This 6-day tour takes in some of Maine’s best museums and gallery towns, with some extra attention to Rockland and its adjacent peninsulas, where a few of Maine’s own artists did some of their best work. Note: This itinerary is designed to start on a Monday, to take advantage of various museums’ open hours, free admission days, and scheduled programs (and give you Sunday to travel home).

If your schedule doesn’t quite match up, call ahead to verify hours and closures.

Our tour starts in Ogunquit and involves a drive north to Portland via Rte. 1. It takes about 2 hours, including a detour through Cape Elizabeth with time for a picnic lunch.


Day 1, Monday: Ogunquit to Portland via Cape Elizabeth

Start the trip in seaside Ogunquit, where the Ogunquit Museum of American Art is that rarest of art-world finds: a great museum open on Monday. Ogunquit was a swingin’ artist colony in the early 20th century, and the OMAA has pieces by Walt Kuhn, Robert Laurent, Yasuo Kuniyoshi, and others who used to frequent it.

Show up right at 10am, when the museum opens, which will give you 1 1/2 hours to explore before hitting the road for Portland. En route to Portland, you could stop off for a picnic lunch at Two Lights State Park, where Edward Hopper painted his famous Lighthouse at Two Lights in 1929. (If you’d like to spend extra time in Ogunquit, skip Route 1 and Cape Elizabeth and take the I-95 toll highway to the city.)


Arrive at the Portland Museum of Art by 2pm to hop in a van for a tour of the Winslow Homer Studio at Prout’s Neck, offered on Mondays and Fridays in the summer. You’ll be back at PMA with over an hour to explore the collection before it closes; then it’s dinner and a well-earned rest in Portland.

From Portland, it’s a 30-minute drive to Brunswick via Hwy. 295. From there, we’re following coastal Rte. 1 to Bath and beyond.

Day 2, Tuesday: Brunswick and Bath

Drive to Brunswick and the Bowdoin College Museum of Art, with a wide-ranging collection that runs from Assyrian sculptures from the 9th century B.C.E. to midcentury modern furniture to interactive video installations. This jewel of a museum also holds work from big-shot Maine artists such as the Wyeths, Marsden Hartley, Winslow Homer, and John Singer Sargent.


And admission is free. Get there before lunch, so there’s time after to explore the historic campus, with many 19th-century buildings. Then it’s off to Bath and the Centre St. Arts Gallery, 11 Center Street, a collective of a couple dozen regional artists with exhibits (by both members and guest artists) that change monthly-ish. From there, detour onto Georgetown Island, southeast of town, to see the landscapes painted by the “Seguinland” artists of the early 20th century.

Bath and Rockland are separated by 45 miles of Rte. 1, but there can be heavy traffic around Wiscasset in summer; give yourself plenty of time for detours.


Day 3, Wednesday: The Road to Rockland

Following Route 1 up the coast to Rockland, take time to wander the galleries in downtown Wiscasset, especially the Wiscasset Bay Gallery, which has works from many landscape painters—among them Abraham Bogdanove and Monhegan School of Art founder Jay Hall Connaway—who were drawn to Monhegan Island in the early 20th century.

It’s also worth a detour down to Boothbay Harbor, which has several excellent galleries. Among them Gleason Fine Art stands out for its contemporary collection of artists like Maine’s Eric Hopkins, known for his bright aerial watercolors, and Jessica Lee Ives, best known for shimmering oil paintings of swimmers, boaters, fishermen, and all things wet.


En route to Rockland, before you pass through tiny Warren, call ahead to Studio JBone to see if you can tour the amazing scrap-metal sculpture garden.

After settling into your Rockland digs (some nice new hotels here), head over to the Farnsworth Art Museum, which has free admission on Wednesdays from 5–8pm throughout the summer. From Alex Katz to Robert Indiana (who did the 20-foot–high electric EAT sign on the museum’s roof) to N.C., Andrew, and Jamie Wyeth, the Farnsworth collection features giants of Maine art, past and present.


Backtrack 5 miles along Rte. 1 to Thomaston, at the crotch of the Cushing and St. George peninsulas.

Day 4, Thursday: Rockland to Port Clyde

After breakfast in Rockland, head to Thomaston, your launch point for a day exploring two adjacent and little-visited midcoast peninsulas. First, follow the winding, bucolic River Road south towards Cushing. If it’s open, detour on your way at the Langlais Sculpture Preserve, then turn right on Pleasant Point Road, and continue to Hathorne Point Road, following signs for the Olson House, the setting of Andrew Wyeth’s renowned painting Christina’s World.


Back to Thomaston for lunch, then head 20 miles south on Route 131 to spend the night in Port Clyde. Before supper, drop in on the Barbara Prey Projects gallery on Main Street. Once the town’s public house and frequented by N.C. Wyeth, it’s now a gallery space for one of Maine’s most successful commercial painters.

Day 5, Friday: Monhegan Island

Hop the Monhegan Boat Line ferry and spend a day and night discovering what once drew Edward Hopper, Robert Henri, Rockwell Kent, and others to Monhegan—along with gaggles of artists today. Hike the islands trails, duck into the small but impressive Monhegan Museum, and fraternize with locals and tourists alike at the popular Monhegan Brewing Company.


You’ll doubtless see some artists at their easels along the trail to stunning, weatherbeaten Lobster Cove; the gray house standing romantically against the waves belongs to Jamie Wyeth.

It’s 18 miles back into Rockland from the Port Clyde ferry terminal, via Rte. 131 and Rte. 1.

Day 6, Saturday: Rockland Redux

After a ferry ride back to the mainland, make it a leisurely final day back in Rockland, where the downtown hops on Saturday afternoons and there are still plenty of galleries you didn’t have time for on Wednesday. The best is the Dowling Walsh Gallery at 365 Main Street, where you can discover knockout contemporary Maine artists like Greta Van Campen, known for her design-influenced, geometric landscape paintings, and quasi-surrealist fine-art photographer Cig Harvey.


Cap off a long week at the brand new Center for Maine Contemporary Art, a glittery mod building filled with rotating exhibits in any and every media. You might end the night with a movie or a show at the historic, gloriously restored Strand Theater—it would have been 3 years old when Edward Hopper spent a formative summer here in 1926.

Come Sunday, allow 2 hours (with traffic) to backtrack to Portland via Rte. 1 and Hwy. 295. To reach the New Hampshire border and points south, give yourself 3 hours; traffic on I-95 can be a bear on summer Sundays, as folks head home.


Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.