Begin in Brunswick, Maine’s oldest college town, where Bowdoin College was founded in 1794. Maine Street is a full 12 rods wide—just as it was when the town was laid out in 1717. Today, it’s lined with quaint shops brimming with nautical themes. Enjoy your choice of B&Bs, many converted from the stately residences of schooner captains from a bygone era.
Continue up Route 1 to Bath, home to modern-day shipbuilder Bath Iron Works as well as the 19th-century Percy and Small Shipyard—which, in its heyday, launched over forty-two schooners, including the Wyoming, the largest wooden ship ever built in America. The shipyard is now the site of the family-oriented Maine Maritime Museum. Travel through 400 years of Maine history documenting its connection to the sea. While in Bath, explore the brick-and-granite downtown of shops, pubs and magnificent restaurants. Stroll by the grand old sea captains’ homes on Washington, High and Middle Streets, some of which now serve as inns and B&Bs.
From Route 1 in Bath, take Route 209 south down the 10-mile Phippsburg Peninsula, where you’ll find Fort Popham, a massive granite structure built to protect Bath’s shipbuilding interests during the Civil War. Not to be missed is nearby Popham Beach State Park, which features one of Maine’s most glorious—and popular—sandy beaches.
Return to Bath and head north on Route 1 to Wiscasset. This charming village is situated on a hillside sloping gently towards the Sheepscot River; lining the streets are antique shops, galleries and restaurants. Several historic homes—including the fanciful 1852 Musical Wonder House, which features an amazing collection of musical machines—are open to the public, and offer glimpses of the town’s 18th- and 19th-century shipping prosperity.
From there, head south on Route 27 to Boothbay Harbor, where shops, restaurants, inns and chowder-houses surround the snug harbor. During your stay, take in the Boothbay Railway Village, enjoy a whale-watching cruise, a day-sail or a visit to a nearby island.
From Boothbay, take Route 27 back to Route 1 and head north to Damariscotta and Newcastle. The main street connecting these villages is lined with 19th-century storefronts, housing shops, pubs, restaurants, galleries and an old-fashioned drugstore, complete with a ‘50s-style soda fountain. While in town, visit the Round Top Center for the Arts (open through Columbus Day), a 1924 farm offering cultural events, as well as ovation-worthy ice cream.
Also of interest is circa-1808 St. Patrick’s, New England’s oldest surviving Catholic church; the steeple houses a Paul Revere bell. The nearby Damariscotta Mills area features extraordinary homes as well as the local “swimming hole” on Damariscotta Lake—look for a pair of bald eagles that nest on its shore. Before moving on, enjoy a stay at one of the area’s charming inns.
From Damariscotta, take Route 130 through Bristol and the fishing village of New Harbor (stop along the way for a lobster!) to the bold Pemaquid Point Lighthouse, situated atop a wide stretch of wave-buffeted rocky coast. This grand old beacon has guided mariners since 1827; its history and that of the local fishing industry is chronicled in the Fishermen’s Museum (open through Columbus Day) in the former lighthouse-keeper’s quarters.
From Bristol, head north on Route 32 to Waldoboro where you’ll find the Old German Meeting House, circa 1772, complete with square-benched pews and a wineglass-shaped pulpit. Take a short diversion onto Route 220 to Friendship and visit the Friendship Museum—a converted schoolhouse dedicated to the history of world-renowned Friendship Sloops.
Head north on Route 97 back to Route 1 and through Thomaston where you’ll take a right onto Route 131. Head down to Port Clyde. Highly recommended is a 90-minute ferry ride (watch for dolphins, whales and seals en route) to Monhegan Island, believed by many to be one of Maine’s most enchanting destinations. Artists such as George Bellows, Rockwell Kent, Edward Hopper and Jamie Wyeth have found inspiration here; the Island’s creative tradition can be seen today in the dozens of artists’ and artisans’ studios that welcome visitors. Monhegan’s network of trails leads to sea cliffs, quiet coves and a magnificent pine forest, and its quaint inns provide wonderful bases from which to explore. This is the quintessential Maine island.
After your island jaunt, head back up 131 and pick up Route 1 north to Rockland, the homeport for several members of Maine’s windjammer fleet. To tour Maine’s scenic beauty on land, visit the nationally recognized Farnsworth Art Museum, which houses a significant collection of Maine landscape paintings.
In addition, works by the “first family” of Maine painting—N.C., Andrew and Jamie Wyeth—are displayed in the Farnsworth’s Wyeth Center, designed (down to the window shutter knobs) with the help of the Wyeths themselves. The Olson House in nearby Cushing (open for tours) was the setting for many of Andrew Wyeth’s paintings, includingChristina’s World.
After a stay in Rockland, continue to Camden via Route 1 north. Here, the Camden Hills, ablaze in fall color, slope dramatically to the harbor. In 1912, Maine poet Edna St. Vincent Millay reflected on this mountains-to-the-sea landscape: "All I could see from where I stood/Was three long mountains and a wood;/I turned and looked the other way,/And saw three islands in a bay." Today, you can drive to the 800-foot summit of Mt. Battie to take in the poet’s grand view of the hills and Penobscot Bay.
Stroll through Camden’s picturesque downtown to enjoy shops, harborside restaurants and pubs, stopping along the way to enjoy the views from Harbor Park, designed by the same firm that planned New York’s Central Park. Across the street is the Camden Amphitheater, an open-air stage that hosts plays and musical performances. Camden also offers a wealth of exquisite homes-turned-inns, many with stunning views of the harbor.
Continue up Route 1 north to Belfast, where a Victorian downtown boasts fine old houses and great shops. During your stay, take a side trip to nearby Searsport, which, in the 1800s, was home to more sea captains than any other American community its size. The Penobscot Marine Museum, housed in buildings that once made up the town’s center, pays tribute to these adventurous men who earned their fortunes sailing out of Penobscot Bay to ports-of-call around the world.
One more side trip will be well worth your while. Continue up Route 1 to Prospect, where you will see the towers of the newly built Penobscot Narrows Bridge and Observatory soaring above the treeline. The 440-foot high Observatory is open to the public via a swift elevator, providing a spectacular 360-degree panoramic view of the surrounding hills, river and bay.
Circle back to Belfast, take Route 137 to Route 220 north to the town of Unity. The foliage rich trips take you past streams and lakes, highlighting the natural beauty of Maine.
Afterwards, head back down Route 220 and pick up Route 173 in Liberty, which brings you to Searsmont and Route 131. Follow 131 to Route 17 west. Take Route 206 southbound through Jefferson, and then Route 213 to 194 up to Alna and Head Tide. Explore this area carefully, as you might find gems such as an old closed general store with windows that, when peered through, transport your imagination back in time—to when folks sat by the wood stove, playing checkers and conversing with their neighbors. To complete this autumn trip, head back down Route 218 to Wiscasset.