These five 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 a Hudson Valley getaway or upstate New York!

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

Day 1: Millerton and Amenia

Village of Millerton
A hybrid of historic and eclectic, Millerton is a walkable district with the type of independent shops, cafes, and art galleries you won’t find anywhere else.  The spirit of the independent book seller is alive and well at Oblong Books and Music, established in 1975 and still the largest in the mid-Hudson Valley.

Wethersfield House and Gardens, Amenia (S)
Visit the former country estate of conservationist Chauncey Devereux Stillman, set at the highest elevation in the area to enjoy far-reaching views. The highlights include the carriage house, trails, the 1939 Georgian-style brick mansion and impressive collection of paintings, and two acres of formal gardens inspired by the Italian Renaissance, complete with resident peacocks, fountains, and a sculpture garden.

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 state-of-the-art equipment. Owned by the Four Brother's restaurant family, they’ll deliver food to your car, and even clean your windshield!

Day 2: Milan and Clinton Corners

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 views of its two lakes, 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.

Day 3: Millbrook

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 these 185 acres to a large lake surrounded by cliffs, low hills, waterfalls and streams.

Wing’s Castle, Millbrook (S)
At first glance, this stone structure looks ancient, but you’ll learn that it’s closer to 40 years old, and was built by hand by its owners using salvaged materials from antique buildings. Indoor tours are currently closed for the 2021 season but you’re welcome to walk the grounds, and check out the moat!

The Cary Institute of Ecosystem Studies, Millbrook (S)
While it’s true that this facility is an environmental research center, you’re free to explore the grounds. The campus features four leisurely hiking trails through wooded meadows and sugar maple stands. More than 126 bird species have been spotted on the lowlands landscape. Bring your picnic to Fern Glen, and enjoy the meandering boardwalk, pond, and observation deck overlooking Wappinger Creek. Open April through October.

Day 4: Poughkeepsie

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 Pastry Garden 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 sitdown meal? Try Milanese Italian Restaurant or Zeus Brewing Co. 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 5: Beacon

Mount Gulian, Beacon (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 bayonet-tipped 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.