Fishermen try their luck off of Bug Light at the entrance to Portland Harbor. Photo by Joe Devenney

South Portland can be considered two-faced, but that’s actually a good thing. The city’s industrial face can seem foreboding, although it’s a far cry from the moonscape refinery ports of the Gulf Coast. But the less obvious face is quite welcoming to visiting boaters.

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When you arrive in South Portland, the most prominent structures are oil terminals and large petroleum tanks. In fact, South Portland boasts of being the second-busiest port for petroleum products on the East Coast.

Aerial Map

Thus, handsome Bug Light Park, home to beautiful flower gardens and a nice launch ramp, lies nestled between less-than-handsome oil-loading and -discharge facilities. (Note: a new petroleum-tank beautification project involving large-scale murals is slated to begin in May 2010.)

When approaching the harbor from the south, it’s easy to forget the steel and concrete of South Portland. This is especially true at Simonton Cove’s Willard Beach, a popular anchorage for local boaters. Located just off the big shipping channel at the southern entrance to Portland Harbor, Willard Beach has a soft, sandy elegance that few expect to find within a city. Other beaches south of this spot, among them Danford Cove, Maiden Cove and Ship Cove, can also be accessed by boat.

Boaters who intend to visit South Portland for a few hours can tie up for free at the Knightville floats at Thomas Knight Park…

Just north of Willard Cove is another notable “SoPo” landmark: Fort Preble, which guards the west side of the harbor mouth. From the sea, Portland Harbor looks a bit like an armed camp, and it was exactly that during World War II, the Great War, the Spanish American War, the Civil War and the War of 1812. Portland Harbor has always been considered a key shipping port and a strategic objective, a fact that was never lost on foreign and even domestic aggressors. Although they are now largely overgrown and aging semigracefully, huge granite or steel-and-concrete fortifications can still be seen pretty much wherever you look: on House Island in the channel fairway, on the Diamond Island Ledges farther up the channel and on the outer sentinels of Cushing, Peaks and Jewell Islands. Today the old forts add to the area’s charm.

Portland Harbor as seen from the Casco Bay Bridge. Photo by Joe Devenney

Fort Preble can be reached via the Spring Point Light Shoreway. Like Bug Light Park, the Shoreway encompasses a 1.5 miles of park greenery. As mentioned, Bug Light Park offers trailerboaters easy access to the harbor and Casco Bay via its big launch ramp with lots of parking. The park’s 9 acres of finely trimmed lawns, flower gardens and spectacular views look about as inviting as anything Fredrick Law Olmsted could have conjured up for bigger cities up and down the East Coast. But the park’s shoreside origins are anything but glamorous, as it was fashioned out of the combined sites of an abandoned lighthouse and a huge shipbuilding operation that contributed greatly to the Allied victory in World War II.

Although shipbuilding eventually became South Portland’s signature industry, the city started more modestly. Breaking away from the nearby town of Cape Elizabeth in 1895, South Portland originated as a largely residential community with small industries like the nineteenth-century chewing-gum factory that temporarily gave the city the dubious distinction of being “the world’s chewing-gum capital.” Various mills and smaller shipbuilding operations dominated the waterfront until the Liberty Ship expansion began in 1940.

Old fishing shacks are preserved as part of the waterfront park at Willard Beach on Simonton Cove. Photo by Joe Devenney

South Portland’s Liberty Ship Memorial represents the pride of the city. Not at all a grim reminder of the past, the open, cheerful memorial includes child-friendly exhibits and a playground. For history buffs there are also easy-to-read plaques and a self-guided tour honoring the 30,000 workers who turned out 236 of the ugly duckling ships between late 1940 and early 1945.

As you work your way southwest along the waterfront and into the Fore River estuary, the scenery varies between big, mostly empty shipping terminals and small, quiet riparian neighborhoods, complete with handsome Victorian-era homes. A marina here and a cluster of moored pleasure boats there indicate that South Portland is a city that caters to transient boaters. Spring Point Marina, tucked behind Spring Point, and Sunset Marina, just inside the mouth of the Fore River, are 2 of the 3 marinas in South Portland.

The third marina, South Port Marine, located near the Casco Bay Bridge, is a popular spot among transient boaters. Just be careful to stay inside the channel when getting to and from the marina. The narrow channel and the mud flats surrounding it are what give South Port Marine its reputation as the quietest marina in Portland Harbor. Moreover, both a huge shopping center and a convenient, old-fashioned, neighborhood-style shopping district are within easy walking distance of the marina.

Boaters who intend to visit South Portland for a few hours can tie up for free at the Knightville floats at Thomas Knight Park, on the other side of the Casco Bay Bridge. From Knight Park it’s an easy walk to the nearby shopping districts and restaurants.

Boaters in shallow-draft vessels can explore even further upstream into the Fore River’s Long Creek branch, which makes up the last trickle of the South Portland waterfront. Even with I-295 running parallel to the tidal creek, the scenery is almost bucolic. Blue herons, snowy egrets and osprey can be seen along the shore, which are lined by giant maples and oaks.

A view of the Portland skyline from Bug Light Park. Photo by Joe Devenney

Mill Creek Park's fountain and lily pads seem a world away from the South Portland waterfront. Photo by Joe Devenney

A windjammer and tour boat pass the lighthouse at Spring Point Ledge. Photo by Joe Devenney