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Overnight options on the Chesapeake

Selecting one of my 10 favorite overnight/weekend destinations on Chesapeake Bay within a daysail of Annapolis depends partly upon my mood and whether I want to be around people on land. Being with boaters on boats is different because fellow sailors afloat aren’t exactly people afoot on the hard, although I’m not sure I know what I mean by that.

Once the mood is determined, the next thing to factor in before departing is the wind direction. With a brisk northerly, I head south; a brisk southerly, I go north. Homeward bound, wind means nothing because my destination is fixed anyway.

A daysail across the Chesapeake to the Eastern Shore and the mouth of Eastern Bay can take me to the Miles River, around Rich Neck, and to the tiny village of Claiborne on Tilghman Island — about a 23-mile cruise. To mingle with crowds, I would continue on for another five miles to the charming, but crowded and touristy town of St. Michaels — which has good restaurants, lively pubs, and a first-rate maritime museum.

Claiborne has a few folks strolling about idly and a post office, but little else. The cramped, picturesque harbor on Tilghman Creek is enchanting and lost in time, with a free county dock where you may find space if the crabbers haven’t already taken it over with their workboats.

If I’m towing my dinghy, I can anchor off, row in, and tie up to a tree on shore. Within walking distance lives an old friend, the colorful and somewhat eccentric Ruth Noble (Baba) Groom, a socially active hostess devoted to her animals and entertaining. She lives in the big main house at Mineral Springs Farm, where she looks after many horses, dogs and cats. There are two guest houses and a freshwater pool with an outdoor shower. She may or may not have a spare room available, but that’s no matter because I prefer sleeping on my boat anyway.

The Wye River

Just across from Claiborne on the other side of the Miles is another favorite: the Wye River, made up of three branches: the Wye East (“Front Wye”), the (“Back”) Wye, and the Wye Narrows. Shaw Bay is the major anchorage and raft-up area and beyond are a half-dozen or so creeks and coves, nearly all of them picture-perfect anchorages.

There are no fuel docks, but Wye Landing is busy because of its public launching ramp and activities relating to crabbing. The road leading to the landing fills early in the pre-dawn for miles with cars and boat trailers from afar. The river is famous for producing some of the largest crabs on the Bay.

Schnaitman’s Store and Bait Shop is an old established family enterprise where sandwiches are sold, and commercial crabbers unload their live catches in baskets to truckers heading off to market and restaurants. Try and get an invitation to visit the supply shed, which has a cold keg of tapped beer in a barrel of ice. Here the regulars — good old boys in tractor caps, bibbed dungarees and boots — sit around in battered chairs and on benches, bantering with one another in strange dialects and ogling girlie calendars.

Rowboat rentals also attract “chicken neckers,” amateur crabbers who prefer chicken parts as bait and set out a “trot” line to “dip” crabs with nets. Catches can be steamed, seasoned and eaten at picnic tables.

That’s the people part of the Wye, but getting away from people (if not boats) is easy. Just pick a creek and drop the hook. One of the most popular is Dividing Creek, but one creek is as pleasant as another. The largest raft-ups, of which there are many, form in protected Shaw Bay just off the main entrance to the Wye.

St. Michaels

Historic St. Michaels, a major yachting center, is only five miles downriver, but the harbor is small and better holding ground is outside (serviced by water taxis). A free dinghy dock is also available. Members of the Chesapeake Bay Maritime Museum often grab available slips, but marinas cater to transients and one can usually find a place somewhere. Bed-and-breakfasts are all over the place.

Restaurants abound, some of them quite good but expensive, such as 208 Talbot and The Inn at Perry Cabin. My favorite, a locals hangout, is the casual Carpenter Street Saloon on Main Street. If I can hitchhike a ride to and from nearby McDaniels, I’ll buy a pound of jumbo lump Bay crabmeat at Chesapeake Landing, which might be the best medium-priced restaurant in the area.

Oxford bound

As long as the wind isn’t dead out of the south or southeast, my all-time favorite destination is Oxford on the Tred Avon River, some 32 miles from Annapolis. Crossing the Bay I head south for 22 miles to Knapps Narrows, a canal through Tilghman Island and a shortcut to the Choptank River. A center for workboats, it is only a few miles long and lined with restaurants, marinas, boatyards (Carl Grieble’s Severn Marine Services being one of the best) and local boatbuilding legend Maynard Lowrey.

Depending upon my mood, after opening the bascule bridge I can hang a right and head directly to Big Buddy Harrison’s Chesapeake House in Dogwood Harbor for music and a pool. Tying up at one of the docks filled with charter fishing boats, I might sit down for an excellent fried seafood dinner or take it out and motor a short distance to nearby Dun Cove, off Harris Creek, to anchor in peace for the evening and avoid the human commotion at Buddy’s.

Broad Creek and Grace Creek

Broad Creek, halfway between Dun Cove and Oxford, is a maze of smaller creeks (Balls, Leadenham, Grace, and San Domingo) with a wide entrance flanked by two extraordinarily long, marked sandbars along the north side of the Choptank.

Many bypass this interesting cruising ground in their rush to reach Oxford, about 10 miles from Knapps, and this is unfortunate because one can spend a couple days here gunkholing. Once inside, there are many coves and branches and even islands to explore, along with quaint watermen’s villages, such as Neavitt and Bozman. The “back door” of St. Michaels is reachable by dinghy from the headwaters of San Domingo Creek, and a mile or so from town.

Grace Creek is the Bozman home of P.T. Hambleton’s Marina and commercial crab-packing and trucking operation, a colorful place to buy fresh softshells and hardshells. Operated by several generations of Hambleton’s family, a visit to the “office” (where Hambleton is always on the phone) and observing the softshell shedding operation is an entertaining experience in itself. While there, try and figure out what everyone is talking about in the native dialect.

Oxford on the Tred Avon

After finishing off a mess of softshells fried in butter, the next point upon leaving Broad Creek is Benoni — another long, marked sandbar at the mouth of the Tred Avon. Oxford, the prettiest village on the Bay, has an active sailing community and is a lively weekend destination for many regattas, with sailors arriving at the Tred Avon Yacht Club to eat, party, accept awards and dance away the night.

Historic Oxford dates to 1683 and is not touristy, but it is a boating center with many excellent marinas and boatyards, most of them on Town Creek. Vehicular traffic on a non-regatta weekend is nothing like that of St. Michaels, and there are no traffic lights or parking meters to feed. The nation’s oldest privately operated ferry shuttles pedestrians and cars back and forth across the river to Bellevue.

Charming restaurants are sprinkled about in nooks and crannies, along with small B&Bs and the historic Robert Morris Inn with its elegant, somewhat formal dining room. One of the best restaurants is Latitude 38, a mile or so outside of town that operates pick-up and deliveries for those arriving by boat. Latitude 38 has also taken over the 150-seat riverfront Pier Street Restaurant, severely damaged by Tropical Storm Isabel, and hopes to be open by mid-July with a 67-slip marina offering dockage for diners.

The almost mile-long “Strand” bordering the river has a sandy public beach with a free dinghy landing, plenty of ducks and shade trees. The exposed anchorage is geographically ideal, except it has poor holding ground and offers little protection from weather fronts that might roll through. Anchoring is also readily at hand in Town Creek, but many other creeks are just minutes away and more peaceful, especially on weekends.

Oxford is a wonderful place for strolling and bicycling, but, sadly, Bill Bringman’s mom-and-son confectionery and newsstand — once operated by the late Bill B., who towered over his mother — has closed and is now the Oxford Museum. Nearby, however, the Oxford Market still sells hand-dipped ice cream, home-baked pies and fresh vegetables, sandwiches and spirits.

Across the street is the waterfront town park with picnic tables, benches and a sandy beach. This is an ideal setting to watch an ongoing parade of cruising yachts coming and going, and the last leg of races from Annapolis.

A cruise to Oxford would not be complete for me without paying respects at Cutts & Case Shipyard — a boatbuilding center (and museum) of lovely wooden boats, mostly sail — next to the former Crockett Brothers Boatyard and Marina, now a Hinckley facility.

I have been coming to Ed Cutts’ old-fashioned family boatyard for more than 30 years and relish it for changes that have never even been considered. They still haul boats on a marine railway and with an ancient tractor-crane, but a few years ago they bowed to modernity and installed a shower facility. But don’t ever expect them to open a ship’s store and sell T-shirts, hot dogs and bags of ice.


The Western Shore of the Bay also provides some favorite weekend and overnight getaways from Annapolis — Galesville on the West River, Ridout Creek off Whitehall Bay, and Eagle Cove and Gibson Island off the Magothy River.

Again, wind direction and mood are my determining factors, but these distances are a lot shorter (less than 15 miles) and more time might be spent just in pure sailing on the main Bay before ducking into an anchorage or to tie up when I get my fill of sailing.

Galesville is a little village a dozen miles south of Annapolis with marinas, at least one good restaurant (Pirates Cove) you can count on being open, and an authentic country store serving homemade pies and sandwiches to be consumed al fresco in a picnic area shaded by sun umbrellas, usually in the company of neighborhood dogs.

A brisk, 1-1/2-mile walk will take you to one of the Bay’s best, oldest and largest working family boatyards with a marine railway, Hartge’s Yacht Yard. A Hartge yachting museum is also worth visiting, especially if curator and family historian Laurence Hartge is on hand. Showers are open to cruisers and there is an excellent ship’s store and ice house that still sells block ice on the honor system.

The county pier offers free dockage, although boaters are not supposed to tie up overnight. If you do, however, expect to be awakened before dawn by boatless amateur crabbers (those chicken neckers) who drape the rails in crabbing lines and crowd the deck with baskets, crab nets and coolers. There is room to anchor in and around a mooring field where boaters have dropped permanent moorings.

Quiet anchorages

But a peaceful getaway anchorage is just a few miles away up the Rhode River and behind Big Island, which is more or less surrounded by an undeveloped mass of land preserved and protected by the Smithsonian Institution’s Environmental Research Center. The shoreline is posted (but not patrolled) as a “No Trespassing” zone and the only people you’ll come across will be fellow boaters in raft-ups.

Closer to Annapolis is Whitehall Bay, just a couple miles from the busy harbor, which offers a choice of dining at Cantler’s Riverside Inn, a somewhat overrated but very popular crabhouse with an open deck overlooking Mill Creek. (My favorite crabhouse in the area is at the Kentmorr Marina on Kent Island just across the Bay on the Eastern Shore.)

The anchorage in Whitehall is exposed and unprotected from a southerly, but boaters use it in the heat of summer and there is an empty beach to explore on the preserved, undeveloped peninsula of Hacketts Point. Good shelter, however, is just around a dog leg at the mouth of Whitehall Creek and into Ridout Creek, a lovely, quiet and narrow deepwater anchorage with a few private docks and handsome homes.

Gibson Island

If it’s blowing really hard from the south, I’ll motorsail out of Annapolis and crack open my roller-furler jib at the “spider,” and duck inside this high, discontinued navigational structure off Greenbury Point and head north for the Bay Bridge(s) and Gibson Island, a 15-mile daysail.

With sandy Point State Park to port, I’ll zip inside the Sandy Point Lighthouse and blast through the busy and narrow mouth of the Magothy River with the island to starboard. Ahead and off to port is popular Dobbins Island and Sillery Bay, which usually has a mall of anchored boats, water skiers, and PWCs zooming about. That is not for me.

Rounding the northern end of Gibson Island and entering the Magothy Narrows, I have a choice of anchoring in Eagle Cove to starboard for a quiet night with none of the frenzied activity and wakes dished out at Dobbins.

Or, if I’m in the mood for an excellent dinner and to socialize, I’ll call Denver Sanner, Gibson Island’s dockmaster, for a guest mooring or overnight dockage at one of the piers where I can expect to be awakened by Denver firing off his 8 a.m. shotgun blast.

This is a private island with a gatehouse and a protected harbor filled with some 50 moored sailboats owned by members of the Gibson Island Yacht Squadron. It’s a restricted paradise for those resident rich folks and a pleasure to visit.

A family friend, Gibson Island yachtsman J.P. Watson, whose parents live there, clears me for dinner at the club, which is open only to members and their guests. It’s a lovely 1-1/2-mile, cigar-smoking stroll to and from the clubhouse.

By 8 a.m. the next day, after stocking up on ice, I’m on my way back home to Annapolis.