From Poughkeepsie: 1 hour, 15 mins
The pastoral Litchfield Hills area, with its quaint, rustic vibe, is most notable for what it doesn’t offer — a snooty, Hamptons-like, look-who’s-here scene. What it does have is laid-back, preppy charm aplenty, making it a perfect destination for a fall weekend jaunt to commune with nature, rediscover your significant other, and catch a bit of culture.
Connecticut Wine Trail
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Destinations are spread out, providing an excuse to take some rambling leaf-peeping drives through countryside dotted with picturesque stone walls, horses grazing behind classic white-rail fences, historic churches, and tiny blink-and-they’re-gone villages. Take advantage of opportunities to get outdoors and hike, bike, and kayak. Or chase a little white ball around gently rolling hills at the aptly named Fairview Farm Golf Course, which offers quintessential Litchfield County vistas of red barns among the challenging holes.
Infinity Music Hall & Bistro
If romance is on the menu, explore the nearby CT Wine Trail with its charming vineyards and four-season tasting rooms, then enjoy intimate, candlelit fine-dining at the Old Inn on the Green. Artsy types will appreciate the Connecticut Art Trail, with its art studios, world-class museums, and historic sites (the $25 Art Passport gives you access to 18 local museums). And don’t miss a concert at Infinity Music Hall & Bistro in Norfolk, a cool performing-arts venue in a renovated 1883 opera house with an on-site bistro (reserve tickets in the mezzanine if you want to eat dinner during a performance).
STAY: Rock Hall Luxe Lodging
Hidden behind tall wrought-iron gates and up a long curving drive, this estate on 23 private acres in Colebrook, CT, is the perfect spot to delight in a quiet weekend with a special someone. The grand manor house — the only extant Addison Mizner home north of the Mason-Dixon line — positively oozes sophisticated romance with its wood-burning fireplaces, four-poster beds, and deep soaking tubs. (You can also schedule a relaxing couples massage in your elegant “sleeping chamber.”) A welcome variety of activities are available on-site, including a marked forest-hiking trail, tennis, apple picking in its own orchard, bicycling, and door-to-door carriage rides through the countryside. Indoor enticements include a billiards room, Scrabble nook, a vintage pinball machine, and a screening room with complimentary boxes of Raisinets.
From $325/night; www.19rockhallroad.com