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A Tourist Guide to Rhinebeck, New York

1. Introduction and History 

Located on the east side of the Hudson River in Dutchess County some 100 miles north of Manhattan, Rhinebeck, accessed by the Taconic State Parkway, Route 9, Route 9W, and the New York State Thruway, is both a picturesque and intensely historic village.  It itself is part of the Hudson River Valley National Historic Area which was established in 1996 by Congress to recognize, preserve, protect, and interpret the nationally significant history and resources of the valley for the benefit of the nation, and stretches from Yonkers to Albany.

Founded in 1686 when Dutchmen Gerrit Artsen, Arie Roosa, Jan Elting, and Henrick Kip exchanged 2,200 acres of local land with six Indians of the Esopus (Kingston) and Sopaseo (Rhinebeck) tribes, it was initially designated “Kipsbergen.”  In 1713, Judge Henry Beekman referred to these land holdings as “Ryn Beck” for the first time.

One of the country’s largest historic districts with 437 sites listed on the National Historic Register, the nucleic Village of Rhinebeck and the larger, surrounding Town of Rhinebeck, encompass half of the 16-mile stretch which includes the 30 contiguous riverfront estates associated with the landed aristocracy of the region during the 18th, 19th, and early 20th centuries.

Often dubbed a “picturesque village” and the “jewel of the Hudson,” it offers many walking-proximity attractions, such as antique shops, art galleries, bed-and-breakfasts, inns, and restaurants, usually housed in historic buildings.         

Signature and stalwart of the village is the Beekman Arms, America’s oldest, continuously operating inn listed on the National Register of Historic Places.  Tracing its origins to 1766 when Arent Traphagen relocated his father’s successful Bogardos structure of stone and sturdy timber– so constructed to protect it against Indian attacks–to the crossroads of the recently designated Ryn Beck village, it ultimately served as a Mecca of revolutionaries, often hosting the likes of George Washington, Benedict Arnold, and Alexander Hamilton.  When the British burned then-state capital Kingston, located across the Hudson, the townspeople sought refuge here.

Purchased by Asa Potter in 1802, it subsequently served multiple roles, including town hall, theater, post office, and newspaper post.

Renovated, expanded, and renamed its current “Beekman Arms” moniker by secondary owner Tracy Durs, it served as inspiration for Thomas Wolfe’s novel, Of Time and the River, after frequent visits here, and Franklin Delano Roosevelt, hailing from nearby Hyde Park, initiated all four of his successful gubernatorial and presidential campaigns form its very front porch.

The significantly larger complex provides venues for sightseeing, dining, and accommodation, amidst a preserved, colonial atmosphere.

The Tavern at Beekman Arms, located on the ground floor, is decorated with dark wood trim, a huge brick fireplace, and wide plank floors, and is subdivided into the Colonial Tap Room, a garden greenhouse, and several separate dining areas.

The upper floors contain the original inn’s meticulously restored and elegantly appointed 1766 rooms, although accommodation is available in numerous affiliated structures.  Amid exposed brick walls and high ceilings, for instance, guests can stay in the village’s original firehouse, while the Townsend House, which opened in 2004, features the design and architecture influenced by Rhinebeck’s other historical structures.  The Guest House, located behind the main inn, offers lower-cost, motel-style rooms.

The Delameter Inn, designed in 1844 by Alexander Jackson Davis and an example of American Carpenter Gothic architecture, is one block north of the Beekman Arms, and is part of a seven-guesthouse complex which surrounds a courtyard.  Many rooms feature fireplaces.

Rhinebeck itself offers many attractions.  The Dutchess County Fairgrounds, for instance, hosts events such as the Dutchess County Fair, the Rhinebeck Antiques Fair, the Crafts at Rhinebeck exhibition, and the Iroquos Festival, while the Center for Performing Arts at Rhinebeck offers live classical, drama, musical, and children’s performances showcasing local theater companies, although talent has also included national and international names.  Resembling an oversized barn to complement the surrounding rural landscape and to pay tribute to the origins of summer stock, it replaced the temporary tent under which seasonal performances had been given between 1994 and 1997, opening in July of the following year and becoming a year-round venue in 1999.

Several early-aviation and architecturally historic sights surround the immediate town, most of which offer exquisite views of the Hudson River and the Catskill Mountains beyond it.

2. Museum of Rhinebeck History

Located 3.5 miles north of the Village of Rhinebeck on Route 9, the Museum of Rhinebeck History, housed in the historic Quitman House, was founded in 1992 “to encourage understanding and appreciation of Rhinebeck history through the collection, preservation, exhibition, and interpretation of materials significant to Rhinebeck” by means of letters, books, journals, clothing, furniture, photographs, postcards, and artifacts.  Open from mid-June to October 31, it features two annual exhibits, previous ones of which have been entitled “The First Century,” “The Civil War,” “The Guilded Age,” “World War I,” “The Roosevelt Years,” “World War II,” and “Early Rhinebeck Industries,” among others.

The Quitman House, marking the area of the town’s first settlement, had been built in 1798 as a parsonage by the parishioners of the nearby Old Stone Church for the Reverend Frederick H. Quitman, who had served the Lutheran congregation for more than three decades.

Henry Beekman, who had settled 35 Palatine German families in the area in the early-1700s, had been given most of the land by royal grant, and the nascent community developed round a single log church until the 19th century, at which time commerce had taken root three miles south in the village designated “The Flatts.”

3. Wilderstein

Located two-and-a-half miles from the historic downtown district of Rhinebeck, Wilderstein, named after the petroglyph of a figure holding a peace pipe in his right hand and a tomahawk in his left in Suckley Cove, translates as “wild man’s stone” from the German, and had been a restrained Italianast villa when it had been built in 1852.  Home to three generations of the Suckley family, it had been significantly enlarged in 1888 with two upper floors, a tower, and a veranda, rendering it the elaborate Queen Anne-style mansion overlooking the Hudson River it is today.

The interior retains all of its original wall carvings, furniture, artwork, book collections, and stained glass from its 1888 expansion, and the ground floor, designed by Joseph Burr Tifany, features a dark, heavily-paneled foyer, a fireplace, a library, a dining room, a kitchen, and two living rooms.

Calvert Vaux and his son, hired in 1890 to design the outdoor landscape in Romantic style, had already had a long list of similar accomplishments, among them other Hudson River estates and Prospect Park and Central Park in New York, and had ordered 1,091 shrubs and 41 trees from a local Rhinebeck nursery for the Wilderstein project.  The area, greatly reduced from its original size, currently encompasses 40 acres and three miles of trails.

Margaret (Daisy) Suckley, a close friend of Franklin Delano Roosevelt and the last to survive, had ceded the mansion and its grounds to the Wilderstein Preservation in 1983, a not-for-profit educational institution.  Today, it is listed on the National Register of Historic Places.

4. Old Rhinebeck Aerodrome

Located on tiny, easily-missed Norton Road on the east side of the Hudson River not far from the village of Rhinebeck itself, Old Rhinebeck Aerodrome offers a time portal to the grass fields and fabric-covered aircraft which represent the first “sprout” of aviation a century ago.

Its own seed had been planted when Cole Palen, having earned his airframe and powerplant license form the now defunct Roosevelt Aviation School on Long Island, purchased six airplanes offered for sale by its museum in order to vacate the area for the pending Roosevelt Field Shopping Mall.

After storage in an abandoned chicken coop on the Palen farm in Rhinebeck, the six aircraft, which encompassed a 1917 SPAD XII, a 1918 Standard J-1, a 1914 Avro 504K, a 1918 Curtiss Jenny, a 1918 Sopwith Snipe 7F1, and a 1918 Aeromarine 39B, had formed his initial fleet and the “aerodrome” had been a 1,000-foot-long, rocky, swamp-drained clearing called a “runway” and a single crude building serving as a “hangar” on a patch of farmland he had subsequently purchased.  Additional aircraft acquisitions—and parts of them—had expanded the mostly biplane lineup, after considerable restoration and reconstruction.

Three metal, quonset hut-like hangars, built between 1963 and 1964 and located at the top of a small hill above the main dirt-and-grass parking lot, house Pioneer, World War I, and Lindbergh era aircraft today, across from a new museum facility and a small gift shop.  But the aerodrome itself, on the other side of Norton Road, is accessed by a wooden covered bridge which serves more than just an entrance to the grass field, but as the time portal itself to the barnstorming era of aviation, an historical dimension somehow arrested and preserved in time beyond its boundaries.

The hangers, as if ignorant of the calendar, proudly brave the winds, bearing such names as Albatros Werke, Royal Aircraft Factory Farnborough, A.V. Roe and Company, Ltd., and Fokker.  But it is the multitude of mono-, bi-, and triplanes which most fiercely wrestles with one’s present-time conception.

The current air show program, which runs from mid-June to mid-October, features the “History of Flight” show on Saturdays, with pioneer aircraft such as the Bleriot XI, the Curtiss D “Pusher,” and the Hanriot, while the “World War I” show on Sundays includes designs such as the Albatros, the Avro 504K, the Caudron G.III, the Curtiss JN-4D Jenny, the Fokker D.VII, the Fokker Dr.I, the Nieuport II, the Sopwith Camel, the SPAD VII, the Davis D1W, the de Havviland Tiger Moth, and the Great Lakes 2T-1R.  Biplane rides in four-passenger New Standard D-25s are given before and after the shows, while viewers can admire the fleet either in hangars or on the grass aerodrome while having lunch on outdoor picnic tables at the Aerodrome Canteen.

Audience volunteers, sporting Victorian, Edwardian, and 1920s dress, provide fashion shows after changing in the aerodrome’s single, track-mounted, red caboose, often transported past spectators in vintage vehicles such as a 1909 Renault, a 1916 Studebaker, and a 1914 Model T Speedster.  Period music completes the scene.

The air shows themselves, which feature only treetop-high sprints of the pioneer aircraft before immediate relandings on the grass, otherwise offer more dramatic maneuvers of the World War I and Lindbergh era designs, including aerobatics, dogfights, bomb raids, balloon bursts, parachutists, and “Delsey drives.”

5. Montgomery Place

Designed by Alexander Jackson Davis and nestled on a landscape influenced by Andrew Jackson Downing, Montgomery Place, located off of Route 9G in Annandale-on-Hudson, is a richly-ornamented, classical revival, architectural landmark, reflecting both Hudson Valley estate life and almost 200 years of family ownership and imprint.

Tracing its origins to 1802 when 59-year-old Janet Livingston Montgomery had purchased a 242-acre area to establish a commercial farm and construct a house called the “Chateau de Montgomery” to honor her husband, General Richard Montgomery, it first served as a base in which to live and work.

Poised at the end of a half-mile long alley of deciduous trees, the federal style, stuccoed fieldstone house became the center of orchards, gardens, nurseries, and greenhouses, and flowers and trees had been sent to her from exotic areas of the world, including magnolia, yellow jasmine, orange, and mangos from England and Italy in Europe and Antigua in the Caribbean.  The prosperous enterprise supplied seeds and fruit trees to local farmers.

Although the estate had been intended for General Montgomery’s heirs, their earlier deaths forced her to cede it to her youngest brother, Edward Livingston, whose public service career had encompassed positions as New York City Mayor, US Representative and Senator from Louisiana, Secretary of State, and Minister of Finance during the Andrew Jackson administration.

Louis Livingston, his widow, and Coralie Livingston Barton, his daughter, renamed the mansion “Montgomery Place,” using it as a summer domicile and extensively modifying its architectural and landscape features during a 40-year period.  The farm and pastureland, particularly, sported formal flower gardens and an ornate conservatory, and the estate’s aesthetics were enhanced with walking paths to the Saw Kill Stream, rustic benches, colorful fruit gardens, and an arboretum comprised of purple-leafed European beech, cucumber magnolia, red oak, sweetgum, Tuliptree, white oak, Sargent’s weeping hemlock, flowering dogwood, Amur Corktree, black locust, and Sycamore trees.  These 150-year-od monoliths of nature can still be enjoyed today during the walk from the Visitor’s Center and the actual mansion.

Based upon the style of Alexander Jackson Davis, then the greatest American architect of the romantic movement, the house itself was redesigned with porches, wings, and balustrades during a dual-phase process which commenced in 1842 and later in 1860, rendering it the classical revival example it is today.

Andrew Jackson Downing, then foremost landscape writer and co-owner of a nursery in Newburgh, New York, provided input concerning gardens, statuary, walking paths, and water features.

After a post-Civil War decline, during which time the property had been occupied by relatives, General John Ross Delafield, a Livingston descendent and New York attorney, inherited it, and his wife, Violetta White Delafield, herself a botanist, resurrected the landscape by introducing garden rooms for roses, herbs, and perennials, a wild garden with an artificial stream, and a hedged ellipse with a pool for aquatic plants.

In 1986, Delafield descendants conveyed title to Montgomery Place, its 424 acres of land, and a portion of the hamlet of Annandale, to Sleepy Hollow Restorations (later renamed Historic Hudson Valley) in order to ensure its restoration and preservation.  Now a National Historic Landmark, it reopened to the public two years later.

6. Bard College

Only a short distance further north and immediately off of Route 9G in Annandale-on-Hudson is Bard College.  A fusion of two historic estates, the liberal arts, residential campus, situated on more than 500 acres of fields and forested land bordering the river, features a complex of trails and walking paths through wooded areas, along the Saw Kill Stream, and down to the Hudson River, where the rising Catskill Mountains are visible.

Founded in 1860 by John Bard in association with the New York City leadership of the Episcopal Church and initially named St. Stephens College, it used part of Bard’s riverside estate, Annandale, and the Chapel of the Holy Innocents, both of which he donated, to teach a classic, preparatory curriculum for those intending to enter the seminary.

Transitioning to a broader, more secular institution in 1919, it incorporated both natural and social science courses in its curriculum for the first time, and a decade later served as an undergraduate school of Columbia University.  Increasingly focusing on liberal arts, it officially adopted the “Bard College” name in 1934 and ten years later became a coeducational institution, severing ties with Columbia.

By 1960, the very expanded curriculum included science, art, art history, sculpture, and anthropology, and attracted a significantly larger student and faculty base.  A film department was introduced.

Its first graduate program, the Milton Avery Graduate School of the Arts, was established in 1981, and, by the summer of 1990, the Bard Music Festival, created to provide a deeper appreciation of the repertory of reknowned composers, was introduced, focusing on the work and era of a different artist and showcased in the modern, metal-roofed, Frank O. Gehry-designed Richard B. Fisher Center for the Performing Arts in 2003.  The architecturally bold, innovative structure, offering tours during the day and chamber, orchestral, jazz music, drama, musical, dance, and opera performances by American and international artists during the evening, is subdivided into three venues.  The Sosnoff Theater, with an orchestra, parterre, and two balcony sections, features seating for 900, while the teaching Theater Two sports adjustable, bleacher-type seats and a semi-fly tower with a catwalk.  The Felicitas S. Thorne Dance Studio serves as a classroom and rehearsal hall.

7. Clermont State Historic Site

The 500-acre Clermont State Historic Site, north of the town of Tivoli and off of Route 9G, was the seat of the politically and socially prominent Livingston family whose seven generations shaped both the house and its grounds over a 230-year period.

The estate harks to 1728 when Robert Livingston, Jr. acquired 13,000 acres of land along the Hudson River from his father, the First Lord of Livingston Manor, who had owned the second largest tract of private land in colonial New York, and built a brick, Georgian-style mansion between 1730 and 1750, christening it with the French name for “clear mountain,” or “clermont,” after the Catskill peaks visible across from it.

When his only son, Robert P. Livingston, subsequently married Margaret Beekman, who herself had been heir to immense expanses of land, he considerably expanded the property’s boundaries.  Their own, and eldest, son, Robert. R. Livingston, Jr., was a prominent and highly influential figure who, as one of the Committee of Five, drafted the Declaration of Independence, served as the first US Minister of Foreign Affairs, specifically as Secretary of State, and Chancellor of New York, under whose title he gave oath of office to George Washington as the nation’s first president.

Because of the Livingston family’s involvement in fostering independence, British troops targeted and burned the mansion in the autumn of 1777, but Margaret Beekman Livingston, who had managed it, had it reconstructed during the three-year period between 1779 and 1782.

Developed for agricultural purposes, it was the site of experimental sheep breeding and yield-increasing crop methods, attracting national attention.

A more elaborate house, in an “H” configuration, had been constructed south of the original one in 1792, but was decimated by flames in 1909.

Serving as Thomas Jefferson’s Minister to France from 1801 to 1804, Chancellor Livingston negotiated the Louisiana Purchase in Paris, and later jointly designed the world’s first steamboat with Robert Fulton.  Making its inaugural voyage from New York to Albany in 1807, it reduced the journey by land to less than half the time and paved the way toward the Fulton Steamboat Company and the lucrative transport of passengers and cargo along the Hudson River.

After having been willed to the chancellor’s oldest daughter, the estate received considerable addition and modification, and in the 1920s, John Henry Livingston and his wife, Alice Delafield Clarkson Livingston, remodeled it in the Colonial Revival style.

Dwelling there between her husband’s death and the onslaught of the Second World War, she then moved to the gardener’s cottage, unable to maintain its costly upkeep, although it was usually opened during holidays and special occasions.

Deeded to New York State in 1967, it was subsequently designated a National Historic Landmark in 1973, and today appears as it did in the early 20th-century when it had been occupied by Mr. And Mrs. John Henry Livingston and their daughters, Honoria and Janet, the last two generations to have lived there.

A Visitor’s Center, located a short walk from the actual mansion, features a museum with a model of the first steamboat, a gift shop and bookstore, and an introductory film.

8. Conclusion

A visit to the Village and Town of Rhinebeck, along with its many significant sights, is an immersion into the historic inns, bed-and-breakfasts, antiques and artwork, architecturally-bold and barn-like theaters, vintage aviation, and earlier-century aristocratic estate life of the region, all with the azure backdrop of the Hudson River and the green silhouettes of the Catskill Mountains rising beyond it. 

About the Author

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