"We'll be in the money," predicts Captain Jack Russell, skipper of the skipjack Dee of St. Marys.

Russell, 40, is not making an economic forecast on the oyster-dredging season, which opens in Maryland this Tuesday. He's predicting a win in the last hurrah for sailing oyster boats before this grueling season begins -- the annual skipjack races that will be run this weekend as part of Chesapeake Appreciation Days at Sandy Point State Park in the shadow of the Bay Bridge. Along with the skipjack races, the two-day festival will feature powerboat races, an air show, skydivers, live music, arts and crafts exhibits, jousting, oyster-shucking and -cooking contests, and lots of oysters -- and other seafood -- to eat.

Russell's Dee, built at Piney Point in St. Mary's County in 1979, is one of the newest of the fleet of long, beamy shallow-draft sailing workboats that ply the Chesapeake in pursuit of the succulent bivalves. At the turn of the century, there were about 1,500 of them. But at last count there were only 34 still working the Bay, and at least half the fleet will be racing off Sandy Point this weekend.

Once skipjacks raced to port, the winners gaining the highest prices for their oysters. Today, the price -- currently between $12 and $15 a bushel -- is set by some sort of mystical communication among wholesalers, and the skipjacks simply race for a trophy. Their most important race, however, is against time.

A Maryland conservation law that restricts oyster dredging to sailing vessels also conserves the skipjacks, romantic anachronisms with soaring bowsprits, gold-etched trailboards and towering masts. Other, less romantic-looking craft may tong for oysters, but the more efficient dredging method is reserved for the skipjacks. The vessels have no internal motors, but they lower "push boats" off their sterns to get them from port to the oyster beds. The push boats, powered by huge automobile engines, may be used instead of sails in the oystering operation on Mondays and Tuesdays -- an additional concession to preserve the working skipjack. But from Wednesday through Saturday, the huge sails must find enough wind to drag the heavy dredges along the bay bottom. Maryland's skipjacks make up the sole surviving commercial fleet under sail in the United States, and Bay buffs fear that these, too, will vanish into the past. But three new skipjacks -- the Dee of St. Marys, the Minnie B. and the Anna McGarvey -- have been built in the past four years, pointing to a skipjack revival of sorts.

One of the goals of the annual Chesapeake Appreciation Days is to rekindle appreciation of the iron men in their wooden skipjacks, but spectators watching the great sails turn pink in the sunset this weekend should throw out any romantic notions with their oyster shells: A waterman's life is a hard one.

"The work is grueling -- you have to be strong to work the dredges and you're bent over all day," says anthropologist Paula Johnson, who has sailed with skipjack crews to gather material for a coming exhibit on commercial fishing people at the Calvert Marine Museum.

"We get up two hours before daylight to start dredging at sunup," says Russell, who will work the waters with a crew of five this season. "I had an oyster-shucking house, and I always saw those sailboats. Four years ago I decided to build one -- it was my doctorate in the water business. I've worked it for three seasons now, four-and-a-half months a year, and it's a good life. There are no bosses, no time clocks. Sure, it gets cold. It's a hardy life. When it gets cold, you just pull on more long drawers." APPRECIATING THE CHESAPEAKE -- Chesapeake Appreciation Days will be held Saturday and Sunday at Sandy Point State Park, just this side of the Bay Bridge on U.S. 50. Gates open at 9 and close at 5 both days. Skipjack races start at 10:40; before and after the races, visitors may board the skipjacks, which will be docked at the park. Admission is $3 for adults and $1.50 for children 6 to 16. Admission includes parking and exhibits. Food is extra.