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.
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.
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.
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.
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.
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.
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.
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.
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.
Venture into Baxter State Park for a day of hiking or rent a canoe and paddle one of the many lakes and rivers.
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.
Take a cruise on the Kate and prowl around the area, perhaps driving to Pittston Farm or hiking.
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.
Go white-water rafting on the Kennebec River.
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.
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.
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.
Prowl around Bethel’s historic district and explore the Mahoosuc section of the White Mountains.
Snake southward through the White Mountain foothills, perhaps exploring Paris Hill, Norway, or Waterford.
Poke around Bridgton and Naples, and perhaps take a cruise on the Songo River Queen II.
Visit the Shaker Museum, the world’s last inhabited Shaker colony, and tour Poland Spring; there’s a lot more here than bottled water.
Head home after a dip in Sebago Lake.