October conjures up fall excursions to go apple picking, historic house hunting, and foliage spotting, and the Hudson Valley promises all of that with stunning scenery to spare. But where to go in the Hudson Valley can be a conundrum, as the region cuts a wide swath through New York State, stretching from Westchester County to Albany. Dutchess County, located within an hour north of New York City is the perfect escape for distinctive adventures you won’t easily find elsewhere in the Hudson Valley or upstate New York.
Scottish-style castles. Salt caves. Frank Gehry postmodern architecture. Picasso works on a quiet college campus. The world’s longest elevated pedestrian bridge. These are not the places you’d expect to see while visiting the Hudson Valley. Yet, they’re all in Dutchess County, along with other intriguing sites.
Here are ten in Dutchess County worth seeking out on your next upstate weekend getaway.
1. Bannerman Castle
Bannerman Castle
As you approach the town of Beacon by Metro North, it is hard to miss the decaying castle structures rising up from an island in the Hudson River. Though it could be mistaken for a crumbling citadel-inspired mansion, Bannerman Castle was actually built by Scottish-American entrepreneur Francis Bannerman as warehouses for his business “Bannerman’s,” a catalog business for war surplus (including munitions and large artillery). Originally based in Brooklyn and later Manhattan, Bannerman’s was forced to relocate when it procured a large stash from the Spanish American War, much of which was too dangerous to have within city limits. This proved wise, as the the powerhouse exploded in 1920 sending debris all the way across the Hudson and blowing out some of the warehouse windows.
The Bannerman Castle Trust has been working for many years to preserve the structures on the island, which include the main warehouse structure, a residence, and a breakwater system. You can take tours of Bannerman Island from May to October.
Wethersfield is a 1,200 acre estate that sits at 1,200 feet above sea level, the highest point in the region, offering views to the Catskills and the Berkshires. A Georgian-style colonial brick house and formal gardens at Wethersfield welcome visitors, to the estate, which is now run by the non-profit Wethersfield Foundation. The last owner of the estate, Chauncey Devereux Stillman, the grandson of the president of the financial firm that became Citigroup, formed the Wethersfield Foundation at around thirty years old in 1937, a testament to his foresight on how the property could be offered for the public to enjoy in the future. He would live until 1989, after which the Wethersfield Estate was opened to the public.
The architectural critic Henry Hope Reed called the three acre formal garden “the finest classical garden in the United States built in the second half of the twentieth century.” An additional 7-acre “Wilderness Garden” contrasts the formal garden. The estate also contains an impressive collection of painting, furniture and sculpture.
A carriage house contains 22 historic carriages, acquired and restored by Stillman, which were used for daily rides on the estate’s twenty miles of carriage trails. The farm at Wethersfield, which is still active, is considered “one of the first farms in the county to practice soil and water conservation” according to the Wethersfield website.
The horse, carriage, and hiking trails are open from mid-April to mid-November, while the house museum and gardens are open from June to September.
The Wethersfield Estate is located at 257 Pugsley Hill Road, Amenia NY, 12501, ten miles northeast of Millbrook.
3. Frank Gehry’s Richard B. Fisher Center for the Performing Arts at Bard College
Photo courtesy Dutchess Tourism
There’s a Frank Gehry building tucked inside Bard College, with the recognizable curved steel facades that are found at some the architect’s most notable commissions, the Guggenheim Museum in Bilbao and the Walt Disney Music Hall in Los Angeles. The Richard B. Fisher Center at Bard College is a 107,000 square foot state of the art performing arts center with two halls, one that seats 800 and another that seats 200, along with dance and theater studios. Gehry worked in partnership with master acoustician Yasuhisa Toyota, who also perfected the sound at the Walt Disney Music Hall.
Speaking about the form and function of the building, Gehry has said, “The front façade of the building can be interpreted as a theatrical mask that covers the raw face of the performance space.” The spaces themselves are highly adaptable and have been home to a wide range of performances from opera, dance, to rock concerts to chamber music.
Check out all the upcoming events at the Fisher Center here. Bard College is located in Annandale-on-Hudson.
Fans of flight history shouldn’t miss a visit to the Old Rhinebeck Aerodrome, a passion project that has been in operation more than sixty years, founded by Coel Palen, who started with six defunct World War I airplanes and created the first flying museum of antique aircraft and replicas. There are now more than sixty historical airplanes, with flight shows every Saturday and Sunday. You can even take a bi-plane ride.
The Rhinebeck Aerodrome is open until daily from May 1 to October 31st. You can check out the full list of upcoming events here, which include a very fall-inspired Pumpkin Bombing Air Show all month long, where pumpkins are dropped in lieu of bombs, and an Oktoberfest celebration with food, beer and music on Saturday, October 6th.
The Rhinebeck Aerodrome is located at 9 Norton Road, Red Hook, NY 12571.
Did you know there is a fairy tale castle in Dutchess County? Right next door to the Millbrook Winery, a popular location for weddings and events, is Wing’s Castle, built by artists Peter and Toni Wing. Peter grew up on the dairy farm that became the Millbrook Winery, and him and his wife began building Wing Castle in the 1970s. The process, the couple say, is still unfinished but there is much to see here nonetheless. The castle is constructed of different sized stones and brick – in fact 80% of the castle is made of recycled materials – with turrets to spare. The interior is in a Tudor style with exposed wood beams and arched vault hallways, decorated with medieval furniture and accoutrements. The moat of the castle serves as the swimming pool and even goes beneath the building itself!
The castle operates as a bed and breakfast, and the rooms have enticing names like The Tower, the Dungeon, and The Annex Suite. There’s also a separate Tudor-style cottage available.
The Clermont State Historic Site is located right on the Hudson River, the former mansion and estate of Robert Livingston, the son of the Revolutionary War figure of the same name. The elder Lord Livingston once had 160,000 acres of land, and gave his second son Robert 13,000 acres which became the Claremont estate. The first mansion was built in 1740, but was burnt to the ground during the Revolutionary War by the British, in retribution for the family’s support of the American side of the war. Livingston’s wife, Margaret Beekman Livingston, rebuilt the house during the war.
The estate remained in the family until 1962, when it was offered to New York State as a historic site. The home is surrounded by 500 acres that belongs to the historic site. The home and visitor center is open until late December but the gardens, grounds and trails are open all year round. Upcoming events include Candlelight Ghost Tours and an Autumn Bird Walk.
The Clermont State Historic Site is located at 87 Clermont Avenue, Germantown, NY 12526.
Located in Millbrook, the Innisfree Garden is a masterpiece of art, a multi-decade passion project by Walter Beck, his wife the heiress Marion Burt Beck, and Lester Collins, a Harvard graduate who would later become Dean of Harvard Graduate School of Design’s landscape architecture department. Beck was initially inspired by the 8th-century Chinese garden designer, poet and painter Wang Wei. According to the Innisfree Garden website, “Beck observed that Wang created carefully defined, inwardly focused gardens and garden vignettes within a larger, naturalistic landscape. Wang’s place-making technique — christened ‘cup gardens,’ by Beck — influenced centuries of Chinese and Japanese garden design. It is also the principal design motif in the Innisfree landscape.
Collins would write in his book, Innisfree: An American Garden, published posthumously in 1994, “The garden, like a stage set, is there in its entirety, its overall design revealed in a glance. The traditional Chinese garden is usually designed so that a view of the whole is impossible. [It] requires a stroll over serpentine, seemingly aimless arteries. The observer walks into a series of episodes, like Alice through the looking glass.” The garden within a garden concept allows for an infinite number of micro-experiences at multiple scales, which connect but can exist independently from one another.
The garden was open to the public in 1960, following the death of Marion Beck, and Collins was instrumental in transforming the private garden into a public one.
The Innisfree Garden is located at 362 Tyrrel Road, Millbrook, NY 12545.
Locust Grove is the 200-acre Poughkeepsie estate of Samuel B. Morse, a painter and inventor of the telegraph and other creations in the 19th century. The Italianate mansion was designed by Alexander Jackson Davis, who designed New York City’s Federal Hall, the Gilded Age mansion at Lyndhurst (the home of Jay Gould and his family), and many more commissions. After Morse’s death, William and Martha Young, a wealthy couple from Poughkeepsie rented and later purchased the property and expanded the home. Their daughter created a foundation to open the home and showcase the family’s extensive art collection and archives, to the public.
In addition to the mansion, you can walk around the gardens, walking paths, or visit the Locust Lawn Farm (now a nature preserve with a beautiful Federal-style mansion). Locust Grove hosts a series of programs and events throughout the year.
The Locust Grove Estate is located at 2683 South Road, Poughkeepsie, NY 12601
Imagine over a hundred acres of rolling hills and meadows, inspired by the poets from the Hudson Valley, and designed with a European-influenced Romanticism in mind and you’ll have the Poet’s Walk, located right in Dutchess County just north of Rhinebeck. The Poet’s Walk, a shaded 2-mile trail along a stream, goes back to the mid-19th century – part of a 120-acre commission by neighboring Astor and Delano family estates. German-born landscape architect Hans Jacob Ehlers dotted the scenery with rustic pavilions, wooden benches, footbridges and a wide range of plantings, of which today there are over 140 types. It bears more than a passing resemblance the Shire from Lord of the Rings, and local legend has it that Washington Irving conjured up the character Rip Van Winkle here. Today, The Poet’s Walk is owned and operated by the organization Scenic Hudson.
The Poet’s Walk is open year round and can be accessed through the entrance at
Vassar College in Poughkeepsie was the first college or university in the United States to include an art museum in its original plan. The Frances Lehman Loeb Art Center is a combination of two buildings, a new museum designed by architect Cesar Pelli and a Gothic building, the Taylor-Van Ingen Hall, that was part of the original campus. A lush sculpture garden completes the center. In addition to galleries, the center also has storage for the 21,000-piece strong art collection which includes important works across multiple time periods from Europe, America
The Frances Lehman Loeb Art Center is located at 124 Raymond Ave, Poughkeepsie, NY 12603
Michelle is the founder of Untapped New York and the author of The Art Spy (HarperOne, forthcoming) Secret Brooklyn, Secret New York Hidden Bars & Restaurants, and Broadway. michelleyoungwriter.com
