Issue: From the Chesapeake Bay Magazine Archives
Destination: Herring Bay

Deale, Md., and Herrington Harbour South lie at the opposite ends 
of Herring Bay, and of the cruising spectrum, yet both prove perennial 
favorites for cruisers for their ability to retain their charm without lifting a finger. 
[September 2013]

By Ann Levelle
Photographs by Vince Lupo

I wish I could say I enjoyed our boat ride to Herring Bay from Annapolis. After all, it was a nearly perfect June morning when my husband John, daughter Penny and I started out . . . cloudless blue skies, just enough breeze to cool the cockpit and little to nothing in the waves department. But, alas, Penny was in no mood to sit in the cockpit and enjoy the ride above decks, at least not if it meant being strapped into a hot and bulky lifejacket. So she and I spent the trip sweating it out down below, checking out the Albin 28’s nooks (which happen to be the perfect size for a two-year-old), coloring, reading books and . . . sweating. Did I mention sweating? Still, not a bad ride, but I could’ve used the above-water views.

Thankfully, by the time we arrived in Herring Bay—our destination for the rest of the weekend—even Penny’d had enough belowdecks time and was happy to get out in the fresh air. Our goal for the weekend was a simple one: escape from the house buying/ selling process in which we were currently entangled and introduce Penny to overnight cruising. Since she’d never spent the night afloat, we decided to go somewhere relatively close to home—in case of mutiny—and a spot where there would be plenty of fun things to see and places explore. We opted to spend the night at Herrington Harbour South, a resort marina that has a pool, a beach, watersports, a restaurant, playground and a lovely sprawling campus that could keep us occupied for hours just walking around looking at boats and wildlife. But first, wanting to also get a sense of the rest of Herring Bay, we had decided first to head to the town of Deale, at the north end of the bay. We would quickly learn that Deale pretty much is the rest of Herring Bay, but I’m getting ahead of myself.

As we neared the red “2” at the southern edge of Long Bar, John called for Penny and me to come up, so we could have a look. This is the “safe” way in. Even if you’re headed for the north end of Herring Bay, unless you want to run the risk of tripping on Long Bar (which gives you as little as three feet of water in some places), you need to come pretty much all the way to the south end, the aforementioned “2”, right outside the entrance to Herrington Harbour South, and then head north. It’s not a terribly long diversion, and it has the benefit of taking you past some lovely homes along the shore of Herring Bay. And soon we found ourselves part of the busy weekend parade of boats entering and leaving Rockhold Creek. Before we were fully in the creek, though, we began to get an idea of what Deale is all about: boats. Off to port, all but filling the mouth of Tracys Creek, was Herrington Harbour North. This is the 600-slip twin to Herrington Harbour South. It has all the amenities of its southern sister—pool, a waterfront restaurant, fitness center, wi-fi, lounge, etc., but also a West Marine store and an enormous boatyard with every sort of marine contractor you could think of based on site. And that was just the beginning of the living boat show that dominates Deale. Next we passed Shipwright Harbor, Rockhold Creek Marina, Paradise Marina, countless private docks, and a hefty charter fishing fleet at the docks at Happy Harbor Restaurant before deciding to double back to Skipper’s Pier and stop for lunch. As we headed south again, I took more notice of the landscape, instead of just boat watching, and admired the tiny cottages lining the creek, nearly every one having its own dock and runabout or big boat. There were a scant few larger, upgraded homes, but the majority seemed to still be of their humble cottage beginnings—-unchanged, save an added dormer here or there, an upgraded pier or boathouse added over the years.

In the next few weeks, I would make a few more trips to Deale to fi nd out what life was really like in town. With a population of around 5,000, the town likely has a close ratio of people to boats—3 to 1, I’d guess—but it’s pretty evident that many of the boat’s owners are from out of town. Brian Buck of Columbia, Md., whom I’d met at Happy Harbor on a gorgeous Saturday afternoon, has been keeping his boat here for 25 years. “I come down here for the peace and quiet,” he told me as he enjoyed a beer and burger on the restaurant deck, which looks out on Rockhold Creek just below the Deale Road bridge. Deale, he says, is “the last vestige of civilization in Maryland”—a quiet town that’s just 30 miles from the chaos of D.C., but which still has echoes of life fifty years ago.

Also at Happy Harbor that day were Bill Ogilvie and Lisa Cheakalos, who both live in Deale and who had tied up for lunch after a morning jaunt up and down the creek. They both agreed that things here have a habit of staying the same, and that the locals have a lot to do with that. As a for-instance they told me about Safeway’s attempt to open a store here in the early 2000s, and how the whole community went nuts—putting up “Stop the Sprawl” signs and ultimately quashing all efforts to bring in the big chain. And, oh yes, they said, who could forget the uproar when there was a proposed stoplight a few blocks from the water at the intersection of routes 256 and 258? Again, the community fought tooth and nail against it, eventually getting a traffic circle instead.

After visiting Deale on several weekend days, my friend Beth and I decided to do a fi eld trip to see what weekday life was like here. After visiting a few consignment/antique shops in town (which, by the way, really doesn’t have anything resembling a main street or town center), it was clear that the water really is the town’s focal point. Out on Deale Road or Rockhold Creek Road or Deale Churchton Road, we didn’t feellike we were there. And we didn’t feel like we were there until we’d settled in for lunch at Happy Harbor. After we’d been there for a while, looking out on the water and chatting aimlessly with locals who clearly spend most of their days right there, playing cards on the porch, sitting at the bar nursing a beer. Clearly, we agreed, this is one of those places where you have to be on or near the water to be there.

Meanwhile, back on the Levelle family vacation, we idled back down Rockhold creek, merging into the southbound lane of the two-way traffi c on the creek—charter fi shing boats returning from their morning charter runs, skiffs puttering the creek, small powerboats loaded with rafts and wakeboarding equipment, and sailboats heading out for an afternoon on the open water. Having reached Skipper’s Pier, we exited the Rockhold Highway and spun around into one of the restaurant’s slips. Thankfully the wind that had whipped up out of the north didn’t sway our docking too much, and Penny did a surprisingly good job playing below while we adjusted lines. We were soon seated at a table on the on restaurant’s patio under colorful umbrellas, noshing on calamari, then filling up on a steak-topped salad, fi sh and chips (and mac ‘n’ cheese, of course). We also enjoyed some excellent boat- and people-watching, which happens to be especially fun here at Skipper’s, where the creek views are relatively unobstructed to the south. To the north a pier extends from the restaurant out to a two-story dock bar area (yes, with a with giant parrot) and a steady crowd of patrons, many of the Harley Davidson persuasion—and, as you might expect, their cousins the go-fast boaters. But we couldn’t hang out and watch forever, as it was nearing Penny’s naptime and we still needed to reach our slip for the night.

Now it was time to head south, to the newer, resortier side of Herring Bay. The trip out of the creek and to the marina only took but 20 minutes or so, and before I knew it, we were on Herring Bay’s other two-lane boat highway— the one into Herrington Harbour South. Heading into the cut leading to the marina feels reminiscent of cruising in Florida to me. But instead of spitting us out into a claustrophobic mangrove-lined grove, the cut deposited us into a wide-open basin of boats, with docks leading out from every edge. Though boats pop out from nearly all 360 degrees of this basin, the shoreline is filled in with lush native vegetation—a point of pride for the marina and its owner Steuart Chaney.

I wouldn’t discover this until later, but my old-school north, new-school south theory was a bit flawed—because Herrington Harbour South resort has a long history of its own. Before Chaney bought the property, in 1977, it was called Rose Haven (after founder Joe Rose) and comprised a bingo parlor, snack parlor and arcade along the beachfront, as well as a bathhouse, and Rose’s Musical Bar, complete with somewhat illegal slot machines. The icing on the cake was a dilapidated cinder block motel and a yacht club, complete with faux lighthouse on top. The latter two buildings still stand today, but a time traveler from the 1970s woudn’t recognize them. Over the years the Chaneys have transformed the place into one of the Bay’s top boating resorts. The Chaneys have not only added amenities, but also gone above and beyond in making the marina ecologically friendly by eliminating bulkheads, planting native marsh and grasses and a host of other upgrades. The Herrington marinas were named Maryland’s 2011 Clean Marina of the Year.

We were met on B dock by a very helpful young dockhand, who helped John make short work of docking just in front of a rather large yacht that just so happened to be holding a wedding ceremony on board that very moment. You know, everyone’s favorite no-pressure docking situation. . . Luckily no docking horror story came from it. Indeed some of the wedding guests and at least one member of the wedding party waved at us as we one floated by and tied up. John followed the dockhand up to the marina office to check in, while I tackled the herculean task of trying to convince Penny to nap. After an hour of negotiations, I gave up; she was just too revved up about the beach. Okay, plan B: don our bathing suits and head for the beach. Along the way we wandered past the very crowded pool (it was, after all, the first warm weekend of summer) a small playground, then through the lovely manicured grounds at the hotel, and finally reached the beach. We found a few empty lounge chairs under one of the thatch umbrellas and quickly dropped our stuff so we could go get our feet wet. By the time we reached the water, Penny was in seventh heaven. A little afraid of the water still, she had ample room to play in the sand and shallow water behind several small rock breakwaters without worrying much about any wave action. And when we did bring her out into deeper water, we were able to wade out quite a ways without the water getting above her shoulders. While we were playing, wading and digging in the sand, other beachgoers were busy playing football and sunbathing, and more were steadily streaming in and out of the water on kayaks, stand-up paddleboards and even a paddleboat.

On our way back to the boat we walked all the way down the beach toward the marina’s long rock jetty, where we saw a masseuse setting up her table for a waterfront massage, and yet another wedding party (they do a lot of weddings here) this one apparently prepping for their ceremony at the outdoor venue facing the beach. After a quick stop at the boat for shower gear, we traipsed across the marina’s campus to the private showers to get cleaned up for dinner.

As we headed back from showers, it all suddenly seemed very beachy—feeling the heat of a slight sunburn on my skin, seeing people carrying beach bags and water toys, smelling the salt air, hearing a steel drum band playing outside at Mango’s, the resort’s restaurant. I truly felt like I was on an island vacation . . . and hearing it would be a 45-minute wait for a table at Mangos, well, that just made it seem all the more real. Not that we should have been surprised; after all, we showed up at 6 o’clock on a Saturday evening, at a busy marina, at the only real sit-down restaurant within miles.

But with a toddler in tow, you can’t roll with the punches quite as gracefully, which is to say we couldn’t just go relax at the bar, as we would’ve done in our pre-kid days. So another plan B was in order; we headed to Honey’s Harvest, the little convenience market and deli just across the street from the marina’s main building. And while we may not have had a waterfront view or a steel drum band playing in the background, we still had a delightful little meal. The deli caters to boaters, offering simple foods—sandwiches and such—throughout the day, and fun specials on the weekend, like “pizza Fridays” and “slider Saturdays.” And I can personally attest to the slider’s deliciousness, and that the place makes a mean milkshake.

Full and happy, the three of us meandered back to the boat. After managing to get Penny to bed, John and I were able to relax in the cockpit and enjoy a little more Caribbean music coming from Mango’s. But soon after, as the wedding reception on the other side of the marina slipped into high gear, the music changed from island-mellow to thumping-dance-hits-of-the 80s. In fact, there was a surprising amount of activity going on—-the outdoor reception across the way, an indoor reception at the big hall near the marina office, an outdoor movie playing on the beach, a band at Mango’s, and people heading every which direction along the docks. Yet we were alone in the middle of it all, still able to enjoy a quiet evening to ourselves, even if the background noise was the Village People singing “YMCA,” instead of crickets chirping and frogs croaking.

The next morning we woke early, courtesy of our excited little boater (gee, what a surprise), who was ready for action not long after sunrise. With nothing much to do pre-seven a.m., we played on the boat and cleaned up for our journey home, then made our way back to Honey’s Harvest for breakfast, where we fueled up for the day with coffee, breakfast sandwiches and a few provisions for the trip home. Then we took a little walk around the docks, spotting some ducks and herons, a few frogs in the reeds and lots of dogs out for their morning strolls. Penny seemed less than enthusiastic about another visit to the beach, so we decided to depart early, hoping to make it back to Annapolis by lunchtime. Following seas all the way made for a wild and surfy ride, so I couldn’t stay belowdecks for long, at least not if I wanted to keep my breakfast. So after a half an hour or so of claustrophobic rock and roll, I went above for an anti-nausea breather. And that was all it took (who knew?) for Penny to fall fast asleep in the quarter berth—leaving me to enjoy the ride and the breeze topsides.

We pulled into the boating club around 11:30 that morning, completing a successful weekend trip if there ever was one. In fact, it was so successful that we had to practically tear Penny from the boat, howling at the top of her lungs the whole way down the dock that she wanted to go back to “her” boat. Granted, it could have been because we had to wake her up from a nice nap, but I prefer to think of it as her inner boater coming out to greet us. Either way, the trip was a success— we’d introduced Penny to proper cruising, enjoyed some good meals and gotten to know the old- and new-old school sides of Herring Bay.