1. TIVOLI | Poets and Scholars
The center of Tivoli, a hamlet in the town of Red Hook, is tiny, starting around the Lost Sock Launderette and ending a block later at Murray’s (murraystivoli.com), an airy cafe set in a 19th-century brick church where you can imagine the lanky patrons in metallic-washed boots are talking about Kierkegaard—Bard College is 3 miles away. In the middle of the stretch, artists Brice and Helen Marden’s 11-room Hotel Tivoli (hoteltivoli.org) stands sentinel, a colorfully appointed affair whose farm-to-table restaurant, the Corner, is the beating heart of the hamlet. The overall draw of Tivoli? Poetic beauty. Scenic trails run through Tivoli Bays, a freshwater wetland, and a 10-minute drive south, Poets’ Walk meanders through the former estates of the Astor and Delano families. Bard’s Frank Gehry-designed performance center warrants a stop, followed by a stroll through the 1903 Italianate Blithewood Garden, also on the campus.
2. BEACON | Art Buffs
The 2003 opening of Dia: Beacon—with its 240,000-square-foot gallery space devoted to contemporary art—was a game changer for America’s former “Hat Making Capital.” The revival continues, evident in the percolation of carefully considered shops and galleries along Main Street. Browse the cool clothes at Kaight (kaightshop.com), fine wood pieces at Wickham Solid Wood Furniture (wickham.com), the works of a dozen contemporary artists at the Beacon Artists Union (baugallery.com) and the mega-textural and equine paintings at Terreson: Beacon (jterreson.com).
3. HUDSON | Nesters
Jennifer and Kim Arenskjold of Arenskjold Antiques (arenskjold.com) were pioneers on Warren Street, the nexus of the antique and vintage furniture trade that made Hudson a bull’s-eye for interior designers. Word spread. Begin shopping steps from the train station with the Riverfront Antiques and Design Center (hudsonradc.com), a mix of old shutters and farmhouse tables, and work your way up Warren Street to high-end dealers like Regan & Smith (reganandsmith.com), Finch (finchhudson.com), Richard Kazarian and Neven + Neven Moderne (nevenmoderne.com). Les Indiennes Outlet is an Indian-fabric-lover paradise (lesindiennes.com) and Hawkins NY (hawkinsnewyork.com) offers a trove of home goods, linen sheets, blown glass vases and pink marble serving boards among them.
4. KINGSTON | Hipsters
The telltale signs are all there: restored Victorian homes next to less fortunate clapboard brethren, bars like the Stockade Tavern (stockadetavern.com) specializing in bespoke cocktails, and an influx of trendy shops. The first capital of New York, Kingston was torched by the Brits who proclaimed it “a nest of rebels” in 1777. The independent spirit and a bit of grittiness persist in the historic Stockade District where Lovefield Vintage, a pristine clothing shop on Front Street (lovefieldvintage.com) sits next to Bluecashew Kitchen Homestead (bluecashewkitchen.com) and its luxe-modern cooking and service pieces. O Positive, a nonprofit that organizes health care for artists in exchange for their work, started in Kingston, which explains the elaborate building murals.
5. COLD SPRING | Hikers
On weekends you’ll see troops of urban escapees marching from the Metro North train station, water bottles dangling from daypacks, to the Hudson Highlands State Park trailheads just outside this village. The easy-level Little Stony Point trail quickly ascends to a dramatic view of the Hudson and, down the road, the Cornish trail leads to the crumbling remains of a once-grand estate. One of the area’s most popular day hikes, Breakneck Ridge, is just north and as the name suggests, not for the novice—or for procrastinators; it’s closing for a year or so of maintenance on January 1. Fuel up with shirred eggs at Hudson Hil’s Cafe on Main Street (hudsonhils.com).
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