See the Best of Maine in Three Weeks

It’s a tough job to single out Maine’s sightseeing icons. It offers so many. Unless you have years to spend, such a big chunk of real estate needs some whittling to be made explorable. This itinerary exposes you to a good part of Maine while taking in many of the state’s icons in 20 days.

Kennebunkport, Maine, on a sunny afternoon. ©Chrisukphoto, Dreamstime.

The downside: You’ll be doing a fair bit of driving, primarily on two-lane roads where speeds through towns are often 25 mph or lower, and during the season when road construction is a fact of life. While this itinerary is planned as 20 days, if your schedule permits, you’ll be rewarded if you spend longer in any of the locations.

Book your first two nights’ lodging in Portland, then book nights 3 and 4 in Rockland or vicinity; 5 and 6 on Mount Desert Island; 7 and 8 in the Millinocket area; 9 and 10 in the Moosehead region; 11 and 12 in The Forks; 13 and 14 in Rangeley; 15 and 16 in Bethel; and 17-19 in the Sebago area.

Day 1

Stretch your legs after your journey to Maine with a refreshing walk on Ogunquit Beach, one of Maine’s prettiest and proof that there’s plenty of sand along Maine’s fabled rockbound coast. Afterward, head to Kennebunkport and indulge your passions: shopping in the boutiques and galleries that crowd Dock Square, taking a walking tour to view the historic homes, or enjoying a leisurely drive along the waterfront.

Day 2

Begin the day with a visit to Portland Head Light, a Cape Elizabeth landmark and Maine’s oldest lighthouse (1791) at the edge of 94-acre Fort Williams Park. Spend the afternoon in the Portland Museum of Art, Maine’s premier art museum, smack in the heart of the state’s largest city. End the day with a sunset cruise on Casco Bay.

Portland Head Light is a historic lighthouse in Cape Elizabeth, Maine. The light station sits on a head of land at the entrance of the primary shipping channel into Portland Harbor, which is within Casco Bay in the Gulf of Maine. Completed in 1791, it is the oldest lighthouse in the state of Maine. ©Bdingman, Dreamstime.

Day 3

Make a pilgrimage to giant sports retailer and outfitter L.L. Bean, hub of the hubbub in Freeport’s outlet bonanza. Either spend the morning shopping or taking a Walk-on Adventure class. In the afternoon, visit the Maine Maritime Museum in Bath, 10 acres of indoor and outdoor exhibits celebrating the state’s nautical heritage.

Day 4

Take a day trip to Monhegan Island from Port Clyde. This car-free, carefree gem, about a dozen miles off the coast, is laced with hiking trails and has earned a place in art history books as the Artists’ Island.

Day 5

Drive or hike to the top of Mount Battie, in Camden Hills State Park on the northern fringe of Camden. The vistas are magnificent, with the broad sweep of Penobscot Bay for a backdrop. Then continue up the coast to Mount Desert Island and begin your explorations of Acadia National Park. If you’ve arrived on the island before noon, pick up a picnic lunch and then drive the Park Loop Road, a perfect introduction to Acadia that covers many of the highlights.

Autumn sunrise in Acadia National Park, Maine, from the top of Cadillac Mountain. ©Mitgirl, Dreamstime.

Day 6

Welcome the day by watching the sunrise from the summit of Cadillac Mountain. Afterward, if you haven’t either driven or bicycled the Park Loop, do so. If you have, then explore the park: Go hiking, bicycling, or sea kayaking, take a carriage ride, or book an excursion boat to Islesford or for whale-watching.

Day 7

Depart Mount Desert Island and head inland to Millinocket, perhaps detouring to see Katahdin Iron Works but arriving in time for a late-afternoon moose safari.

Cow moose and calf at Baxter State Park, Maine. ©Gerrybill, Dreamstime.

Day 8

Venture into Baxter State Park for a day of hiking or rent a canoe and paddle one of the many lakes and rivers.

Day 9

Drive across the Golden Road to Greenville and Moosehead Lake. If time permits, continue to Rockwood and take the shuttle over to Kineo for a hike.

young deer walking on snow
Deer on Pittston Farm. Photo © Pittston Farm.

Day 10

Take a cruise on the Kate and prowl around the area, perhaps driving to Pittston Farm or hiking.

Day 11

Drive to The Forks via the Moosehead Scenic Byway and Old Canada Road National Scenic Byway and stretch your legs on a hike into Moxie Falls.

Day 12

Go white-water rafting on the Kennebec River.

Day 13

Take the scenic drive to Rangeley via Route 16, keeping an eye out for moose along the way. Work out the driving kinks with either an afternoon paddle or a hike.

Day 14

Visit the Rangeley Outdoor Sporting Heritage Museum and then take a lazy—or not—afternoon: Hike, swim, paddle, explore, or simply sit and enjoy the environment.

fall foliage lining a stream flowing through a canyon
Coos Canyon. Photo © Robert Coffey/Dreamstime.

Day 15

Head south on Route 17 over Height of Land, perhaps stopping in Coos Canyon to try your hand at panning for gold. Continue to Grafton Notch State Park.

Day 16

Prowl around Bethel’s historic district and explore the Mahoosuc section of the White Mountains.

Day 17

Snake southward through the White Mountain foothills, perhaps exploring Paris Hill, Norway, or Waterford.

Day 18

Poke around Bridgton and Naples, and perhaps take a cruise on the Songo River Queen II.

Songo Lock is the last surviving lock of the Cumberland and Oxford Canal, a 19th-century canal in southern Maine, United States. The lock is located on the Songo River, just above its confluence with the Crooked River at the northern end of Sebago Lake State Park in the town of Naples. ©Robert Rosen, Dreamstime.

Day 19

Visit the Shaker Museum, the world’s last inhabited Shaker colony, and tour Poland Spring; there’s a lot more here than bottled water.

Day 20

Head home after a dip in Sebago Lake.

Best of Maine Travel Map

Hilary Nangle

About the Author

Despite brief out-of-state interludes for college and grad school (and a stint as a ski bum), Hilary Nangle has never been able to resist the lure of her home state. She grew up on Maine’s coast, spending much of each winter skiing in the western mountains. Her sense of wanderlust was ignited when she became a Registered Maine Whitewater Guide on the Kennebec River, which gave her a chance to explore the central and northern regions of the state.

When she tired of her parents asking when she was going to get a “real job,” Hilary drew on her writing skills and began seeking out editorial work. She started out editing pro ski tour publications, then became a managing editor for a food trade publication and a features editor for a daily newspaper. Now, she freelances professionally for national magazines, newspapers, and websites.

Hilary never tires of exploring Maine, always seeking out the offbeat and quirky, and rarely resisting the invitation of a back road. To her husband’s dismay, she inherited her grandmother’s shopping gene and can’t pass a used bookstore, artisans gallery, or antiques shop without browsing. She’s equally curious about food and has never met a lobster she didn’t like. Hilary still divides her year between the coast and the mountains, residing with her husband, Tom Nangle, and an oversized dog, both of whom share her passions for long walks and Maine-made ice cream.

For updates between editions and to follow Hilary’s travels, visit mainetravelmaven.com.

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