These three days will bring you to the smaller towns and villages throughout Dutchess County, to give you a taste of rural living, independent business spirit, and offbeat adventures you won’t easily find elsewhere in the Hudson Valley or upstate New York!

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

Day 1: Milan, Clinton Corners, Amenia

Wilcox Memorial Park, Milan
This tucked away, 615-acre county park was formerly the estate of Mrs. Frederick P. Wilcox, and its 18th century complex of farm buildings still stand today. Bring a picnic and enjoy the lake views, or rent a boat and go fishing! Birdwatchers will spot the resident heron as well as many other species. There are also more than five miles of hiking trails, with a scenic overlook of Stissing Mountain and the Catskills.

Clinton Vineyards, Clinton Corners
The European tradition of exclusively growing and bottling an “estate” wine was introduced in this rural pocket of Dutchess County in 1976. Specializing in award-winning Seyval Blanc and sparkling Seyval Naturel, Clinton also produces handcrafted fruit and dessert wines. Visit the historic barn where the wine is made, enjoy a sample in the tasting room, and explore the landscape of gardens and vines.

Movie at the Amenia Drive-in (S)
When was the last time you watched a movie outdoors, from your car? Settle in for a drive-in movie in Amenia at a great location complete with new state-of-theart equipment. Owned by the Four Brothers restaurant family, they’ll deliver food to your car, and even clean your windshield!


Day 2: Millbrook and Poughkeepsie

Innisfree Garden, Millbrook (S)
You’ll find one of the “world’s best gardens,” here in central Dutchess County. Largely the work of landscape architect Lester Collins, its design is influenced by a Chinese style dating back 1,000 years, but it remains a distinctly American stroll garden. Explore the paths connecting these185 acres to a large lake surrounded by cliffs, low hills, waterfalls and streams.

Frances Lehman Loeb Art Center, Poughkeepsie
Cézanne, Matisse, O’Keeffe, Picasso, and Pollock. Works by these masters are tucked away in this manageablysized museum on the Vassar College campus. Even better, they’re free to see! The collection of more than 18,000 works are curated around themes and time periods, beginning with Middle Eastern and Asian antiquities, progressing through the Hudson River School painters and the 21st century.

Get your Italian Food Fix in Poughkeepsie
Known locally as the Mount Carmel district, the neighborhood that sits under the Walkway Over the Hudson along Verrazano Boulevard, Mill Street, and Mt. Carmel Place is where to get the best Italian pastries around. Let your sweet tooth lead you to Caffè Aurora, or La Deliziosa Italian Pastry Shoppe. Italian immigrants, who arrived here in the late 1800s, built this neighborhood as well as the Walkway, then known as the Poughkeepsie Railroad Bridge, and brought their culture and their flavors to Dutchess County. Voted Best Sandwich and Best Deli by Hudson Valley Magazine readers year after year, Rosticceria Rossi & Sons, on South Clover Street, is known for its authenticity and freshly made deli meats and cheeses. Looking for a sit-down meal? Try Milanese Italian Restaurant or Amici’s, both on lower Main Street.

Locust Grove, Poughkeepsie
Originally the home of artist and Morse Code inventor Samuel F. B. Morse, this 200-acre estate includes an Italianate villa designed in 1851 by architect Alexander Jackson Davis. Today you can tour the museum and walk through the formal gardens and nature preserve. Art and antiques fans will love the collections amassed by subsequent owner Annette Innis Young displayed in the 25-room mansion.

Day 3: Fishkill and Beacon

Mount Gulian, Fishkill (S)
To learn what a soldier’s life was like during the Revolutionary War, come to this circa-1730 colonial homestead. The Verplanck family turned it over to the Continental Army during the War for Independence, because of its strategic riverside location. General Fredrich Von Steuben—“Drillmaster of the Continental Army”—trained local farmers to fight with bayonettipped muskets.

Bannerman Castle Tour from Beacon (S)
From Beacon’s ferry dock, you can board the boat that transports you to this tiny island in the middle of the Hudson River. Native Americans thought it was haunted, but that didn’t stop Frank Bannerman from building a castle as a warehouse for his military surplus business. Bannerman Castle Trust now offers tours of the island, where you can enjoy 360° river views while supporting its efforts to preserve the building.

Town Crier Café, Beacon
First opened in 1972, this celebrated performance space for live American roots, jazz and world music recently re-opened in the middle of buzz-worthy Beacon. You’ll still be able to catch big-name artists, but now you also can enjoy a farm-to-table menu made from organic ingredients.