Itineraries: Great American Drives

The Maine Coast: Portland to Eastport

Lighthouses, lobster shacks, Acadia — and the first sunrise in the contiguous United States.

5 Days4 nights

~285 miUS Route 1

6 Lighthouses& counting

1 Soundtrackwritten for this road

Route 1 doesn't rush, and neither should you. Five days from Portland's working waterfront to Eastport — the easternmost city in the United States — with an overnight in every region that deserves one. Explore as you go. The road will tell you where to stop.

DAY 1

Portland → Boothbay Harbor

~60 MI · 1.5 HRS DRIVING

Portland Head LightMaine's oldest lighthouse (1791), on the cliffs of Cape Elizabeth. Go early — the light faces the sunrise.

Wiscasset"The Prettiest Village in Maine." The line at Red's Eats is part of the experience — the lobster roll is the reward.

Boothbay HarborWalk the footbridge at golden hour and watch the fleet come home.

🌙 Overnight: Boothbay Harbor Region ♪ Song for this stretch — coming to the soundtrack Book Your Ride →

DAY 2

Boothbay → Rockland · Rockport · Camden

~50 MI · EASY DAY

Coastal Maine Botanical Gardens300 acres and the famous giant trolls hiding in the woods. Mornings are quietest.

Pemaquid Point LighthouseThe one on Maine's state quarter. The striped rock ledges below are the photograph.

Rockland BreakwaterWalk nearly a mile of granite blocks straight out to sea to reach the lighthouse at the end.

Mount Battie, CamdenDrive up for the postcard view of Camden Harbor — save it for sunset.

🌙 Overnight: Rockland / Rockport / Camden Region ♪ Song for this stretch — coming to the soundtrack Book Your Ride →

Like where this is going?

The full itinerary has the timing, the food, the photo spots, and the soundtrack.

Get the Full Itinerary + Soundtrack

DAY 3

Camden → Ellsworth → Bar Harbor

~75 MI · 2 HRS DRIVING

BelfastA working harbor town with a great main street — the coffee stop of the trip.

Penobscot Narrows Observatory & Fort KnoxRide the elevator 420 feet up a bridge tower — the tallest public bridge observatory in the world — then wander the granite fort below.

Bar Harbor Shore PathArrive on Mount Desert Island, park once, and walk the shoreline past the Porcupine Islands.

🌙 Overnight: Ellsworth / Acadia / Bar Harbor Region ♪ Song for this stretch — coming to the soundtrack Book Your Ride →

DAY 4

Acadia → The Bold Coast → Lubec

~100 MI · 2.5 HRS DRIVING

Cadillac Mountain SunrisePart of the year, this is the first place the sun touches the United States. Reserve your vehicle pass ahead.

Park Loop Road & Thunder HoleAcadia's greatest hits in one morning loop — time Thunder Hole for a rising tide.

The Bold CoastRoute 1 empties out past Machias. This is the Maine most visitors never see — blueberry barrens and open sea.

West Quoddy Head LightThe candy-striped lighthouse at the easternmost point of the U.S. mainland.

Campobello Island, NBFDR's summer cottage is just over the bridge from Lubec. Bring your passport.

🌙 Overnight: Lubec / Campobello / Eastport Region ♪ Song for this stretch — coming to the soundtrack Book Your Ride →

DAY 5

Eastport — The Edge of America

~40 MI · THEN HOMEWARD

First Sunrise in AmericaBe on the Eastport breakwater before dawn. You'll have it nearly to yourself.

The Old SowThe largest tidal whirlpool in the Western Hemisphere churns just offshore — best viewed a few hours before high tide.

Raye's Mustard MillAmerica's last stone-ground mustard mill, running since 1900. Yes, there are samples.

🏁 Trip complete: corner to corner, you made it ♪ Song for this stretch — coming to the soundtrack Book Your Ride →

Get the Full Itinerary + Soundtrack

This page is the free preview. The full edition is the trip in your hands — a beautiful, printable, photo-filled guide paired with original songs written for this exact stretch of road.