It was about a month after the incident above mentioned, that Timothy Webster completed his preparations for making his first trip into Virginia and through the rebel lines. A large number of Baltimoreans had intrusted him with letters to their friends and relatives in the South, and he had assured them that their messages would be delivered safely and answers brought back in due time.
He left Baltimore on the 14th of October, and proceeded southward along the "Eastern Shore" of Virginia, seeking a convenient place to cross over to the mainland or "Western Shore." He arrived at Eastville, the county seat of Northampton county, on Tuesday, October 22d, where he found that he could effect a crossing with the assistance of a man named Marshall, who made a business of smuggling passengers and mails through the lines. He was compelled, however, to remain at Eastville several days, waiting for Marshall and his boat to come over from the other side, his trips being delayed on account of the bright moonlight nights, as the boatman did not dare to run the gantlet of the Federal guns, unless covered by darkness.
Some two or three months before, this man, Marshall, had owned a sloop, which he had used successfully in running the Federal blockade. One night he was caught in a calm near the western shore, and was run-down by a gunboat. His sloop was captured, and he narrowly escaped capture by deserting his vessel and reaching the shore in a smaller boat. Since that time Marshall had been pursuing his vocation with a sort of canoe, or "dugout," thirty-one feet in length and five feet in width, carrying three sails—main, fore and jib. His route was from Gloucester Point, York river, to Eastville, and his business was to transfer from one side of the bay to the other the Confederate mail and passengers, and sometimes a small cargo of merchandise. Marshall being an expert pilot and a thorough seaman, was frequently employed by the masters of sloops and schooners to pilot them past certain points, they giving him the privilege of putting his passengers and mail-bags aboard the vessel without charge. It was his invariable custom to place a stone or other heavy substance in his mail-bag before starting, for the purpose of sinking it in case of being pressed by the gunboats.
It was on a dark evening that Webster left Cherrystone Lighthouse in Marshall's canoe, to make the voyage across the Chesapeake. There were thirteen passengers, all told. Eight of these were Marylanders, mostly from Baltimore, every one of whom announced his intention of enlisting in the Confederate army or navy upon his arrival at Richmond.
On starting, Marshall rowed off a short distance from the light-house, and rested on his oars for some time, taking observations to ascertain if the bay was clear of hostile craft. The night was scarcely dark enough for safety; the clouds were thin and scattered, and the stars were peeping through the dark, ragged curtain overhead. The wind was blowing strongly from the east, and the water was exceedingly rough.
Resolving, however, to make the effort, Marshall hoisted his sails, and as they rapidly filled, the little vessel sprung forward like a thing of life. It fairly skimmed over the waves, its sharp prow cutting the water and dashing up clouds of spray that caused the men to turn up their coat-collars and pull their hats down closer upon their heads. All conversation was forbidden, lest their voices should betray them to the enemy. With sealed lips and motionless forms, they might have been so many dark phantoms speeding before the wind on some supernatural mission.
Webster, by his own wish, had been put upon the look-out by the captain of the boat, and he keenly watched for signs of danger. When they had traveled nearly half the distance across the bay, he spied a point of light to leeward, and at once called Marshall's attention to it.
"It is a gunboat with a light on her bows," said the latter. "Let her come. She can't catch us, for with oar present headway we are not to be overhauled by any boat on this water."
The canoe was headed due west for about fourteen miles, then south-west by west for ten or twelve miles, then due west again to Gloucester Point. The entire run was made in three and a half hours, the sailing distance being about thirty miles.
On nearing Gloucester Point, they were hailed by a sentinel, with the usual challenge: