Scenic Summer Drive from Portland, Maine

A scenic day trip from Portland, with Casco Bay along for the ride.

By Mel Allen

May 27 2023


Aerial view of Mackerel Cove on Bailey Island.

Photo Credit : Alexey Stiop

You wake up in Portland to the cries of seagulls and the sounds of fishing boats and ferries along the waterfront. But just a short drive away, there await quiet peninsula roads with island views, a cliffside panorama out of a Winslow Homer painting, and a college town you won’t want to leave. Did I mention waterside lobster rolls and one of the most scenic souvenir shops anywhere? It’s a drive to remember—just trust your GPS to get you to all the stops you want to make. 

Start early to get in line for croissants at Standard Baking Co. on Portland’s waterfront. Then head northeast on Commercial Street, turn left onto Franklin Street, and—except for a brief stretch on I-295—you will spend the rest of the day driving country roads, windows down, breathing in the sea.

After about a dozen miles, pull in at 2 DeLorme Drive, the site of GPS tech giant Garmin and home of Eartha, the world’s largest rotating globe. The lobby is open to visitors, and you will be transfixed by seeing our planet looming in the three-story glass atrium, as if you are a tiny satellite passing by below.

Just north, turn onto Main Street in Freeport, where L.L. Bean’s sprawling campus and dozens of national outlets and local stores make it feel like an outdoor shopping potpourri. You will likely put a bag or two in the car. But less than five miles distant, Casco Bay beckons: Wolfe’s Neck Woods State Park is a gem with five miles of walking paths by the water, and ospreys and herons likely to be soaring overhead.

Another 10 miles brings you to Brunswick, home to Bowdoin College’s museums, beautiful campus, and a main street filled with shops, restaurants featuring cuisine from around the world, and a showstopper of a mural. You will be tempted to linger here, and the summer daylight is long, so do. But just ahead lies the Harpswell Peninsula, where villages and islands compose the town of Harpswell, giving it the longest coastline of any community in Maine.

From Brunswick, follow Route 1 for just a few moments, then turn onto Route 123 south to begin exploring this inviting peninsula. Routes 123 and 24 extend southward like tentacles, with Mountain Road connecting the two; water sparkles on both sides. Go slow. Cross scenic bridges, visit island villages, stroll trails that bring you to overlooks where Maine’s rocky coast is the star. One of the state’s most famous seafood restaurants, Cook’s Lobster & Ale House, is here on Bailey Island, with a jaw-dropper of a view. Explore the peninsula, and if lucky you will find yourself back at Eartha at dark, where it is lit like a moon, rotating ever so slowly, while Portland waits just down the road.

Scenic Coastal Maine Map
Scenic Coastal Maine Map
Photo Credit : Nate Padavick

Yankee‘s Favorite Places to Stop Along the Way

Standard Baking Co., Portland: In a city famous for culinary delights, this Old Port bakery in a vintage brick warehouse may be its most beloved. Simply one of the best in the country.

Eartha, Yarmouth: This 41-foot-diameter rotating globe was built as a signature attraction for DeLorme Maps, and when Garmin acquired the company it kept the lobby open and Eartha on its never-ending path.

Freeport: This pretty town turned shopping nirvana has more than its fair share of don’t-miss stops. Love craft beer? Maine Beer Company is one of the state’s best breweries, and yes, there’s a tasting room. Got a sweet tooth? Year after year, Wilbur’s of Maine Chocolates wins accolades for best in the state. And did we mention a certain Maine company built on a hunting boot?

Wolfe’s Neck Woods State Park, Freeport: Five miles of walking trails, including a wheelchair-accessible path, take you into a world of forest and marsh and sea, with island views and even famous paintings of seascapes posted along the way.

Brunswick: The tree-lined Bowdoin College campus inspired Hawthorne and Longfellow—and will no doubt inspire you, too. Its art museum holds more than 14,000 works, and its Peary-Macmillan Arctic Museum is an unexpected visit to another world. At 11 Pleasant St., just off Maine Street, don’t miss the Dance of Two Cultures mural, which grew out of a cultural exchange between Brunswick and Trinidad, Cuba. It is both a work of art and a testament to the merging of diverse cultures.

Cliff Trail, Harpswell: Behind the Harpswell town office on Mountain Road is a dog-friendly walking path along a tidal creek that takes you into a “fairy house” building zone, where all ages have constructed fanciful dwellings from twigs and bark. A more rugged cliff trail leads to spectacular views over Long Reach.

Salt Cod Café, Orr’s Island: Since 1845, people have stocked up on food and local goods at this site overlooking Harpswell Sound. The great-great-granddaughter of the original store owner will make you a lobster roll to eat beside the sea.

Cook’s Lobster & Ale House, Bailey Island: One of the most famous seafood landmarks in Maine, whose picture windows offer a one-of-a-kind view out to the famous Cribstone Bridge. 

Giant’s Stairs Trail, Harpswell: Discover one of the most memorable vistas of Casco Bay from this loop path, which takes you past rock formations sculpted by 500 million years of pounding surf.

Land’s End Gift Shop, Bailey Island: Route 24 ends here, with boulders to sit on while you watch seals. Family-owned since 1959, this shop is a tourist trap worth falling into.

Littlejohn Island Preserve, Yarmouth: The definition of “hidden gem,” this 23-acre property offers a 1.3-mile loop trail with views of islands shining in the near distance. Parking spots are few, but the short drive from Yarmouth to Cousins Island and then the causeway to Littlejohn is worth it by itself.