Constructed in 1753 on Howard's First Choice, a tract patented in 1668 and expanded by Charles Worthington in 1704, the Rising Sun Inn is a rare intact 18th-century tavern and dwelling on historic Generals Highway that served travelers and horses and remained an active part of the community for nearly 270 years. Worthington sold the property in 1753 to Edward Baldwin, who built the earliest surviving section, and after the land was divided in 1759, Lt. Henry Baldwin, a Revolutionary War veteran and quartermaster in the 2nd & 3rd Maryland Line from 1777-1783, supplied the Army with tobacco from his plantation. After the war, Henry Baldwin and Sarah Hall Rawlings enlarged the building and began operating Baldwin's Tavern in 1785; after Sarah's death and Henry's death in 1793, Maria Baldwin continued the business and, after marrying Augustine Gambrill, the tavern became Gambrill's Tavern until 1815. It served as the heart of the local community, functioning as a stagecoach stop, post office, tax collector's stop, and meeting place for legal and business matters. Richard Caton and Mary Carroll purchased the inn in 1819, and after several later transfers it stood vacant in 1913 before being bequeathed in 1916 to the Ann Arundel Chapter of the National Society Daughters of the American Revolution, organized in 1911 by Alice Leakin Welsh of Waterbury. Under that chapter's ownership for more than a century, the inn has been carefully restored, used as a chapter house, and at various times served as a Red Cross work center, a recreation center for Ft. Meade soldiers in both World Wars, and a tea house; today it is a historic museum and chapter house. Architecturally, it is a combined wood-frame and brick example of 18th-century rural Chesapeake building, with a c. 1753 one and a half story central hall dwelling section with gable roof and a massive brick gable-end internal chimney in header bond, and a 1784 gambrel-roofed addition by Henry Baldwin that opened the full first floor to tavern use; it was listed in the National Register of Historic Places in 1985. In the 1700s, Generals Highway was a major stagecoach corridor between Baltimore and Annapolis, later associated with George Washington and the French Major General Comte de Rochambeau during the Revolutionary War, and although the road was straightened when paved in the early 20th century, the inn's orientation still recalls the colonial road's original course.