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Hudson Valley Explorer for lovers of Nature, Culinary, and Culture

I Love NY

Start: NYC

Finish: Hudson Valley

Duration: 5 Days

Day 1

New York City

However long you decide to stay in New York City, you will find an abundance of activities to see and do. We suggest venturing out of the City to explore the stunning Hudson Valley. Enjoy an abundance of cultural, culinary, natural, and historical highlights not to be missed, as well as magnificent wineries, breweries and distilleries.

Hudson Valley

Day 2


Get away to the heart of the Hudson Valley for an abundance of enriching experiences. You’ll encounter the landscapes that inspired the country’s first arts movement, the motherland of American winemaking, the home of a beloved U.S. President, a vibrant farm fresh food scene, the arena for a revolution, and the place where aristocratic families established lavish estates.

Start in NYC and drive to Poughkeepsie. Travel along the banks of the majestic Hudson River offering beautiful views through the Highlands to the stunning natural beauty of the Hudson Valley.

First stop: Walkway Over the Hudson, the world’s longest elevated pedestrian bridge. Walk or bike the 2km long historic bridge which towers 65 meters above the Hudson River for unprecedented views and connects to 32km of rail trail. Find out more on the Walkway website.

Treat yourself to a meal at The Culinary Institute of America, the world’s premier culinary college. With an elite line up of world-renowned master chef alum, this "CIA" trains students from over 30 countries to be the world’s future chefs. Experience the ultimate in fine dining in public restaurant classroom settings. Enhance your visit with a behind-the-scenes student guided tour of the campus. Stay overnight in Poughkeepsie.

Day 3

A Day in Hyde Park

This is the birthplace of President Franklin D. Roosevelt, the only U.S. president elected to four terms. FDR was paralyzed by polio at age 39. He led the country out of the Great Depression, guided America through WWII, and is credited with conceiving of the United Nations. His home is open for tours and a highlight to his estate is the FDR Presidential Library & Museum. The museum is the first and only presidential library used by a sitting president and the interactive exhibits take you back in time to a pivotal moment in American and world history.

Val-Kill is the only National Historic Site dedicated to a First Lady. Eleanor Roosevelt was an activist, columnist, and co-authored "The Universal Declaration of Human Rights" at the United Nations. Guided tours invite you into the private life of one of the world’s most influential women.

The Vanderbilt Mansion National Historic Site is FDR’s neighbour to the north. The estate is a National Park located on the Hudson River with a formal Italianate garden and an impressive “Millionaire View”. The Gilded Age mansion is one of several gorgeous homes as part of "The Great Estates" available for guided tours in Dutchess County. Stay overnight in Overnight in Rhinebeck.

Vanderbilt Mansion National Historc Site

Day 4

Rhinebeck & Tivoli

Enjoy a variety of dining options in Rhinebeck, all within a walkable four-block radius. The intimate village also has boutique and antique shops, cafes and bars; all in beautiful historic buildings. Nearby is the Dutchess County Fairgounds which hosts weekend festivals and events from June through October.

Take to the skies in an open-air biplane at Old Rhinebeck Aerodrome. Home to one of the most impressive collections of early aviation, you can ride in a biplane any day of the week from mid-May through October. Visit a weekend airshow showcasing up to twenty flight-ready vintage aircraft at any given time from mid-June through October. CNN Travel released a great video on this!

Farm-to-table dining is a way of life in the Hudson Valley. Known as the country’s first wine region, you can tour and taste your way through wineries, distilleries, breweries and cideries along the Dutchess Craft Beverage Trail

Tivoli may be tiny but it’s the ideal Americana setting filled with specialty shops, art galleries, restaurants, bars, and the art inspired Hotel Tivoli is filled with an eclectic collection of furniture, lighting and art. The hotel restaurant features a Mediterranean inspired menu and inventive cocktails.

For live entertainment, venture over to nearby Bard College to encounter the spectacular Fisher Center designed by architect Frank Gehry. You’ll find world-class entertainment here year-round and an annual highlight, the SummerScape Festival, featuring eight weeks of opera, theatre, cabaret, film, music and dance. Stay overnight in Tivoli.

Day 5

Beacon is for art lovers

This Bohemian-style arts community is a popular destination with its expansive main street of art galleries, cafes, breweries, distilleries and specialty shops.

Dia: Beacon is a 300,000 square foot(27,870 sqm) museum which is a former box factory where you’ll experience large scale works by renowned contemporary artists dating back to the 1960s.

The natural scenery of the Hudson Valley with its Hudson River views along a backdrop of the nearby Catskill Mountains inspires everyone to get outdoors. Hiking, biking, kayaking and paddle boarding are all part of a visit to the scenic valley.

The park trails are extensive; each offering their unique views, and some connect to the famed Appalachian Trail. If you’re up for an easy stroll, there are multiple gardens including Innisfree Garden noted as one of the world’s ten best gardens.

Dia Beacon Museum

Return your car back to Poughkeepsie or continue on to discover more of upstate New York.

*The content and images in this top drive have been provided by I Love NY.

I Love NY Top Drive

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