Rolling hills and quiet landscapes; charming villages and horseback neighbors: These are just a few of the idyllic scenes that the Connecticut side of Dutchess County is known for. With award-winning restaurants, outdoor recreation, and estates aplenty, Amenia, NY should not be overlooked as a quick getaway or staycation destination. Here’s how to spend a weekend in the picturesque town.
Saturday
Start by taking in the extraordinary conservation efforts at Wethersfield Estate and Gardens, a historic house with formal gardens set on 1,000 acres. The estate is the former home of Chauncey Devereux Stillman (1907–1989), an avid conservationist, accomplished equestrian, Navy veteran, and grandson of the founder of what is now Citibank. You’ll find preserved statues and native flora in the estate’s two gardens, as well as antique paintings, furniture, and sculptures—with pieces dating as far back as the 15th century—in the Main House and Museum. Guided tours are available in warmer months; cross-country skiing is offered during winter.
Next, settle into your new digs at the Hilltop House B&B, an inviting country inn with five guest rooms decked in traditional B&B antiques and florals. Though the building itself was constructed in 1909 and the old-fashioned décor pays homage to that era, attentiveness was given to modern comforts such as luxurious new mattresses.
When dinnertime rolls around, experience Serevan’s award-winning cuisine; their menu seamlessly combines Middle East flavors with farm-fresh Hudson Valley produce. Chef and owner Serge Madikians serves up distinctive dishes like falafel-crusted snapper over ribbons of zucchini and squash.
Summer visitors can end the night with an evening flick at the Four Brothers Drive-in, where the vintage concept of a drive-in movie meets locavore menus and modern amenities: electric vehicle chargers, online food orders delivered to your car, a playground, pet area, and much more for the perfect al-fresco country evening.
Sunday
Enjoy breakfast at the Hilltop the next morning; innkeeper Sandy has received rave reviews for her hearty homestyle meals. If the inn’s old-fashioned charm has got you feeling some kind of way, downtown Amenia is home to a handful of antiques shops, including Apple Antiques and The Enchanting Cottage. Or, venture just outside of town to Millerton Antiques Center, a renowned mainstay featuring nearly 40 merchants peddling paintings, furniture, collectibles, rare books, clothing, housewares, records, and more.
After loading up on one-of-a-kind finds, zip back to town for a casual grab-and-go lunch at Back in the Kitchen or if you’re feeling leisurely, enjoy a sit-down feast at Monte’s Local Kitchen and Tap Room, where New American cuisine meets Italian flare in an inviting atmosphere.
If you arrive between May and November, make your way to Cascade Mountain Winery for an afternoon wine and cheese tasting. Vintner Bill Wetmore has been producing award-winning table wines here at the foothills of the Berkshires since 1972.
