You don’t need to download “The Walking Tour of The Chestnut Street Historic District and Neighborhood” that the Friends of Historic Kingston (fohk.org) have put together to take a perfectly pleasant walk around one of Kingston’s most impressive neighborhoods. But if you do, you’ll get to open a time capsule from a pivotal, captivating period of the city’s history and look inside.
Chestnut Street is a designated national historic district that’s roughly bounded by West Chestnut Street, Broadway, East Chestnut Street, Livingston and Stuyvesant streets. It’s a section of the city that spotlights Kingston history during the 19th and early 20th centuries, when technological and scientific advancements fueled the Second Industrial Revolution and created a class of wealthy entrepreneurs. The moguls came home to the mansions they built on West Chestnut Street, many of which still stand as residences today.
In 1851, James McEntee — an engineer who helped build the Delaware and Hudson Canal — bought 52 undeveloped acres up on the hill overlooking the Village of Rondout and divided it into building lots that would attract prominent, powerful families. Their influence and fortunes would extend far beyond the tree-lined streets of their privileged enclave to shape the lives and landscapes of America and beyond.
It was an era when generations of Huttons of the Hutton Brick Works lived on West Chestnut. William, the patriarch, and his wife Jane were in the Italian Villa- style house at No. 32. Their seven children and family members would live in four different houses on the street.
George Washburn, another brickmaker, lived at No. 28 with his wife Eleanor. In 1905, there were more than 30 brickyards along the Hudson, and the Hutton and Washburn yards were among the largest.
About 1895, Samuel D. Coykendall, principal owner of the Cornwell Steamboat Company, and his wife Mary moved into the towering three-story Gothic-Victorian-style, 5000-square-foot mansion at the top of West Chestnut. The architect was Calvert Vaux, the co-designer of Central Park and business partner of Frederick Law Olmsted in the firm of Olmsted, Vaux and Company. The only remaining evidence is the round stones in front of the houses now at Nos. 80 and 84 that mark entrances to what was once the grandeur of the Coykendall estate.
George Coykendall, Samuel’s brother and president of the Stony Clove Railroad, lived across the street at No. 77. His house is still there with an iron post by the curb that is thought to be the only surviving gas lamppost in Kingston.
Samuel Coykendall’s house is gone, but his Coach and Stable building isn’t. In 1894, he purchased the property at the corner of West Chestnut and Augusta streets to build a place to keep his horses and carriages. By 1950, that need was long gone, and the coach house was up for sale for a few thousand dollars.
A local fledgling community theater group formed a New York State non-profit corporation, bought the building, and changed their name to the Coach House Players (coachhouseplayers.org/). The Coach House Theater hasn’t missed a season in over 70 years, with four performances a year. It’s the longest operating community theater company in Ulster County.
The original pedigree of the historic building is unmistakable, but the horse stalls have been replaced by the prop shop. The hayloft upstairs is a massive closet with thousands of costumes collected over the years. The former coach room is the performance space, with a stage and 99 refurbished theater seats donated by UPAC.
Air conditioning, electric-system upgrades, expanded on-site parking – all the work is done by unpaid volunteers. “Drinking Habits,” a light-hearted comedy by Tom Smith, opens the 72nd season on April 1 and plays through April 10 on Friday, Saturday and Sunday nights.
Lowell Thing lived on Chestnut Street for more than 40 years in the ten-room Victorian at No. 55 and wrote The Street That Built a City: McEntee’s Chestnut Street, Kingston and the Rise of New York, the definitive book published in 2015. House by house, the author looked into the street and learned of all the residents of the district.
Along with the wealthy and powerful, the industrial growth of the era created a comfortable, thriving middle class of working people — the artists, actors, lawyers, physicians, cigarmakers, ship carpenters, teachers, shopkeepers, many immigrants who worked on the boats and docks and brickyards who had lived in the district. Lowell Thing writes about them all. The walking guide takes you to where they lived on Broadway and East Chestnut Street, Syuyvesant and Livingston streets.
McEntees, Coykendalls, Huttons and most of the other early residents of the West Chestnut Street neighborhood are buried in Montrepose Cemetery (75 Montrepose Cemetery), a block away from West Chestnut Street. The cemetery, formed in 1850 by Rondout’s leading citizens, has the history of the area written across the rolling, naturalized landscape that’s become a special kind of park for walkers and joggers today.
The tour starts at the fork of Broadway and Delaware Avenue, winds around through East Chestnut, Livingston, and Stuyvesant streets, and then goes straight up the hill to the end of West Chestnut. The free pdf is available on the City of Kingston website (Kingston-ny.gov). Search “Chestnut Street” to download.
Then get smart. Grab your guide and starting walking.
Join the family! 
