On this unforgettable evening stroll, maritime history meets tragedy, war, and mystery as you hear the tales of barmaids, spinsters, and ladies of the evening—women whose lives were tied to the darker side of hospitality and whose stories still echo through the town’s narrow streets. Along the misty banks of the Miles River, you’ll discover how love, loss, and longing may have left more behind than memories.

By daylight, St. Michaels charms visitors with its waterfront beauty, elegant shops, and celebrated restaurants. But after dark, another side of town emerges. The spirits of sea captains, war heroes, sailors—and the women who once loved them—still seem to stir beneath the surface.

Join us for a captivating guided walk through town as we share these chilling stories at the very locations where they unfolded.