In Maine’s Pontoon Capital, a Wet, Hot Lakeside Summer

Pontoon flotillas! Dance parties! Disco-themed booze cruises! The little town of Naples is one big party all season long — and nowhere else in Maine is quite like it.

By Jaed Coffin
Photographed by Mat Trogner
From our July 2023 issue

Many years ago, I fell asleep in the back seat of my father’s car while driving home to Brunswick after a trip to Vermont. Occasionally, I woke to groggy visions of pastoral New England: rolling fields, roadside farm stands, tired-looking general stores. Then, suddenly, we were stuck in a traffic jam, on the outskirts of a town I didn’t recognize. Rather than wait it out, my dad parked the car, and we went to have a look around. 

The source of the congestion was a bustling lakefront boardwalk packed with tourists. On either side of a swing bridge — the sort that rotates, rather than lifts, to let boats through — cars were lined up in both directions, and lines of kids had gathered by a railing to watch a double-decker paddle-wheel boat make its way through a narrow channel, live music drifting from onboard. Another traffic jam, of pontoon boats, formed nearby.

We ate lunch inside a huge white building, where crowds of people sat out front, in neon beachwear, sipping cocktails. Still coming to, I ordered my usual vacation cuisine: a side of onion rings. What arrived instead was a fried monstrosity called a “blooming onion,” roughly the size of my 8-year-old head. I felt like I was in Disney World. But the name of the town, it turned out, was Naples, and some three decades later, I finally made a point of spending some time there.

The boat queue approaching the Chute River, between Brandy Pond and Long Lake
The boat queue approaching the Chute River, between Brandy Pond and Long Lake.

About a half mile south of downtown Naples, a traveler passes by a preview of what’s to come, in the form of Moose Landing Marina, where a three-story, open-air hangar, maybe a couple of football fields long, is stacked full of motorboats. It looks a little like a Connect Four for giants, signaling fun on an almost military-industrial scale. A large sign reads: PONTOON CAPITAL. Across the street is the always-packed parking lot of the Umbrella Factory Supermarket, so named for the bright canopy of umbrellas hung upside down from the ceiling. There, mostly out-of-state pickup trucks fill their beds with 30-racks of cheap beer, barbeque supplies, and other summer essentials.

After that, it’s a short drive to the Causeway — the epicenter of that foggy childhood memory — across the Chute River, which separates Long Lake on one side of town from Brandy Pond on the other (it’s something of a point of local pride that the Chute, only 1,000 feet long, ranks among the shortest rivers in the world). Once on the Causeway, there’s no structure more conspicuous than the Naples Casino, its upper deck aglow in neon green lights. A good portion of the casino is occupied by Rick’s Cafe, and that, I recall, is where I had my first blooming onion.

On a busy Friday night, Rick’s looked just like I remembered it: almost everyone in beachwear, pink cocktails served in long-stemmed glasses, baskets of fried food. A summer breeze lifted the leaves of potted palm trees. Bailey Odum, the 27-year-old manager of Rick’s Cafe, wasn’t surprised to hear that my childhood memory of Naples had endured. When I asked her about the blooming onion, she laughed: “Oh yeah, we still have it. People are obsessed with it.” Those same people often ask Odum why this restaurant in rural Maine has palms out front. 

From left to right: The beach at Sebago Lake State Park; at the Causeway’s Harpoon Lagoon arcade.

From out in front of Rick’s Cafe, the full buffet of waterfront attractions, from aqua-trike and Jet Ski rentals to seaplane tours, is in view. I mentioned to Odum that Naples didn’t feel like any other Maine lake town I’d ever visited. At a glance, I said, the vacation culture of Naples gave off some Ozarks energy, at least based on what I’d gleaned from the eponymous Netflix series. “Yes, oh my god,” she said. “Exactly!” 

For years, Odum, who grew up a few miles away, in the sleepier lakeside town of Raymond, never understood what she calls the “funky flair” at Rick’s Cafe. Then, she took a trip to Florida with her former boss, Eddie Osborne, who owned Rick’s from the ’80s up until he passed away last year. Walking down Las Olas Boulevard, the central hub of Fort Lauderdale, it suddenly made sense to her. Tropical plants, vintage cars, Parrothead vibes — Osborne had brought a little bit of south Florida to rural Maine. “Look at this place,” Odum said, gesturing at all the campy memorabilia that fills the dining room. “We have a plane coming out of the wall!” 

The only other place in Maine that feels remotely like Naples is, I think, Old Orchard Beach, with its all-day-and-into-the-night boardwalk revelry. In Naples, there is similarly no shortage of entertainment. But it wasn’t always that way. Like many Maine lake towns, Naples was once a staid, stately resort destination. It had big old hotels that attracted well-heeled rusticators from Portland, Boston, New York. And Naples was uniquely connected to Portland via the Cumberland and Oxford Canal, which ran 47 miles over some 27 locks, transporting timber and farm products south and vacationers north.

Over time, the commercial balance shifted solidly toward tourism. In 1899, the Bay of Naples Inn opened, on the east shore of Long Lake, with 100 rooms and a staff of 85. Visitors arrived on steamships at the town landing, and then horse-drawn carriages whisked them to the inn. In 1902, the casino was constructed — a casino in an old sense of the word, as in a place for amusements but not, in this case, gambling. Over the years, it housed bowling alleys, movie theaters, dance and opera halls, and a roller rink. It served as a venue for local parties and political rallies. Famous entertainers, like Eddie Cantor and Rudy Vallée, made appearances. The casino’s inaugural act was Julian Eltinge, a renowned “female impersonator” who, after his Naples gig, went on to perform on Broadway and across Europe. 

Through the 1940s, the tourist economy stayed relatively stable. With the construction of U.S. Route 302, a car could start out on Forest Avenue, in Portland, and roll up to the Causeway without making a single turn. But by the 1950s, steamship service had ended and the complexion of the local economy started to change. The grand Bay of Naples Inn went out of business, and word has it that high-school kids used to party in the ornate, abandoned rooms until the inn was demolished, in 1964. 

From left to right: Boaters on Brandy Pond; a scenic floatplane flight takes off, from Naples Seaplane Adventures.

Housing previously reserved for hotel staff was converted into lakeside rental cottages. A Howard Johnson’s hotel, which opened in 1937 and operated until 1973, increasingly welcomed guests who enjoyed floatplane tours and zipping around on speedboats. The era of the genteel, tea-sipping, gown- and tux-wearing rusticator had clearly ended. The old cupola from the inn had been spared during demolition, and there was some local ambition to repurpose it as a historical monument. For years, though, it sat in limbo at a town-owned campground, where it was pressed into service as a mount for a basketball hoop and as a kiddie playhouse. In 2020, a local antiques dealer moved the cupola to his property, with plans to convert the beat-up structure into a one-bedroom Airbnb. Last fall, however, his property was listed for sale, for $2.5 million, unrestored cupola included. 

A few doors down from Rick’s Cafe, Chris Cooke opened Beacon Bar & Bistro two years ago, in a building that was previously home to, among other things, a gas station, a Chinese takeout, and a real-estate office. When I stopped by in the evening, customers were gathered around propane firepits, and Cooke made the rounds, chitchatting with his clientele. Born in Jamaica, he blends culinary traditions, from full lobster dinners to rice-and-bean bowls to hot-honey chicken sandwiches. But no matter their food order, patrons tend to wash down meals with colorful cocktails — lots of Jamaican rum and fruity mixers, like strawberry-guava.

“This is what our locals wanted,” Cooke told me, gesturing across the Causeway to Long Lake at dusk. “Good music, great food, and the sunset. It’s like you’re having dinner in your backyard,” he said. “But with somebody else making the meal.” 

Stream Reggae, probably Maine’s most prolific reggae band, was performing that night, and an all-ages dance party had developed on Cooke’s patio. “On their next set,” he told me, winking, “I’ll get up there.” Minutes later, he was at the mic, belting out a reggae classic, “Murder, She Wrote” (no relation to the cozy-mystery series set in Maine that shares the same title).

Clockwise from top left: the members of Motor Booty Affair — “Maine’s ultimate disco party band” — board the Songo River Queen II before a show; Motor Booty Affair fans; the Motor Booty Affair “lot scene” in downtown Naples; getting sweaty on the Songo River Queen II; aboard the Songo River Queen II (with a Neil Diamond tribute band Cherry Cherry).

A little later, the Songo River Queen II pulled into port at the end of its evening cruise, the Village People’s “YMCA” blasting from the decks, performed by disco-funk cover band Motor Booty Affair. Meant to resemble an old-time riverboat, the original Queen was launched in 1971, taking passengers on scenic trips around Long Lake, through the swing bridge, and into Brandy Pond, with forays into the Songo Locks that lead to Sebago Lake. Then, in 1981, someone flicked a smoldering cigarette butt into a trash can and the resulting fire destroyed the ship. 

The rebuilt Queen debuted a year later, almost a third longer than its predecessor (since the 2011 replacement of the swing bridge with a fixed bridge, the boat has been confined to Long Lake). As Motor Booty Affair wrapped up their encore, boozy passengers dressed in rainbow wigs and various other disco-hippie paraphernalia stumbled across the gangway and out onto the Causeway, then disappeared into the night. 

No Naples experience is complete without cruising Long Lake and Brandy Pond on a pontoon boat — the town has six marina businesses that rent, sell, and store boats. Naples has a year-round population of only about 4,000 but a summer population of more than 20,000, and some 14,000 boats call the town home, according to local officials.

As a newbie boater, I opted to rent from Dingley’s Wharf, mostly for the convenience of being able to park right on the Causeway and have a staffer from the marina tote our coolers and bags onto our 22-footer. After a brief boating-safety lecture, our family, with a group of friends, set off into Long Lake, toward the dozens of other pontoons floating in the distance. 

“These last couple years, we really saw the dynamic change,” said Shawn Hebert, the Naples Marine Safety Division harbormaster, who was sitting in his office, in a squat brick building on the village green. When so much was shut down around the country during the first summer of the pandemic, Naples saw an influx of first-time visitors. Many boat renters, Hebert told me, think boats operate just like cars, which leads to lots of “inexperienced traffic” and keeps Hebert’s crew extra busy responding to breakdowns and issuing citations for speed violations and disorderly conduct. 

Hebert sometimes imagines Naples as a combination of the busy outdoor-recreational scene in North Conway, New Hampshire, and the boisterous boardwalk scene in Old Orchard Beach. (Naples is, in fact, just about halfway between those two towns.) Members of his 16-person department can issue summonses on the water but lack authority to make arrests. For arrests, he has to call in state wardens. “Some people,” Hebert half-joked, sounding a little exasperated, “like to call us the mall cops of the water.” 

Clockwise from top left: Dancing at Beacon Bar and Bistro; Stream Reggae performing at the bar; Beacon owner Chris Cooke.

That afternoon, a steady wind had kicked up, and Long Lake was choppy. After a while, we puttered under the bridge and into the more sheltered waters of Brandy Pond (which, according to lore, was named for a barrel of booze that fell off a boat back in the 1800s). We wanted to check out an informal gathering place known as the Sandbar, and when we got there, we found a pack of at least 40 boats that had dropped anchor in a vast, bobbing circle. 

Chunky Dunky Ice Cream Boat
Wading with treats from the Chunky Dunky Ice Cream Boat.

College-age bros in American-flag swim trunks chucked a football back and forth while sipping White Claws. A few older couples kept an eye on their lapdogs that perched on nearby rafts. Moms carried travel mugs, presumably filled with something other than coffee, as they waded after toddlers held afloat by pool toys. The music of choice was country and classic rock, and there were more than a few flags flying astern with right-wing political messages.

People around town had described the Sandbar to me as “the Redneck Riviera,” “kind of Ozark,” and “very honky-tonk.” I might add “precarious.” With the wind still up, it was no small feat to slide our boat into a vacant slot and drop anchor without drifting into our new neighbors. Behind cans of Bud Light, they watched me maneuver. I thought they looked largely unimpressed. 

“Believe it or not, the Sandbar kind of manages itself,” Hebert told me. “Most of the frequent users, they know how special it is.” Boaters have an unspoken agreement with the adjacent property owners: keep things under control or lose the privilege. 

Suddenly, a clanky, electronic version of “Pop Goes the Weasel” drowned out the music playing from people’s radios — the Chunky Dunky Ice Cream boat was making its afternoon pass. The husband-and-wife duo of Barb and Richie Vieira has captained the ice-cream boat since the summer of 2020, when they sold their laundromat, 40 minutes away, and chose a semi-retirement gig on the water. The name comes from a term of endearment they told me friends had bestowed on their big-boned family. Their business slogan: “We’re not skinny dipping anymore! We’re chunky dunking!” 

Early on, the Vieiras worried that boaters and homeowners lounging on their docks wouldn’t want to be sold anything while trying to relax. “But 99 percent of the time,” Richie said, “people are happy to see us.” The Vieiras also had concerns about collisions, what with so many inexperienced boaters on the water, so they instituted a “we come to you” policy that involves a pool-skimming net on a 15-foot pole, for shuttling credit cards, cash, and SpongeBob popsicles between vessels kept at a safe distance from each other. “We haven’t lost one yet!” Barb said. 

Dockside pizza delivery from Randy’s Wooster St Pizza Shop.

We spent the rest of the afternoon yanking the kids around Brandy Pond on tubes and taking turns seeing who among the adults remembered how to water-ski. On our way back to the Causeway, we approached the old town landing, where, a century ago, genteel travelers stepped off steamships. Instead, an employee of Randy’s Wooster St Pizza met us there. She was waiting with several cheesy pies we’d called in for waterside pickup. 

While we were tied off at the landing, I started chatting with a group of tourists from out of state. I mentioned the Ozarks analogy to them. “No way!” one said. “I’m a Missouri guy, and this is way better than the Ozarks.”

April 2024, Down East Magazine

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