In 1884 fire consumed the wooden commercial buildings along the east side of Main Street from Merchants Row to Pleasant Street. Shortly afterward, Burlington architect A. B. Fisher designed an extended three-story brick structure to replace them. (Similar post-fire union blocks were built in many villages.) Containing individually owned commercial premises and a railroad hotel, the Union Block is unified in design. Pressed-metal cornices run above the store-fronts and on a corbeled-arcade eave parapet at the top of the block, and continue around the canted-corner entrance of the Red Lion Inn along the length of Merchants Row. Catering to railroad travelers, the inn boasted an ample lounge, dining room, and thirty-five “modern” rooms. When the block was completed in 1885, Randolph was a railroad and industrial commercial center more comparable to White River Junction and Montpelier than to rivals like Bethel and South Royalton.
Fire struck again in 1992, destroying the block's center buildings on Main Street. Local preservationists rallied and assembled public and private financing to fill the gap with the Winslow Block, named for the owners of the Ben Franklin store across the street. This 1995 Postmodern building has metal storefronts and a prominent block modillion eave cornice designed to be compatible with the remaining sections of the Union Block. The two-story building just south of the Union Block is also a replacement, here for the mansard-roofed DuBois and Gay Block destroyed by a fire in 1991 that miraculously spared the adjacent DuBois Bank Building (c. 1865), a one-story brick structure with a distinctive Baroque parapet.