- 172 Main Street (1890)--Roxbury Inn, built by Colonel Richard Cutts Shannon, Civil War officer who served at Gettysburg and minister to two South American countries. The most notable surviving archilectural feature is the massive tile roof.
- +25 College Street-Historical marker on parking. This house and the one next door east formed the "Brown Coltage" of Mary Jane Holmes, whose 50+ novels brought popular literature to late 19th century American women. Her husband, Daniel, was a prominent local lawyer, civic leader, and member of the Brockport Normal School council for 50 years.
- +*39 College Street (ca. 1870)-Victorian ltalianate style, with off-center cupola and centered oculus window, decorative details on cupola and corbels, large carriage house, deeply curved arch over front door.
- 40 College Street (ca. 1850s)-Greek Revival style, built by Hiel Brockway, co-founder of Brockport, the Blue Pitcher Tea Room, 1917-36.
- *46 College Street (1907)-Four-square, arts-and-crafts style popularized by Elbert Hubbard, large wrap-around porch, leaded-glass windows, flank front door and in center of 2nd floor facade, property owned at various times by leading Brockport families.
- 56 College Street-Red brick ltalianate, with corner tower and distinctive stone quoins and lintels, built by L. T. Underhill, leading local lumber dealer and builder. Mansard roof added later.
Continue west to Utica Street
- +*75 College Street (ca. 1860)-Second empire style with intricate woodwork and mansard roof, built by Edward Harrison, merchant and civic leader, sold to Brockport Normal School by his daughter (1898) and used as the principal's and, later, president's residence, transferred to Brockport Alumni Assn. (mid-1980s), extensively restored by it.
- +Hartwell Hall (1941)-Neo-Georgian academic structure, oldest building on SUNY Brockport campus. Historical marker at flagpole. Site of institution of higher education since 1834. Recently renovated as $15 million project that respected its historic architecture.
Turn right and walk north on Utica Street to Monroe Avenue
- *61 Monroe Avenue cor. Utica (1861)-Methodist parsonage for ca. 125 years.
Continue north on Utica Street to Holley Street
- +*34 Utica Street (late 1820s)(one block north of Holley Street, northwest corner)-Wood frame residence, built by Hiel Brockway and owned by his lamily until 1902. Brockway was co-founder of Brockport, the world's largest builder of canal packet boats, and the owner of a brickyard and packetline between Rochester and Buffalo.
- Holley Street-The Nativity of the Blessed Virgin Mary School, founded 1876. North wing was built in 1854 as a church. South wing was built in 1915.
Turn right and walk east on Holley Street
- 45 Holley Street (ca. 1860)-Modified carpenter Gothic style with restrained use of decorative woodwork of Egyptian influence.
- 17 Holley Street (1832)-Built by Brockway and later owned by William Seymour, porch added in 1872.
- +124 Main Street (1863)-First Baptist Church, unusual assymetrical towers.
For Segment E Turn left and walk one block north on Main Street to Erie Street to Stop 62.