The following year the war took a grimmer turn when the Americain brig Enterprise and HMS Boxer fought a brief but bloody battle east of Portland between Pemaquid and Monhegan. There is a folk tale that Captain Moody watched the engagement through his telescope and relayed a broadside-by-broadside account to the crowd on Munjoy Hill, but th Observatory would have had to have been quite a bit taller for Moody to see anything. The Enterprise was victorious, but at a cost. Captain Blyth of Boxer was killed almost immediately in the action. Captain Burroughs, of Enterprise, was mortally wounded but lived long enough to learn that he had won. Next day the two vessels came into Portland and moored at the end of Union Wharf. Though Enterprise seems to have come out of the battle with relatively minor damage, an eyewitness reported that, among other things, Boxer had taken "eighteen or twenty 18-pound shot in her hull, most of them at the water’s edge...and such a quantity of small grape that I did not undertake to count them." When the two captains were buried in Eastern Cemetery, in adjacent graves, on 8 September, members of the Portland Marine Society marched in the funeral procession, just behind the "Civil Officers of the State."
Marine Society member Captain Thomas Merrill, Jr. bought Boxer's remains for $5,600, repaired her and put her under Captain Williar McLellan (not a member). She seems to have lasted until about 1845. Enterprise became a guard ship off Charleston, performed anti-piracy duty off the West Indies after the war, and was wrecked in 1823.
The first quarter of the century seems to have been a good one for the Marine Society. Between 1800 and 1825, it admitted one hundred forty-six members, followed by seventy—five more from 1826 to 1850. In 1800 the Portland Gazette commented approvingly that "from the liberal and benevolent principle on which this institution is founded, from the accession of members, which in the course of a few years, it has embraced, from the increasing state of its funds, and the enterprise of its members, the public may entertain the most flattering hopes of its future importance and utility." The first Committee on Relief, elected in 1817, was comprised of Captains Joel Hall, Lemuel Moody, William Woodbury, Thomas Robinson and Mr. John Watson. As far as can be determined, the first Committee of Observation was elected at the annual meeting of 21 December 1819, with Captain Enoch Preble as chairman and Captains Lemuel Moody, Thomas Robinson and Samuel R. McLellan as members.
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