Historic Odessa Known as Cantwell Bridge until 1855, Odessa developed as a bustling grain port and played a vital role in Delaware’s early commercial growth before suffering a period of economic decline after the construction of the railroad. Today, this tranquil town with pristine colonial buildings, tree-lined streets, brick sidewalks and a population slightly exceeding 300 seems untouched by time. Five of its most unique properties are known collectively as the Historic Houses of Odessa and are managed by the Historic Odessa Foundation. Visitors can take guided tours of these properties which showcase period rooms and furnishings crafted by prominent 18th- and 19th-century cabinet makers, silversmiths and artists. Odessa is one of only 13 National Historic Landmark sites in Delaware and the Corbit-Sharp house is a designated Network to Freedom site on the Harriet Tubman Underground Railroad Byway. Middletown Middletown is Delaware’s fastest-growing municipality and offers an appealing mix of stately Victorian homes and new construction. Middletown’s Main Street has an assortment of retail shops, restaurants and attractions including the historic 375-seat Everett Theatre. Family-friendly events like Old Thyme Peach Festival, Mud Race and Christmas Parade are part of the fabric of life in Middletown and make it a prime choice for those seeking a vibrant community atmosphere.