Scenic Hudson Valley

A 7-Day Road Trip — From Manhattan to Glenmere Mansion

New York City is a teeming metropolis, but it is also a gateway to the tranquil Hudson River Valley, with orchards, vineyards, fine restaurants and stately homes that have afforded escape to some of the great names in American history, including Rockefeller, Vanderbilt and Roosevelt. There are several delightful hotels that offer comfort and hospitality, if not always the last word in luxury.

Stretching 315 miles north from New York Harbor to its source in the Adirondacks, the Hudson saw its role as a trade artery magnified with the opening of the Erie Canal in 1825. This connected the river to the Great Lakes, ensuring that New York eclipsed Philadelphia as the largest city on the Eastern Seaboard. But the economic tide ebbed, and during the 20th century the Hudson Valley fell into decline. Fortunately, the past few years have seen a tremendous renewal spurred by relatively inexpensive real estate, a revived agricultural base — stimulated in part by the farmers markets of New York City — and the appeal of the river itself, now cleansed of industrial pollution.

Itinerary Highlights

Our itineraries are for your inspiration. Please contact a travel advisor to customize this itinerary to fit your needs.

  • Discover the Hudson Valley’s Rockefeller legacy
  • Dine at one of our Restaurants of the Year
  • Explore and taste the fresh produce of the Stone Barns Center for Food & Agriculture
  • Walk through the homes of some American greats
  • Sip delicious Hudson Valley wines along the Shawangunk Wine Trail

Trip Overview

Day 1 : Sleepy Hollow & Bedford
Discover pieces of Rockefeller's legacy along the Hudson.
Day 2 : Beacon
Shop and dine your way through the town of Beacon.
Day 3 : Poughkeepsie & Hyde Park
Explore the homes of American greats like Vanderbilt and Roosevelt.
Day 4 : Hudson
Walk Warren Street and visit the Hudson River School.
Day 5 : Milton
Taste the delicious wines of the Hudson Valley along the Shawangunk Wine Trail.
Day 6 : West Point & Chester
Tour West Point and relax at the lavish property of Glenmere.
Day 7 : Depart
Return to Manhattan.
.itinerary-cta-top

Day 1 : Sleepy Hollow & Bedford

Set off from Manhattan toward Westchester County. Stop at Kykuit, the Rockefeller estate in Sleepy Hollow, known for its architecture and gardens and also for the art collection assembled over several generations, with sculptures by Picasso, Henry Moore and Alexander Calder.

The area’s Rockefeller legacy also includes the Union Church of Pocantico Hills, with stained-glass windows by Chagall and Matisse, and the Stone Barns Center for Food & Agriculture, a nonprofit farm that runs programs on sustainability. 

If time allows, be sure to visit Sunnyside, the home of Washington Irving, America’s first great literary success.

Where to Stay

Bedford Post Inn

Dining & Drinks

Blue Hill at Stone Barns The Barn The Inn at Pound Ridge by Jean-Georges
Rockefeller Estate -
Berkshire pork chop at The Inn at Pound Ridge 
by Jean-Georges -

Day 2 : Beacon

From Bedford, drive northwest for an hour to the town of Beacon. Be sure to catch a glimpse of the river flowing grandly between tree-crested hills on your route. 

Beacon once boasted a strong manufacturing economy, which left a legacy of substantial real estate. The town’s turnaround began in 2003, when the Dia Art Foundation purchased a building where Nabisco had once printed boxes for its cookies and crackers. Dia:Beacon proved to be a draw for urbanites in search of affordable getaways, and the town is now full of shops, galleries and restaurants.

Where to Stay

The Roundhouse at Beacon Falls

Dining & Drinks

Ziatun Dogwood
An old-fashioned at The Roundhouse at Beacon Falls
An old-fashioned at The Roundhouse at Beacon Falls - Photo by Hideaway Report editor

Day 3 : Poughkeepsie & Hyde Park

Heading north, skip the main highways and head toward Poughkeepsie on the scenic local roads. At Poughkeepsie, an old railroad bridge has been transformed into a popular footbridge, the Walkway, which spans the Hudson — more than a mile wide at this point — and affords magnificent views from a height of 212 feet.

Twenty-three miles north of Beacon, go to Hyde Park, site of the 
Home of Franklin D. Roosevelt and his Presidential Library & Museum, the Vanderbilt Mansion and The Culinary Institute of America, with multiple restaurants open to the public.


Stay the night at the secret (and rustic) farm-to-table hotel, The Duchess, in Straatsburg.

Home of Franklin D. Roosevelt in Hyde Park -
The Culinary Institute of America

Day 4 : Hudson

Press on to the town of Hudson, a once-dispiriting place that is now the poster child for renewal. Though 120 miles from the Atlantic, Hudson became an active whaling port after Nantucket seamen, fearful of retribution following the Revolutionary War, relocated there for safety. The small town became a major center for shipbuilding and whale oil processing. 

Today, the main artery, Warren Street, displays a wealth of restored Greek Revival and Federalist townhouses, plus numerous antique shops and galleries. The Hudson River School of painting began in Hudson, and the homes of its two progenitors, Thomas Cole and Frederic Church, sit almost directly across the river from one another.

Where to Stay

Mount Merino Manor

Dining & Drinks

Harvest Spirits Farm Distillery

Sightseeing

Richard B. Fisher Center
Frederick Church House
Assorted paints and brushes in Thomas Cole’s studio

Day 5 : Milton

Cross the Hudson on the Rip Van Winkle Bridge and head south. Be sure to prioritize visits to the Storm King Art Center for outdoor sculpture, the United States Military Academy at West Point and a couple of wineries along the well-delineated Shawangunk Wine Trail.

Where to Stay

Buttermilk Falls Inn

Dining & Drinks

Whitecliff Vineyard Tuthilltown Spirits Henry's
Storm King Art Center sculpture -
Tuthilltown Spirits Distillery whiskey -

Day 6 : West Point & Chester

Start your morning with a tour of the United States Military Academy at West Point. From here, travel 36 miles to the southwest to Glenmere for a leisurely afternoon. 

The 18-room Gilded Age property suffered from years of neglect and decline before being spectacularly reborn with an investment of $30 million and a renovation that lasted for several years. You will be greeted by the striking sight of a Tuscan villa with pale-blue shutters set amid a classic Northeastern landscape. Formal gardens are strewn with vine-covered arbors, and a broad lawn spills down to Glenmere Lake.

95
Glenmere

Less than 50 miles from Manhattan, this elegant 18-room hilltop Italianate villa was built in 1911 as the country retreat of Robert Goelet in Chester.

United States Military Academy at West Point
United States Military Academy at West Point - Photo by Hideaway Report editor

Day 7 : Depart

Request a late checkout from Glenmere to continue taking advantage of the picturesque, extensive grounds and offerings like tennis, croquet, a heated outdoor pool and a magnificent full-service spa. Finally, make your return to Manhattan.

.itinerary-cta-bottom

Book This Itinerary

Contact a travel advisor to book your custom itinerary. Fill out the form or call (630) 734-4610.