Issue: From the Chesapeake Bay Magazine Archives
Destination: Hooper Island, MD

Sailing the middle bay
Two old friends reunite for a downwind 
sailing cruise on the middle Bay. What 
more could a girl ask for? Wind, wine, 
crab imperial? Perfect. [May 2010]

By Jane Meneely
Photographs by John Bildahl

There we were, the tallest thing on Hooper Island, and lightning was ripping through the sky like a giant zipper. Not that we were going anywhere. We were humped up, high and dry, atop a muddy flat just shy of the Barren Island Gap channel into Fishing Creek. Don't ask how we got there. That part doesn't matter. What does matter was that our mast was rearing up into the swirling storm like a giant finger. A giant middle finger. Yes, my normally docile little Petrel was egging on that storm, no better than a street urchin who's just scrambled over a very high fence, leaving a portly and breathless cop behind. The gods take a dim view of such taunts, and as they readied their thunderbolts, Karen and I desperately tried to figure out how not to get fried. It hadall started innocently enough. My brief little e-mail out: Hey, ya wanna go sailing for a week in July? Her brief little e-mail back: Sure.
It was that easy.

Karen and I met in fifth grade, bonded in seventh, were all but joined at the hip during high school. And, though we've gone our separate ways long since, we've remained spiritually conjoined in the way of longtime friends. She's the stylish quiet blonde; I'm the frowsy frizzy-haired talker. I finish her sentences; she keeps my secrets. Once upon a time I had a little sailing dinghy, and I took Karen sailing--her first time ever. We were 12 years old maybe. We ate Little Debbie cakes and swam off the wooded bluff that is now Bert Jabin's Yacht Yard on Back Creek in Annapolis. Eventually Karen became the captain, and we took the Annapolis Yacht Club championship the year we graduated high school, beating the pants off everyone else all summer long. (Go ahead. Look it up. 1970.) We've been raising hell and lowering expectations for years. We didn't marry princes, though we sure thought we had. We didn't get the castle, but the location of the house was good. And now we brood over empty nests and wonder how twenty--make that thirty--years can go by so fast.

Our plan for the trip started big but quickly got whittled down to four full days, sandwiched between Karen's business appointments. Still, four mid-week days on the Bay is nothing to complain about. Bubba, my once-moody and recalcitrant Atomic 4, had been behaving beautifully all summer long. Turn the key and off she'd go--out and back again. Grateful, I'd finished spiffing up the topsides, redone the nonskid, painted the cabin interior (again), hauled out and gotten the bottom done (and the centerboard loose). Petrel looked like a million dollars (except for the teak; Paul hadn't gotten around to that), and she was ready to step out and cover some territory.

Karen arrived at Shipwright Harbor on the late end of Monday and lugged her gear to the boat. I had brought along my laptop, my guitar and a large leather purse into which I'd crammed a toothbrush, a few pairs of knickers, a bathing suit, a long-sleeved shirt, a T-shirt and a pair of shorts--paint-splattered shorts at that. Karen, by contrast, had so much stuff I was surprised it had fit in her car. One bag held a camp stove--for making espresso, she said. There was a bag of food--in case I hadn't brought enough. There was her duffel of clothes--Karen likes clothes. There was a duffel of bedding. She pulled out a box of wine--a good sturdy red. Karen was loaded for bear. You never know when a bear's going to come at you, and it's good to be ready. I love that about Karen. Bears do too.

After a brief bit of catching up, we crashed, only to awake in the morning to a sky heavy with gray clouds and the threat of rain. The forecast for the whole week was like that: unsettled weather, NOAA called it, with the possibility of severe 'storms in isolated pockets throughout the Bay area.

Sailing the chesapeake bay Even so, a lovely breeze swept in from the northwest, a perfect angle to head across the Bay. So we ignored the grim skies and motored out of Rockhold Creek, hauled up the sails and cut loose for the mouth of the Choptank River. No sooner did we clear the confines of Herring Bay but the sun burst through, the clouds scattered and the sun strode forth to dazzle the wave tops. The world sparkled. Petrel danced. Life was good.

We pulled out the chart book and reviewed our options. We could round Blackwalnut Point and sail up to Tilghman. We could reach all the way to Cambridge and probably not even tack. We could. . . .
    Karen took the chart and looked at it critically. What about the Little Choptank? she asked. (Karen wanted to duck into a place she hadn't been to.)
    We could go there too, of course. It would be dead downwind and hot. It would be a long frigging sail. My idea of a good sailing vacation is going where the wind wants to take you, and the fewer the tacks the better.
    Maybe the wind will shift, Karen said.
    Maybe it would. I relented.

We reached across the Bay, straight toward Sharps Island Light. And the wind held. Every time we tried to cock the boat south, we'd be rocking and rolling, sails flapping in the hot air. Dead downwind is a fast enough point of sail, but because you're moving with the wind, it doesn't feel like it. And on a hot sunny downwind day, a body just swelters there in the cockpit. So we would crank her back to a reach and edge closer to the Choptank shore. Finally we just tacked back to the west, figuring to drop south some, tack around and reach again for the Little Choptank.

Our reach west didn't help much, and nothing would do but that we point ourselves downwind, straight into the river, and hope for the best. Turning on the engine helped. Bubba had us up Brooks Creek before the sun went down.

We anchored off a secluded shore, broke out some cheese and crackers and sipped on that good red. Karen's face was aglow with the sunset. She's an avid kayaker, and kayaks would have made this the nearside of heaven. But we needed another 10 feet of boat to haul kayaks around. No matter, said Karen. A little more wine and nobody would care about kayaks anyway. The breeze brushed the top of the water with a gentle hand. It didn't actually get chilly, but it sure was pleasant. And there seemed to be a lot of wine. In fact, there was so much wine that neither of us noticed that the sun shower Karen had laid out on the cabin top in the heat of the day, had slowly leaked away so there was no water left. Karen lifted it up and gave it a puzzled look. Maybe we'd taken a shower and just couldn't remember? She looked at the deck underneath it, as if she might see a lovely reservoir of warm water there just waiting for her plunge. No. She sipped a little more wine. I sipped a little more wine. We weren't the least bit smelly, I pointed out. At least I wasn't, and I didn't care if she was. Have some blueberries, Karen said.
    Blueberries? Wine would be a serving of fruit, wouldn't it?
    A sherving of flute? Karen said.

We must have gone to sleep, because suddenly it was morning and a glorious one at that. The wind had kited around so that it was coming from the south. We could sail all the way to Havre de Grace! I said. But noooooo. Karen wanted to go souther still. Back across to Solomons maybe, and up the Patuxent. Or maybe stay on this side and down to Hooper Island.

    Hooper Island? The wind would be on the nose, I said.
    Well, let's get going then, she said, this could take a while.

Karen is my best friend in the whole world, and I would do anything for her. But I had to fight her on this one. I reminded her that a nice sailing vacation implied a lot of easy reaching from point A to point B, especially on a hot July day when the wind is sure to crap out around noon.

Nonsense, said Karen. She'd been on this Bay a time or two, and she saw nothing wrong with nice easy reaches back and forth across the wide expanse of Bay as we inched south ever so slightly with each tack until finally we got to someplace she'd never been before. Karen never raises her voice, at least not so you'd notice. But she does have a stubborn streak, and she had the tiller, and Petrel was pointing resolutely south, or would be once we rounded out of the Little Choptank.

    Okay, I said. But let's make it an adventure.
Karen's left eyebrow went up like a raised scimitar. She'd been on my "adventures" before. No way, she said.
    Way, I said, and pointed to James Island on the chart. I think we can cut between James Island and Oyster Cove.
    No way, she said, pointing to the skinny numbers.

    I bet we can do it and not see less than four feet, I said. And if we make it through, we'll have saved a huge amount of distance and might be able to lay a course for Cove Point and Solomons.
    Karen's scimitar wavered a bit.
    I'll even turn on the depthsounder, I said, uncleating the centerboard line and letting it drop. If we touch, we'll crank her up, go about and be outta there.

She relented. The breeze eased us gently along, pointing us perfectly for the center of the gap between the island and the shoreline of Taylors Island. And I was right. Nothing less than four feet the whole way. Except maybe that little bit where all the crab pots were and we kinda scraped a little. Nothing to text home about. And we pretty much had to tack just about then anyway. . . .

When we cleared James Island, we were heading nearly due west on a close haul across the Bay, aiming well above Cove Point. Karen started tinkering with the boat. Let's loosen the topping lift, she said. Let's tighten up the jib halyard, she said. Let's see if we can't get that jib sheet in more, she said. And how 'bout we change those fairleads.

But she didn't really mean "we." She was having a grand time, hanging on to the tiller like it was a wallet and "noticing" things about the boat that really didn't need noticing just then. But with each little tweak I could feel Petrel stretch her legs, move out of her groggy early morning stupor and start to step it up. This is how we beat everyone during that magical summer so long ago. And it was pleasant sailing across the Bay, all across the Bay, the whole long way across the Bay, and then tacking around and sailing all the way back and being not that much farther south, really, than we'd been just an hour before. 
    This is great! Karen said.

After about six hours of this we were in a position to make a choice: Solomons or Hooper Island. I was all for Solomons. It was smack in front of us. We could round up into Mill Creek or pull into a marina. . . .
    Hooper Island looks interesting, Karen said.
    Okay, I said. But let's make it an adventure.
    Out came the scimitar.

Really, I said. I bet we can follow the Barren Island Gap into Fishing Creek. The shallowest spot on the chart is three feet. Petrel draws less than that with the board up. What could go wrong?
    Karen was sharpening the blade.
    Really, I said. We sail straight east, which we have to do anyway. We pick up the Barren Island marks. The worst thing that can happen is we bounce in the shoal spot, have to tack out and go all the way south around Applegarth. If we make it in, though, we save gobs of time, and we can walk to Old Salty's for dinner.

The lure of dinner ashore did the trick. And we made it across the Barren Island flats without a hitch. Bubba ran like a champ. We were within spitting distance of Upper Hooper Island, well within sight of the Fishing Creek bridge, but there was something wrong with the picture.

    The public wharf is on the mainland, right at the foot of the bridge, I said.
    I just see a lot of marsh grass, Karen said.
    Me too, I said. And then I did something that always gets me into trouble. I started to speculate. Maybe Isabel took out the wharf, I said. Isabel wreaked holy havoc on Hooper Island. Maybe they moved the landing over there, I said, pointing to a manmade basin filled with workboats that sat on the island side of the bridge. There looked like a narrow cut in the marsh grass that would lead us in. I turned Petrel out of the channel and--whumpo thunko--we bought a little chunk o' Hooper Island waterfront right then and there.

Of course the tide was going out, and quickly. I jumped overboard and tried to push Petrel back to the deep side, but nothing doing. Karen handed me the anchor. March, she said. So I marched. But kedging did nothing but get us pointed in a slightly better direction.

    So much for dinner ashore, Karen growled.
    Tut tut, I said. You underestimate the hospitality of these people. One of those workboats will pull us off, just you wait and see.
    Three workboats streamed past.
    So much for dinner ashore, Karen growled again.
    Tut tut, I said, picking up my cell phone.
    A woman named Tracey answered the phone at Old Salty's.
    We were going to come for dinner, I told her, but we're kinda stuck.
    You need a ride?
    Sorta, I said, and I explained our situation.
    I'll call my dad, Tracey said. You just sit tight.

In no time Jimmy Simmons pulled up alongside in his workboat. I can't pull you off, he said. You're going to have to set here till the tide changes. High tide'll be along around 2:30 this morning. But I'll take you in to Old Salty's and bring you back again. Karen and I thought that was pretty sporting.

Once he had us back in the channel we could see the public wharf, right where it's always been, hidden behind the marsh grass. Look at that, I said. And look at the way the channel leads right inside the basin where the workboats are.

Bay sailing map Jimmy Simmons was shaking his head. I dunno what you were thinking, he said, looking quizzically at Petrel, now leaning a little on the mud.
    I didn't know either.

Karen raved about the crab imperial at Old Salty's. I thought the vodka tonics were pretty easy on the tongue. In any event, we polished off dinner and divvied up a slab of lemon meringue pie before we walked back to where Jimmy Simmons waited at the dock. (Tracey, by the way, got a hefty tip.)

Jimmy was able to get us right up next to Petrel, and despite the extreme angle, we were able to climb aboard. Karen turned in and I hunkered down in the cockpit and played my guitar for a while, entertaining the seagulls. Finally I climbed down below and fell asleep too.

The thunder woke us up. Rain poured down in thick sheets, and lightning bounced around the horizon. We scrambled into our foulies and hustled up on deck. Petrel was actually afloat, though just barely, and Bubba started up at first crank. We had to get out of there before the tide started rolling out again--and before lightning reengineered our masthead light--so we hauled up the anchor and chugged out the channel. By the time we cleared Barren Island, the rain had slackened and the lightning had moved south. The wind blew fresh from the southeast. It was 5:30 in the morning, and the soggy dawn was dim in the sky.

Up went the sails. Why not? And Petrel sailed briskly north, toward the mouth of the Choptank. We're going to Tilghman, I said.
    I'm going to make espresso, Karen said. She rummaged around down below and emerged in the companionway with her camp stove and little espresso pot. Carefully she measured ground coffee into the nest. The secret to good espresso, she said, is to pack the coffee down hard. Which she did.
    Nonsense, I said. The secret to good espresso is cream, and I dug into the cooler for the half-pint I knew was  buried under the ice.
    Only if the cream is hot, Karen said.

Karen is the type of person who follows recipes, and whatever she makes  tastes wonderful. I never follow recipes, and whatever I make lands somewhere on a scale of one to ten, give or take. If Karen ever offers to make anything for you, you just want to sit back and let her go for it. So I steered the boat while Karen boiled and stirred and ultimately poured a hot steaming elixir into a pair of tin cups. We still wore our foulies. The sky was still grim. But the wind was sweet and dry, and we sipped on Karen's wondrous brew and glided up the Bay in the wee morning hours as the storm grumped off toward the Atlantic. Supercharged with caffeine, we completely ignored the fact that we'd gotten up at an ungodly hour and now were committed to a day's sail back to the Choptank River. In fact, we made great time, and it was delightful to reach 'Tilghman with plenty of daylight to spare.

Dogwood Harbor is the public wharf on the Choptank River side of Tilghman, just above Avalon Island. Avalon Island is now the home of the swanky private club for the swanky private Tilghman-on-Chesapeake development (but they do accept transients). The Tilghman-on-Chesapeake clubhouse is lovely, but we passed it by and tucked into the public wharf. The landing there is for loading and unloading only. This is where the crabbers come to drop off their bushels. Here too is where a pair of skipjacks are moored. The Thomas W. Clyde is being substantially rebuilt to get her ready for the dredging season. In front of her sits the Rebecca T. Ruark, the oldest of the skipjack fleet still in action (technically she's an oyster sloop, but let's not split hairs). Captain Wadey Murphy was just dropping off a passel of passengers when we pulled up to the bulkhead in front of him. We weren't in his way, he said, so we made Petrel fast and scrambled ashore. Photographer John Bildahl was waiting for us, and he wanted to introduce us to artist Bill Cummings [see "Just One of the Boys," June 2008].

I'd heard about Bill Cummings. He'd been a bridge tender for a while, working the Knapps Narrows Bridge. And he was bored sometimes, when there were no boats coming through. He'd always wanted to paint, so he decided to start painting the view from the bridge. He painted that same picture over and over and over again, in all weather and all seasons. When he finished a painting he'd give it away. He got pretty good at it, and there are paintings of that scene stashed all over Tilghman Island. Now he paints other scenes, often from his memories of childhood on the island, and they sell for as much as $2,000 apiece--and that's only when he'll part with one.

Cummings, now in his early 80s, was only too happy to show Karen and me his studio and chat a bit about his subject matter--the Tilghman he remembers from when he was a kid and the work he did as a young man, hauling nets and generally staying busy on the water. After a pleasant visit we ambled on, stopping to buy snow cones from Chrissy Thomas, the red-haired proprietor of Chrissy's Cool Sno-Balls who had set up shop in the wide open door of her father's automotive shop. I got the blue flavor, Karen chose the red, and thus fortified, we turned back to Dogwood Harbor, where Captain Murphy awaited aboard the Rebecca T. Ruark. He had invited us along on his six o'clock sail.

As luck would have it, his six o'clock group was a no show, and though Captain Murphy offered to take us sailing anyway, we demurred, promising to come back another time. It seemed a shame to make him fire up his push boat for just the two of us. Instead we chatted about skipjacks and Tilghman and oyster dredging and . . . Ol' Captain Wadey Murphy's got more stories than a New York cabbie. We could have stayed there all night, but our bellies got the best of us. Our sugar high had worn off, so we strolled down to the Tilghman Island Inn for some serious food.

Tilghman Island has great places to eat: Bay Hundred, the Bridge, Harrison's Chesapeake House, Tilghman Island Inn and a wonderful little cafe, Two If By Sea, which sits conveniently next door to Crawford's Nautical Books (which is often inconveniently closed except on weekends; drat). Karen and I decided to put on the dog and go gourmet. She'd been talking nonstop (or as nonstop as Karen ever talks) about that crab imperial at Old Salty's. Don't get me wrong, I think Old Salty's has terrific crab imperial, but I was just tired of hearing about it. I figured the Tilghman Island Inn, which is known for its inventive menu, local seafood and regional favorites expertly prepared and beautifully served (I know it sounds like I'm quoting off a brochure here, but I'm not), would quickly shut her up.
    Here, I said. Eat this.

Karen had a plate of crabcakes in front of her and eat them she did. Not a peep about crab imperial. Meanwhile I tucked into a plate of Choptank Sweets fresh from the Choptank Oyster Company, an aquaculture operation near Cambridge. I'm fully in support of an industry that provides me with fresh oysters in August.

We decided to stay put in Dogwood Harbor, even though overnighting there is strictly verboten. It was so late by the time we'd finished our, um, loading and unloading, that it would have been foolish to move. Our evening was uneventful and a bit still. Only the barest whisp of wind found us there at the dock. And then all hell broke loose. Thunder, lightning, rain. At least that's what Karen said. But I was dead to the world. Probably a good thing we weren't at anchor.

The next morning we legged it down to Two If By Sea for breakfast and got back to the boat just as John Madert, a friendly official from Talbot County, was fastening a warning ticket to Petrel's stanchion. We assured him we were just leaving, and about two hours later--after chatting with him about this, that and life in general--we finally started freeing our lines. That's when the Swiss family showed up, having just missed the Rebecca T. Ruark's morning sail. They were heartily disappointed, and, well, one thing led to another, and soon they were all happily ensconced in Petrel's cockpit as Karen and I extolled the virtues of the cruising life.

We didn't leave in earnest till noon. And then Bubba refused to start, so we had to sail off the dock--and worse, beat our way around Blackwalnut Point, which took us till cocktail hour. Fortunately we had a lovely breeze and a short sail across the Bay to Rockhold Creek and home. Outside the Deale jetties, Bubba miraculously started up on the first try, which meant we were actually back at the dock before dark.

Whew. Our trip was over. Bubba only misbehaved that one time, and really, if he had started up on Tilghman we would have motored through the Narrows and been home much too soon, so all's well that ends well. Four days on the water, four days on my own little sailboat, four days with my best buddy--it was perfect, just perfect!