- The Erie Canal-Built between 1817 and 1825 and enlarged later several limes, the canal was the first means of mass transportation into the American Midwest and opened that great region to settlement. Brockport was its western terminus for some two years.
- Main Street lift Bridge (1915), +lift tower (1913) - This span and the one a block east are two of only sixteen lift bridges still in operation on the canal. A third span one block to the west is a fixed, high bridge. They were built as part of the last reconstruction of the canal.
- *Brockport's Historic Commercial District - The 45 commercial buildings on both sides of Main Street from the canal to the State St./Erie St. intersection and on Market Street were designated an historic district by Brockport's Historic Preservation Board in 1999 and are being nominated by it for listing on the state and national registries of historic places. They form the largest, intact array of Victorian commercial buildings in the area.
Walk south on Main Street
- *1 Main Street (1867)-one of the seven toll stations on the Erie Canal was located on the lower floor. Unusual lintels, bracketed cornices, and cast-iron ornamentation and pilasters. Rear and south walls are Medina sandstone. Top floor may have been an auditorium.
- *9-11 Main Street (1886)-Cast-iron pillasters, lintels (including dragons), cornices, and pediment.
- *13-15 Main Street (ca.1834)-Cast-iron columns and stone cornice.
- *21-25 Main Street (ca. 1834)-Bay windows and corbelled, brick cornice. The storefront retains much of its original design.
Cross Water Street and continue south on Main Street
- *39-41 Main Street (1871)-Brockport's most distinctive commercial structure with its contrasting brick and stone wall finishes, cast-iron columns, arched stone lintels, dentiled cornice, stone pilasters, original finials, pointed-arch pediments, third-floor auditorium, and restored "Ivory Soap" sign.
Turn left (east) on Market Street
- *5-9 Market Street (1883)-Arched stone lintels, pressed-metal cornice, and curved pediment.
- *11-13 Market Street (1877)-Metal detailing on the staircase doorway, curved decorative stone lintels, and elaborate pressed-metal cornice and pediment.
- *19-25 Market Street (ca. 1881)-Eight original, decorative, cast-iron columns; elaborately-detailed brickwork; cast-iron first-floor cornice; brick and wood second-floor cornice; and "little brother" west wing.
- *27 Market Street (ca. 1881)-Decorative wood lintels and sills with shouldered side moldings and bracketed wood cornice with pointed-arch pediment.
- +38 Market Street (1969)-The main village fire station houses several pieces of antique firefighting equipment.
- +*14 Market Street (ca. 1881)-Extraordinary decorative brick work and arched wood panels under the lintels.
Return to Main Street, turn left, and cross Market Street (headed south)
- *43 Main Street (ca. 1861)-little changed from its 19th century appearance. leaded-glass transom window, beautiful stone and brick lintels, paneled knee walls, cast-iron columns with relief detailing, and elaborate, bracketed cornice on two elevations. Interior has pressed-metal ceiling.
- *53-55, *57-59 (both ca. 1861), and *61-65 Main Street (ca. 1840s)-Similar buildings with harmonious variations and a consistent rhythm in the fenestration and detailing. 53-55 has decorative cast-iron pillars and cornice and transom windows. Lintels of 57-59 form continuous stone band. Large wood 3rd floor cornice has elaborately-decorative brackets. 61-65 has large, leaded-glass transoms, remarkable 3rd floor lintels, cast-stone pilasters and knee walls.
- *67-71 Main Street (1916)-The district's only neo-classical commercial building, with cast-stone pediment, moldings, bases, and Ionic capitals and large, leaded-glass transoms.
- *79 and *83-87 (its big brother) Main Street (ca. 1880s)-1st floor pressed-metal cornices with finials topped by balls. Marble horizontal stringcourses on the 2nd and 3rd floors. Ornamentation features High Victorian motifs.
- *89-93 Main Street (1907)-Since 1916, this building has housed the Strand movie theater, the oldest in the Rochester area. The Streamline Moderne facade, with black Carrara glass, was added in 1946 (Michael J. DeAngelis, architect). A 1930s movie projector is displayed in the lobby.
For Segment B turn left (east) on State Street for Stop 20.
For Segment C continue south on Main Street to Stop 42.
For Segment D continue south on Main Street to South Street and cross Main Street to Stop 48.
For Segment E cross Main Street to Stop 62.