The year 2025 marks the 250th anniversary of the start of the American Revolution. In honor of that occasion, this walking tour calls attention to sites in the Village and to individuals who played a prominent role then and since. We should note there are equally important sites not included in this tour that lie outside the Village in the surrounding Town of Rhinebeck, sites associated with individuals who also played significant roles in the Revolution: Colonel Henry Beekman Livingston (at the Kip-Beekman-Heermance house on the road to Rhinecliff), Colonel Philip Schuyler (Schuyler House off Miller Road just east of the Village), Surgeon General Dr. Thomas Tillotson and General Morgan Lewis (both southwest of the Village and south of Rhinecliff).

Not incorporated as a Village separate from the surrounding Town until 1834, the history of the Village nevertheless pre-dates the Revolution. As far back as 1703 the predecessor of the current Route 9 was known as the Albany Post Road, linking mail service from New York City to Albany. Rote 308’s predecessor, Sepascot Indian Trail, connected Kipsbergen (today’s Rhinecliff) with Connecticut. By 1766 Arent Traphagen had built a tavern at this crossroads. In 1732, the earliest version of the Reformed Church stood to the south on land donated by Henry Beekman. Further south a stream named after local miller Casper Landsman carried sufficient water to power ten mills between its origin at Lake Sepasco and six miles downstream where it entered the Hudson at Vanderburgh Cove.

Route of this walking tour: Refer to the centerfold map.
Distance: about a mile and a half for the full tour
Time: about 2 hours

1. DELAMATER HOUSE

6425 MONTGOMERY ST.

Delamater House was designed by Alexander Jackson Davis in 1844 for Henry Delamater, founder in 1853 of the First National Bank of Rhinebeck. Later owned by General Ross Delafield, this style of house is called Carpenter Gothic and is among the best examples of Gothic Revival architecture. Images of the house have been widely reproduced. It currently serves as a guest house for the Beekman Arms complex.

INTRODUCTION

2. THE STARR INSTITUTE

6415 MONTGOMERY ST.

The Starr Institute, an 1862 Victorian Gothic style building, was given to Rhinebeck as a library and community hall by Mary Regina Miller, a descendant of Col. Philip Schuyler, in memory of her husband, Congressman William Starr Miller. The building was used to hold religious services when some local churches were built or restored. It was also a YMCA and a bowling alley, serves multiple uses today including over 50 years as host of Upstate Films.

3. FOSTER'S COACH HOUSE

6411 MONTGOMERY ST.

Foster's Coach House, which dates from about the 1850s, took its current name from Wallace Foster, a seasoned innkeeper who had managed the Eagle Hotel in Kingston, then the Beekman Arms for over a decade, before moving across West Market Street to set up another inn, which he would own and manage from 1933 until 1954. He was a serious horseman, and the present interior, complete with horse stalls, race horse prints, and a coach owned by Levi P. Morton maintain the atmosphere he created.

4. TEMPERANCE HALL

6406 MONTGOMERY ST.

Temperance Hall dates from about 1840 and is believed to be the oldest structure in the Village originally intended as an office. It was probably built for one of the Livingstons practicing law in Rhinebeck at that time and was used by John Armstrong, Jr. The 1867 Beers Atlas identifies its occupancy by Town Supervisor and NY State Assemblyman Ambrose Wager. As the Women’s Exchange in the 1920s, it gave local women an opportunity to add to family income through their culinary skills and needlecraft. For most of the twentieth century three murals above the door (now in storage) highlighted Indian and Revolution subjects. They were commissioned by Harry Hill and painted by Tivoli artist von Thum. The building is now a retail business.

5. BEEKMAN ARMS

6387 MILL ST.

In 1705, Judge Henry Beekman, a resident of Kingston, sold 281 acres to William Traphagen, most of it in the northwest corner of what today is the Village of Rhinebeck. William was a wheelwright & blacksmith, and the location on the east-west Sepasco Trail would have been ideal for someone who could shoe horses and repair broken carriage wheels and axles. By 1710, William’s stepson Arie Hendrickse had taken title to the property. Arie was a brewer and later accounts speculate his home (a little west of the Beekman Arms, on the north side of the trail) was the first inn here, offering lodging and refreshments to travelers. But William died in 1739 and Arie died in 1746, so it was probably Arie’s widow with her second husband, Jacob Kip, who built the inn on the site of the current Beekman Arms, about 1766. The low-ceilinged rooms in the central part of the building and thick stone walls show that the original structure has been contained within the present building. Facing on the Albany Post Road with riders regularly delivering the mail between NY & Albany and soon with a stagecoach traveling the distance, the inn was in an ideal location. Traffic from the river, traveling east toward New England also passed here. By the time of the Revolutionary War, the owner was Everardus Bogardus. During the war, his brother, Lieutenant Benjamin Bogardus, fought in the various battles around New York City. Where a memorial stone is located today, closest to the intersection, there was a town pump. This began as a natural spring that offered refreshment to all and watered the horses of the travelers. The inn was known as The Rhinebeck Hotel until 1918, when local entrepreneur Tracy Dows invested in complete renovation, added the ballroom to the south, and at which time it was re-named The Beekman Arms.

6. THE RHINEBECK POST OFFICE

6383 MILL ST.

The Rhinebeck Post Office was built in 1939 as a WPA (Works Progress Administration) project to make work during the depression. It replaced the earlier Rhinebeck Town Hall, which moved to East Market Street. President Franklin D. Roosevelt, who lived nearby in Hyde Park, suggested that the new Post Office be designed as a replica of the first stone house built in Rhinebeck. That house with its frame additions burned down in 1910. Note that there is a round window near the roof, on the side facing the Beekman Arms. It mimics a round puncture in the wall of the original house caused by a British cannonball fired at the house from a British naval vessel in the Hudson River. This occurred in 1777 during the Revolutionary War. Inside the front door on the right is a display showing pictures of the couple who built the house. The original carved lintel stone from that house is on display with their initials and the date, 1700. Above that display and around the interior of the building are murals painted by local artist Olin Dows illustrating the settlement and development of Rhinebeck.

7. THE ASHER HOUSE

6380 MILL ST.

The Asher House, now a restaurant, is among the oldest extant buildings in the Village, dating to about 1800. Early 20th century occupants included Wilson Applegate, President of the First National Bank of Rhinebeck (lettering of which is still barely visible above the street windows of today’s M&T, across the street), and Russell Applegate, whose insurance office occupied the first floor, and Frank Asher in the 1940s.

The Astor Home for Children occupies land once known as Bois Dore (Golden Woods) in the 19th century when owned by Robert Huntington. While living here in June 1888, Levi P. Morton learned of his nomination to run on the Republican ticket for Vice-President with Benjamin Harrison as President. They won the election. Since 1917, the site has served needy children. Morton’s daughter Alice had opened a home for convalescent children in Rhinecliff in 1905, which moved into a more modern building on this site when Robert Huntington’s daughter, Mrs. Vincent Astor, gave the estate in trust as a home for children.

8. THE ASTOR HOME

6339 MILL ST.

9. THE DUTCH REFORMED CHURCH

6368 MILL ST.

The Dutch Reformed Church, first church in the village, was a frame construction wooden church built in 1731. The present building dates from 1808. Brick sides face Mill and South Streets, the less expensive stone sides face the cemetery and rear of the church. Plaques on the pews and memorial tablets in the walls are of interest. Interior details are by master carpenter Steven McCarty.

10. REFORMED CHURCH GRAVEYARD

1 SOUTH ST.

East of the church, along South Street, the graveyard contains forty-three American Revolutionary War heroes. Some gravestones date back to 1733. Note also the historic bell (from the Rondout Lighthouse) and Revolutionary-War-era cannon and placed there as memorials.

South Street was originally a Native American path known as the Sepasco Indian Trail and the oldest street in Rhinebeck. The trail parallelled a stream to its south, the Landsman’s Kill, and led to Sepasco Lake east of Rhinebeck, once the site of a Native American village. By the Revolutionary War, it became the primary route eastward out of Rhinebeck heading toward Connecticut, eventually merging with the turnpike extending eastward from Market Street.

11. SOUTH STREET

SOUTH ST. (IN GENERAL)

12. EDWARD M. SMITH HOUSE

27 SOUTH ST.

Edward M. Smith, author of the 1881 Documentary History of Rhinebeck and the 1894 History of Kipsbergen, lived here while researching and writing extensively about the history of the Town of Rhinebeck. Much of our information about families who lived here during the Revolutionary War comes from Smith. (This is a private home. Please respect the privacy of the homeowner by remaining on the sidewalk while admiring this house and its history.)

Riley Delamater, the original owner of this house, served in the 1850s as the first principal of the first public school in the Village of Rhinebeck, located on Oak Street. During WWII, his grandson Walter would rise to the rank of Major General in the NY National Guard. Later, in his role as Most Eminent Sir Knight Walter Delamater, he served as the Grand Master in the US of the Knights Templar, a fraternal order affiliated with Freemasonry. (This is a private home. Please respect the privacy of the homeowner by remaining on the sidewalk while admiring this house and its history.)

13. DELAMATER HOUSE

12 CENTER ST.

14. RHINEBECK TOWN HALL

80 EAST MARKET ST.

Rhinebeck Town Hall was built through the efforts of Franklin D. Roosevelt with WPA funds in 1939. The offices of many town officials are here, and it serves as an important public meeting place for the citizens of Rhinebeck. The earlier town hall was located on Mill Street. It was torn down to make way for today’s post office.

15. STALEY REAL ESTATE

58-60 EAST MARKET ST.

This circa 1810 building is typical of buildings from the early Revolutionary period. Today serving as both as real estate and law offices, the house is said to have been owned by Peter Livingston and John Drury, first village judge.

16. SCHAAD BAKERY

55 EAST MARKET ST.

Schaad Bakery is an early Federal house, built about 1795. A barber, Nicholas Drury, owned it in 1867. Jacob Schaad lived there in 1876, and it remained in the Schaad family well into the 20th century. Currently a Thai restaurant, it previously housed a travel agency.

17. UNITED METHODIST CHURCH

83 EAST MARKET ST.

The United Methodist Church, second oldest in the Village, built here in 1822, burned in 1899 and was replaced by this brick building. Many valuable early records were lost in the fire. A tall memorial stone at the rear of the church honors the Reverend Freeborn Garretson, one of the founders of Methodism in America. 

18. CHURCH OF THE GOOD SHEPHERD

94 EAST MARKET ST.

The Church of the Good Shepherd was initially built as an Episcopal church in 1852, by architect George Veitch on land given by Rutsen Suckley. It became the current Catholic Church in 1901 when the Episcopalians built a new church on Montgomery Street (refer to item 28, Church of the Messiah, below) and sold this earlier church to the Catholic congregation.

19. THE PULTZ HOUSE

97 EAST MARKET ST.

The Pultz House was built in 1795, prior to the completion of the Salisbury Turnpike (East Market Street) as a through street. The house served as the home of Peter Pultz, owner of the Pultz Tavern at 104 East Market Street, where an historic marker provides more detail. (This is a private home. Please respect the privacy of the homeowner by remaining on the sidewalk while admiring this house and its history.)

20. STEPHEN MCCARTY HOUSE

110 EAST MARKET ST.

The Stephen McCarty house was once a tavern. A builder of Greek Revival houses in the town, he embellished this circa 1810 house with a portico imitating the Parthenon. In addition to his work as a craftsman and builder, McCarty was elected and served as the assessor for the Village. (This is a private home. Please respect the privacy of the homeowner by remaining on the sidewalk while admiring this house and its history.)

21. MONTGOMERY HOUSE

77 LIVINGSTON ST.

Montgomery House is named after General Richard Montgomery, who was married to Janet Livingston, eldest daughter of Judge Robert Livingston and granddaughter of landholder Henry Beekman. They lived in this house (when it was located on Montgomery Street) after their marriage in 1773. This is the Chapter House for the Daughters of the American Revolution (DAR). George Washington asked Richard to become a general in the Revolutionary army. He became the first general killed in the Revolutionary War when he was shot leading his army, attacking Quebec, attempting to secure Canada for the American cause. His widow soon completed Grasmere, a mansion south of the village at 29 Mill Road, where she would live for 27 years, and for her later years built and eventually moved to the palatial 55 Montgomery Place, overlooking the Hudson River in Barrytown.

22. THE O'BRIEN HOUSE

46 LIVINGSTON ST.

The O'Brien House, built by Henry Latson circa 1875, was designed in the second Empire Style by Gilbert Croff, a Saratoga architect and was the first house in the Village to use gas lighting. John O’Brien and his father-in-law, Albert Rider, were builders of canals and railroads, including the Central New England Railroad that ran from Rhinecliff to Hartford. (This is a private home. Please respect the privacy of the homeowner by remaining on the sidewalk while admiring this house and its history.)

23. THE THIRD LUTHERAN CHURCH

31 LIVINGSTON ST.

The Third Lutheran Church, built in 1842, possibly by Stephen McCarty, burned in 1909 and was rebuilt soon after in its current Greek Revival style. It is called the Third Lutheran Church because there were two other earlier Lutheran churches located elsewhere in the town of Rhinebeck. Many of the original Palatine settlers were Lutheran, from the Rhine area of what is now Germany. Beekman settled 35 Palatine families on his land by 1718. The town’s name, Rhinebeck, memorializes the river and the patentee, Rhine + Beek. 

24. THE DEGARMO INSTITUTE

29 LIVINGSTON ST.

No longer standing, the DeGarmo Institute was once an important private school, initially known as the Rhinebeck Academy when founded in 1860 and moved here by Professor James DeGarmo in 1871. It continued here until he moved the school to Fishkill in 1890, at which time this structure converted to an inn. Today the property is part of the adjacent Lutheran church.  (This is a private home. Please respect the privacy of the homeowner by remaining on the sidewalk while admiring this house and its history.)

25. THOMAS THOMPSON HOUSE

23 LIVINGSTON ST.

The Thomas Thompson House was initially built in 1843 as a Lutheran parsonage. A Boston financer and humanitarian who had visited Rhinebeck summers starting in 1867 wanted a rest home for the use of poor seamstresses. He left an inheritance that was used to convert this house for that purpose in 1901. It later became Rhinebeck’s first hospital. His generosity led later to the building of Northern Dutchess Hospital and to the support of many other non-profit organizations in Rhinebeck. (This is a private home. Please respect the privacy of the homeowner by remaining on the sidewalk while admiring this house and its history.)

26. THOMPSON-DRURY HOUSE

12 LIVINGSTON ST.

In the basement of this private residence, tunnels were found suggesting their use as an Underground Railroad site, perhaps part of a network of similar hiding places used before the Civil War to help slaves escaping their owners in the South find refuge further north in Canada. (This is a private home. Please respect the privacy of the homeowner by remaining on the sidewalk while admiring this house and its history.)

27. THE BAPTIST CHURCH

6426 MONTGOMERY ST.

The Baptist Church started soon after the Revolution in Rhinebeck. Robert Scott had moved here in 1796; by 1821 he had established a school and the church, members meeting in his home on South Street and elsewhere before eventually moving here to worship. The church initially consisted of a small chapel occupying the north part of this site, on land given by Mrs. Janet Montgomery in 1823. State Senator William Kelly, a Baptist, gave the church additional land and funds to expand further, and by 1890 it had added the large Queen Anne Victorian style addition that occupies the southern part of this corner lot. The building became a restaurant after the congregation moved to a new building on Astor Drive.

28. CHURCH OF THE MESSIAH

6436 MONTGOMERY ST.

The Episcopal Church of the Messiah was built in 1897 and has been called the ‘Millionaire’s Church.’ It was built through the generosity of John Jacob Astor, US Vice President Levi P. Morton, the Delanos, the Suckleys and the Wainwrights. It contains very beautiful Tiffany stained glass windows and a large pipe organ. The current Catholic Church of the Good Shepherd served initially from 1867 to 1897 as Rhinebeck’s Episcopal Church. In 1914 Reverend Little organized The Choristers School, for boys between seven and fifteen, famous throughout the region. Vestry records tell us Episcopal services in Rhinebeck go back as far as 1831, held in Methodist or Baptist Churches until they had their own building.

29. TAMMANY HALL

6443 MONTGOMERY ST.

Tammany Hall, no longer standing, was the contemporary name for an older inn on the same site, Kip’s Tavern. It operated as a stagecoach inn that served travelers between New York and Albany. Aaron Burr and other prominent men of his period associated with the New York City Anti-Federalist political party are said to have met here, hence the name. Tradition also says that Burr used the tavern as his headquarters during his campaign for governor in 1804, that he stayed there just before his duel with Alexander Hamilton, that he returned there after the duel. We do know as a fact that during the Revolutionary War, the building was owned by a gunsmith. Since the 1930s, the site has remained in the same family as an auto dealership.

30. OAK STREET

OAK ST. (GENERAL)

Freed slaves lived here in the early days, creating a village within a village. Note the general architecture of the area. The house at 16 Oak Street was built in 1844 and served as a one-room schoolhouse until 1860.  (This is a private home. Please respect the privacy of the homeowner by remaining on the sidewalk while admiring this house and its history.)

31. FIREHOUSE

18-20 WEST MARKET ST.

The firehouse was built about 1858 and housed a hand-pumper, “Pocahontas,” which helped save the commercial core of Rhinebeck in 1864 when a fire destroyed much of the south side of East Market Street. The second floor of the firehouse served for many years as the gathering place for community meetings, as the site for theatric performances, and as Rhinebeck’s first movie theater. The upper part of the arch on the portion of the building closest to the street served as the entrance bay for Pocahontas. When it’s not used for parades, "Pokie," as she was affectionately referred to by the firemen, is on display at the Dutchess County Fairgrounds. The former firehouse currently houses a spa and a beauty salon.

FURTHER REFERENCES

Dows, Olin, et al. Murals in the Rhinebeck Post Office. Rhinebeck, 1940.

Kelly, Nancy V. A Brief History of Rhinebeck. New York, 2001.

Kelly, Nancy V. Rhinebeck's Historic Architecture. Charleston, 2009.

Morse, Howard H. Historic Old Rhinebeck, Echoes of Two Centuries. Rhinebeck, 1908.

Plumb, Brian & Matthew. Rhinebeck's Historic Beekman Arms. Charleston, 2014.

Shelton, Hal T. General Richard Montgomery and the American Revolution. New York, 1994.

Smith, Edward M. Documentary History of Rhinebeck, in Dutchess County, NY. Rhinebeck, 1881.

Tietjen, Sari. Rhinebeck, Portrait of a Town. Rhinebeck, 1990.