve, take your sightseeing to a higher altitude at Klondike Mountain, explore the striking landscape at The Bold Coast, and kick back and relax at Jasper Beach.

For photos, reviews, other places to visit, and more tourist information, go to the Lubec online trip maker.

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. Cap off your sightseeing on the 1st (Mon) early enough to go by car to Bar Harbor.
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. Get some historical perspective at St. Saviour's Church : and Egg Rock Light. Museum-lovers will get to explore Cole Land Transportation Museum and Wendell Gilley Museum. Explore the numerous day-trip ideas around Bar Harbor: Bass Harbor (Bass Harbor Head Lighthouse & Ship Harbor Nature Trail), Wonderland Trail (in Southwest Harbor) and Winter Harbor (Whopaints, Schoodic Point, &more). And it doesn't end there: tour the pleasant surroundings at Carriage Roads, hit the best photo ops around with an inspiring photography tour, trek along Ocean Path, and walk around Agamont Park.

To see maps, ratings, reviews, and other tourist information, use the Bar Harbor online tour itinerary maker.

Traveling by car from Lubec to Bar Harbor takes 2.5 hours. November in Bar Harbor sees daily highs of 46°F and lows of 30°F at night. Finish your sightseeing early on the 15th (Mon) to allow enough time to drive to Rockland.
Parks · Outdoors · Trails · Museums
Side Trips

Rockland — 9 nights

Rockland is a city in Knox County, Maine, in the United States. Visit Pemaquid Point Lighthouse and Rockland Breakwater Light for their historical value. Museum-lovers will appreciate Farnsworth Art Museum and Maine Lighthouse Museum. Explore Rockland's surroundings by going to Colonial Pemaquid State Historic Site (in New Harbor), Belfast (Belfast Harborwalk & Belfast Historical Society & Museum) and Marshall Point Lighthouse Museum (in Port Clyde). And it doesn't end there: explore the world behind art at Colby College Museum of Art, cast your line with A Morning In Maine, examine the collection at Sail Power and Steam Museum, and look for gifts at Owls Head Lighthouse.

To find maps, photos, and other tourist information, read Rockland trip itinerary website.

Drive from Bar Harbor to Rockland in 2.5 hours. Alternatively, you can drive; or take a bus. In November, daytime highs in Rockland are 47°F, while nighttime lows are 30°F. Wrap up your sightseeing on the 24th (Wed) to allow time to fly back home.
Museums · Historic Sites · Parks · Wildlife
Side Trips

Maine travel guide

4.6
Beaches · Lighthouses · Gift & Specialty Shops
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.