Best of Maine Itinerary

This itinerary loops though coastal and inland Maine, taking in many of the state’s iconic sights. The downside: You’ll be doing a fair bit of driving, primarily on two-lane roads where speeds are often 25 mph (40 kph) or lower, and during the season when road construction is a fact of life. While this itinerary is planned as 11 days, you’ll be rewarded if you spend more time lingering.

Book your first two nights’ lodging in Portland, then book nights 3 and 4 in Rockland or its vicinity; 5 and 6 on Mount Desert Island; 7 and 8 in the Moosehead region; 9 in Rangeley; and 10 in Bethel.

sunset on the rocky coast with a lighthouse
Portland Head Lighthouse. Photo © Sara Winter/123rf.

Portland and Vicinity

Day 1: Kennebunkport

Stretch your legs after your journey to Maine with a walk on Kennebunkport’s Goose Rocks Beach, one of Maine’s prettiest. Afterward, mosey along the waterfront to Dock Square, where former fishing shacks are now boutiques and galleries, and perhaps indulge in a lobster roll at the Clam Shack.

Day 2: Portland

30 miles/48 km; 45 minutes

Begin the day with a visit to Portland Head Light, a Cape Elizabeth landmark and Maine’s oldest lighthouse (1791), perched on the cliffs of 94-acre (38-ha) Fort Williams Park. Spend a few hours in the Portland Museum of Art, Maine’s premier art museum, and then prowl through the Old Port and the Waterfront. End the day with a sunset cruise on Casco Bay.

Day 3: Freeport and Bath

35 miles/56 km; 1 hour

Make a pilgrimage to giant sports retailer and outfitter L. L. Bean, hub of the hubbub in Freeport’s outlet bonanza. Spend a few hours shopping or taking a class at the L. L. Bean Outdoor Discover School. In the afternoon, visit the Maine Maritime Museum in Bath, comprising 10 acres (4 ha) of indoor and outdoor exhibits celebrating the state’s nautical heritage.

Rockland and Vicinity

Day 4: Greater Rockland

45 miles/72 km; 1 hour

Image of calm water by beach with red boat in the foreground
Monhegan Island. Photo © Sharon Cobo/Dreamstime

Explore Greater Rockland’s many museums and lighthouses. Or take a day trip to Monhegan Island from Port Clyde. This car-free, carefree gem, about a dozen miles (19 km) off the coast, is laced with hiking trails and has earned renown as the Artists’ Island. End the day at the classic McLoon’s Lobster Shack.

Day 5: Camden and Acadia

85 miles/137 km; 2.25 hours

Drive or hike to the top of Mount Battie in Camden Hills State Park, on the northern fringe of Camden. You’ll get a magnificent view of Penobscot Bay. Then continue up the coast to Mount Desert Island and begin your explorations of Acadia National Park.

Acadia National Park

Day 6: Mount Desert Island

sunrise over cadillac mountain in acadia
Sunrise over Cadillac Mountain. Photo © Jon Bilous/Dreamstime.

Welcome the day by watching the sunrise from the summit of Cadillac Mountain. Afterward, before the crowds arrive, drive the Park Loop Road, which covers many of Acadia’s highlights. Immerse yourself in the park by going hiking, bicycling, sea kayaking, or on a carriage ride.

Maine Highlands

Day 7-8: Greenville and Moosehead Lake

130 miles/210 km; 2.75 hours

Depart Mount Desert Island and head inland to Greenville and Moosehead Lake. If time permits, continue to Rockwood and take the shuttle to Kineo for a hike.

Book a sunrise or sunset moose safari. In the afternoon, enjoy a cruise on the Kate and prowl around the area. End the day with dinner at one of the area’s road-accessible sporting camps.

The Forks to Rangeley

Day 9: The Forks and Rangeley

165 miles/265 km; 3.5 hours

Distant view of a tall, tumbling waterfall with autumnal trees at the top
Moxie Falls. Photo © Jon Bilous/Dreamstime.

Depart Greenville and drive to The Forks via the Moosehead Scenic Byway and Old Canada Road National Scenic Byway, perhaps taking a break to stretch your legs on the easy hike into Moxie Falls. (Add a day here if you want to go white-water rafting on the Kennebec River.) Continue the scenic drive to Rangeley, arriving in time to learn about the region’s history at the Rangeley Outdoor Sporting Heritage Museum.

Day 10: Rangeley

60 miles/97 km; 1.25 hours

After a morning hiking, paddling, or fishing, head south on Route 17 over Height of Land, perhaps stopping in Coos Canyon to try your hand at panning for gold. Detour off the main road in Newry to see the Artist’s Covered Bridge.

Day 11: Gems of Route 26

75 miles/120 km; 1.75 hours

Snake southward through the White Mountain foothills, perhaps exploring Paris Hill or Norway; the Shaker Museum, the world’s last inhabited Shaker colony; or Poland Spring (there’s more here than bottled water). Make the one-hour drive back to Portland.

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

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Image of lighthouse at sunset with text 11-Day Best of Maine Itinerary