- *237 South Main Street (1904)-Capen Hose Co. oldest fire station in the area in continuous use. Firefighting museum has 1847 hand-pumper, 1876 steamer, and 1936 Seagrave pumper.
- *291 South Main Street (1913)-Restrained Queen Anne style, leaded-glass panels flank front door, distinctive latticework on railings of wrap-around front porch
- *299 South Main Street (1831)-Pioneer settler Edward Parks farmed here from 1808 and built this large brick home, which remained in his family until l909. Later owners included artist Bertha Coleman and Monroe County School Superintendent Fred W. Hill.
- *307 South Main Street (1888)-Distinctive cupola on facade.
Continue south to Hillcrest Terrace, cross Main Street, and turn right (north)
- *320 South Main Street (1890)-Clapboard Queen Anne housing Victorian Bed-and-Breakfast. Recent addition consistent with original style.
Continue north, passing under railroad bridge
- 186 Main Street (1904)-Webster Funeral Home, built by Edgar Maynard and John Wadsworth with architect J. Mills. Corner pilasters with full height portico and four columns with Corinthian capitals, palladian-style front door.
For Segment D cross College Street, and turn left (west) at Stop 48.
For Segment E cross College Street and walk north on Main Street to Stop 62.