Spend five days near the Hudson River, in the northwest section of Dutchess County, and you’ll be rewarded with a look back in history, a taste of culinary excellence, and the sound of the great outdoors. This itinerary brings you to Annandale-on-Hudson, Hyde Park, Rhinebeck, Red Hook, and Staatsburg. Please check individual site's website for the most up-to-date hours of operation and COVID restrictions.

S = Seasonal attraction or activity
SE = Open during scheduled events

Day 1: Hyde Park

Home of Franklin D. Roosevelt National Historic Site
Told from many angles, the story of the Roosevelt presidency, from the Great Depression through the New Deal years and World War II, is presented here in vivid and tangible fashion. Spend the morning touring the Springwood estate, FDR’s home, as well as the Franklin D. Roosevelt Presidential Library and Museum.

Vanderbilt Mansion National Historic Site
Frederick Vanderbilt was not the only wealthy industrialist to build a country palace. But this striking estate, his home from 1896 to 1938, remains one of the best examples from the Gilded Age. Your visit should include a stroll through the formal gardens and hiking trails for spectacular views of the Hudson River.

Dinner at The Culinary Institute of America
All you need to dine at world’s premier culinary college is reservations. Your dinner at American Bounty, Bocuse, or Ristorante Caterina de’ Medici, could be created by the next Charlie Palmer or Roy Yamaguchi. Founded in 1946, the CIA has trained culinary icons including Grant Achatz, Anthony Bourdain, and Cat Cora.

Day 2: Staatsburg and Rhinebeck

Staatsburgh State Historic Site (S)
Get a glimpse of the Gilded Age (1876 - 1917) when you tour the elegant country home of Ogden Mills and his wife Ruth Livingston Mills. Don’t miss the special themed tours and Gilded Age Tea & Talk programs! This 65-room Beaux- Arts mansion—furnished in the styles of Louis XIV, Louis XV and Louis XVI—sits on 192 acres on the Hudson River in Mills-Norrie State Park.

Wilderstein Historic Site (S)
On to a view of Victorian architecture. This exquisite Queen Anne mansion, with its Calvert Vaux designed landscape, was the home of Margaret (Daisy) Suckley, whose extraordinarily close relationship with Franklin Delano Roosevelt has been well-chronicled and is the subject of much interest.

Dinner at the Tavern at the Beekman Arms
To enjoy a meal at this Rhinebeck institution is to dine in a location that has been warmly serving guests since 1766. The Beekman Arms & Delamater Inn is America’s oldest continuously operated hotel, and its restaurant serves lunch, dinner, and Sunday brunch.

Day 3: Rhinebeck

Village of Rhinebeck
You could spend hours exploring this sophisticated, fourcorners town, thanks to a wealth of shops, restaurants, art galleries and theaters. More than 40 specialty shops and 20 eateries are nestled in and around the historic, tree-lined village streets. Park along Montgomery, and be sure to hit Market, Garden, and Mill streets, as well.

Old Rhinebeck Aerodrome (S)
This is more than just a museum housing one of the world’s largest collections of World War I and Golden Age aircraft and antique automobiles. It’s a stage for amazing weekend airshows, and a place where you can don a helmet and goggles for a ride over the Hudson River in the open cockpit of a 1929 New Standard D-25.

Ferncliff Forest, Rhinebeck
For a more serene experience, lace up your walking shoes or hiking boots and hit the four miles of trails through 200 acres of old growth forest which once belonged to the Astor family. You’ll see the remains of hand-dug wells and foundations, then you can stop by Mount Rutsen pond. For extraordinary Hudson Valley views, climb the fire tower!

Day 4: Red Hook and Annandale-on-Hudson

Village of Red Hook
Enjoy a morning with a “Main Street America” feel in this walkable village, where you’re never far from a historic building, shop, or eatery. Pick a sidewalk—along Route 9 or Market Street, maybe? —and get caught up in the local rural heritage and vibrant community life.

Bard College (SE)
Founded in 1860, this prestigious college of the liberal arts and sciences opens its world class cultural offerings to the general public; most notably the Fisher Center for the Performing Arts, a monumental space designed architect Frank Gehry. From September through December, watch for musical concerts, dance performances, theatrical events, intimate evenings with theater and performance artists, and more. The SummerScape programming includes seven weeks of opera, music, theater, dance, film, and cabaret, with the Bard Music Festival at the center of the festivities.

The visual arts are celebrated on campus at the CCS Bard Hessel Museum. The facility’s rich permanent art collection, along with temporary exhibits from masters such as Sol LeWitt, Robert Mapplethorpe, and William Copley, make this one of the world’s most forward thinking environments for the research and practice of contemporary art and curatorship.

Day 5: Annandale-on-Hudson and Red Hook

Montgomery Place
When you visit this Hudson Valley estate, you see American history through an environmental lens. The 380-acre property is best known as a landscape influenced by the great Andrew Jackson Downing, with woodland trails laid out more than 100 years ago, and lush gardens designed in the early 20th century. Grounds open year-round; mansion tours available in season.

Poet’s Walk Park
For a different look at the local landscape—its beauty inspired the creation of the Hudson River school of painting, after all—take a walk in this 120-acre riverside park. Nearly two miles of trails meander through meadows and woods. Legend has it that Washington Irving came up with the idea for “Rip Van Winkle” here while gazing upon the Catskill Mountains.