The Perfect Coastal Maine Road Trip

At just over an hour-long flight from New York City or a two-hour drive from Boston, Maine’s largest metropolis is a great place to start. Take a leisurely walk around the harbor and Old Port, where historic brick buildings house restaurants, bars, and shops. Start by the harbor on Commercial Street and work your way up Exchange Street, which is lined with boutiques selling everything from clothes and jewelry to locally crafted pottery and fudge.

Come for bivalves on the half shell, and stay for Korean-style fried oyster buns. These guys take their shellfish seriously, but not too seriously to play with the conventions of Maine’s regional cuisine. Last year we named Eventide one of America’s best oyster bars and it’s still worth a visit.

Spend the night at the quirky new Press Hotel, an Autograph Collection Hotel, which opened in May in the Old Port. Design firm Stonehill & Taylor took inspiration from the building’s heritage as the former home of the Portland Press Herald. You’ll find playful journalism motifs peppered throughout, from the lobby installation made of antique typewriters to the custom wallpaper printed with headlines chosen by the newspaper’s editors. Each of the 110 rooms channels a 1920s writer’s office. Sitting at the vintage-inspired desk, you might feel compelled to send a postcard home.

In the morning, head toward the harbor for pastries at Portland’s must-visit artisanal bakery, which has been using locally grown, organic ingredients in their excellent baked goods for the past twenty years. The croissants, brioche, and morning buns are equally delicious. Grab some sweets to save for later—their financiers and chocolate chip cookies are the best around.

Take a slight detour to see the historic lighthouse on Cape Elizabeth, about 20 minutes south of downtown Portland. Abutting flowering fields above a rocky coastline, this classic landmark is Maine’s oldest lighthouse. George Washington commissioned it and the Marquis de Lafayette dedicated it in 1791. The Victorian Keeper’s house now serves as a museum displaying lenses and interactive exhibits.

Depart Portland and start making your way north to Rockland. After the two-hour drive, you’ll probably be hungry. Snag a waterfront table at Archer’s on the Pier, where you can watch the boats sail by. You can’t go wrong with a classic lobster roll served with hand-cut fries and coleslaw, though chef and owner Lynn Archer is best known for her King of Clubs sandwich made with lobster, bacon, lettuce, and tomato, which won the prize in Bobby Flay’s Throwdown.

Dedicated to showcasing Maine’s role in American art, the must-see Farnsworth Art Museum comprises a modern building, the Wyeth Center, the historic Farnsworth Homestead, the Olson House, and a gallery for young artists. The main building features paintings by Andrew Wyeth, George Bellows, Milton Avery, and Alex Katz, as well as sculptures by Robert Indiana. A whole room of canvases depicting ships at sea and other coastal imagery pays homage to the region and the ways it has inspired artists for centuries. Peruse the galleries in the former church up the street to see works by three generations of Wyeth painters. If you have time, take a tour of the Farnsworth Homestead, which sheds light on its 19th-century inhabitant, Lucy Farnsworth, the museum’s original benefactor.

Drive along scenic route 1 overlooking Penobscot Bay as you continue north toward Bar Harbor. You might be tempted to stop in the boutiques that line the main streets of this seaside city, but make sure to arrive at the pier in time to board the Downeast windjammer’s sunset cruise. You might be asked to help raise the sails on the four-mast vessel, then enjoy a relaxing ride around picturesque Frenchman’s Bay, which is dotted by forested islands. Bring your own wine or beer and a warm jacket—even in summer, it gets chilly on the water.

Once you’re back on dry land, head into Acadia National Park for dinner at the Jordan Pond House. The only restaurant within the park, this place is renowned for its popovers, which go very well with the lobster stew. Dinner is served inside, but if you’d like to dine outside on the lawn with a view of Jordan Pond and its distinctively sloped hills, come back for lunch or afternoon tea.

If you have room for desert—and you definitely should—head back into Bar Harbor for a cone at this creative creamery. Blueberry ice cream may be common in these parts, but Mount Desert Island Ice Cream churns one-of-a-kind flavors you won’t find anywhere else. For something subtle and refreshing, try the basil ice cream, which pairs well with a scoop of fig.

Spend the night at the cozy Asticou Inn on Mount Desert Island. This historic property dates back to 1883 and served as a home away from home for the early 20th-century affluent set that summered in Bar Harbor. The inn’s 48 rooms feature classic décor like floral wallpaper and dainty white curtains and come equipped with free WiFi. In the morning, you can go for a swim in the heated pool or play tennis and enjoy a leisurely brunch of lobster eggs benedict on the terrace.

You could spend days exploring Maine’s only national park, which comprises 35,000 acres of trails, pine-studded mountains with scenic overlooks, and beaches on Mount Desert Island. As soon as you enter this vast, gorgeous landscape, you’ll understand why prominent Americans like John D. Rockefeller Jr. and Brooke Astor vacationed here throughout the 20th century. (Rockefeller built the carriage roads that traverse the park.) Climb (or drive) to the summit of Cadillac Mountain for panoramic views of Frenchman’s Bay. Hike around Jordan Pond and the Bubbles, where the trail leads you along a wooded path and rocky outcroppings on the pond’s perimeter. Don’t miss Sand Beach, Thunder Hole, where waves crash violently against the rocks, and of course, the Bass Harbor Head lighthouse.

Make your way to the northern point of Mount Desert Island for a free tour and tasting at the Atlantic Brewing Company. Set on a ten-acre farm, this excellent craft brewery focuses exclusively on ales. Learn about the brewing process as you stand among the vats of beer, then taste a flight of their classic and seasonal brews, which run the gamut from light and crisp to rich and dark. The blueberry ale has subtle notes of the ubiquitous berry, but the true standouts are the Bar Harbor Real Ale and the Cole Porter.

Keep heading north for dinner at this no-frills seafood restaurant in nearby Ellsworth. Don’t expect anything fancy, just classic Maine dishes prepared exactly right. Lobsters are boiled in saltwater and served with drawn butter, French fries, coleslaw, and homemade bread. The fisherman’s platter arrives with a generous portion of fried scallops, clams, shrimp, and fish. Wash it down with Atlantic Brewing Company ale and finish with a slice of blueberry pie.