Crown City Touring- Main Street

Explore the history of the buildings on Cortland's Main Street.

Crown City Touring- Main Street

Cortland, New York 13045, United States

Created By: Cortland County Historical Society

Tour Information

Welcome to the walking tour of the Main Street downtown area in Cortland, NY! Cortland's Main Street has served the community as a shopping and entertainment district for over 200 years, and as we stroll along this charming thoroughfare, you'll discover the rich history and fascinating stories behind the historic buildings and businesses that have shaped the heart of this vibrant community.

This tour is still in development, so new spots and information will continue to be added!

Put on your comfortable shoes, be ready to dodge some construction, and join us on this captivating journey through time and heritage!

Find us on social media platforms to see upcoming scheduled tours led by City of Cortland historian, Kate O'Connell.

Tour Map

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What You'll See on the Tour

The first structure at 1 Main Street for which we have decent documentation is the Bernard Block, which according to the 1863 map included a boot and shoe shop, a milliner’s shop, and a dry goods and grocery store. D. Morris Kurtz briefly... Read more
Joshua Ballard is quoted in H.P. Smith’s “History of Cortland County” as saying: “The corner lot where stands the noble brick edifice of Major Aaron Sager and the Dexter House, was once occupied by a tavern building of ordinary size... Read more
The first known building on the spot that is now 9 Main Street was a wooden structure that shows up in the same photo depicting the corner of Main and Clinton that has been featured in past posts. The earliest I can trace the businesses bac... Read more
This location has the distinction of having had one of the last remaining family residences in Cortland’s business district! Believed to have been built in the 1830s, what is commonly known as the Keator House was torn down in 1937. But l... Read more
As we continue our historical tour down Cortland’s Main Street, we come next to the Garrison block, a stately structure encompassing numbers 17-21. The earliest description I can find for this location speaks of a long, low white building... Read more
This spot began as a residence with a neighboring store. I unfortunately had trouble determining when exactly the original house and store were built and by whom, but the land has connection to Tercius Eels and later Oren Stimson who were t... Read more
As we approach Central Avenue, we are taking a look at 31-33 Main Street which has over the years been referred to as the Union Hall block, the Collins block, and the Burgess block. But its beginnings are believed to stretch back to about ... Read more
Before the formation of Central Avenue, formerly called Railroad Street, a building stood on Main Street at what would become the street entrance. The first structure we can date there is from 1841 which is the earliest a business there ap... Read more
In 1843, Isaac M. Seaman began a grocery and meat business, described as the only one of its kind in the village at the time. He afterward partnered with Leavitt Cudworth until 1847. The mantle was taken up by B.K. Aldrich, followed by G.N.... Read more
41 Main Street is a small structure, but if we got our history right its bones are made up of one of the oldest buildings that remain on Main Street! In 1860, brothers Isaac and Martin Edgcomb purchased the lot south of Cloyes and Garrison... Read more
Messenger/Taylor Hall block: The Taylor Hall block is chock-full of history and stories, that it is simply impossible to cover it all here! To dive into all the events, performances, dances, masquerades, concerts, and speakers that graced t... Read more
This is another location where the early history is something of a mystery, and we can't even sure of the accuracy of some "facts." Smith’s “History of Cortland County” provides a date of about 1863 for an early structure, at which p... Read more
Next section is a triple-hitter with the First National Bank building, Fireman’s Hall, and the County Clerk’s Office building. The portion of Main Street that now contains 36 and 38 was once part of the Josiah Hart estate the extended t... Read more
This location started as the estate of Joshua Bassett (1757-1836). Joshua and his son were the first jewelers and silversmiths in Cortland, and their “shop was upon the same lot as the dwelling house…it was one of the handsomest as well... Read more
The history of numbers 22-28 Main Street in Cortland, like several other addresses previously covered, starts with a house. Sylvester Blair (-1836) built his home on the property “consisting of a large and advantageously situated village ... Read more
What is now an unassuming section of our business district once was witness to scandal, tragedy, and the beginnings of a success story. The history of 16-18 Main mainly covers two structures; the first started as a brick building put up by ... Read more
The history of Cortland’s #14 Main Street overlaps somewhat with that of #12. The two addresses were once part of one property with a residence at #12, and #14 acting as an office. In the 1850s, the office was used by attorneys Robert O. ... Read more
The earliest building that appears on maps was an L-shaped brick structure that at the time was the residence of Robert O. Reynolds (1811-1855). Reynolds was partnered with Hiram Crandall as attorneys and counselors at law, and their office... Read more
The first structure on the southwest corner of Main Street and present-day Groton Avenue (at one time named Cortland Street) was called the Lyman Block, a two-story brick structure which is said to have been built around 1816-1817 by Asahel... Read more


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