The $500 Weekend Resort-Town Smackdown!

Photograph by Jason Houston

GREAT BARRINGTON, MA

Getting There (and Back)
Car, $40 (gas); two hours each way

Where to Stay
Driving yourself leaves enough cash to splurge a bit on accommodations. Slumber in style at the homey Wainwright Inn (starting at $100 a night), with its four-poster beds and gorgeously preserved 18th-century structure.

Where to Play
The Berkshires are a farm-to-table fiend’s playground. Sample raw-milk cheese at Cricket Creek Farm in Williamstown, witness maple syrup in the making at Hancock’s Ioka Valley Farm, and knock back fine wines and hard apple cider at Furnace Brook Winery in Richmond (12-wine tasting: $10).

One Great Meal
In Lenox, Wheatleigh’s four-course tasting ($125) of impeccably sourced haute cuisine—local veal, New Zealand prawns, Burgundy snails—may well be the highlight of your trip, if not the sum of your culinary experience. Dress accordingly.

Two Worthy Hangouts
Brunch belongs to Rubi’s, a hip haunt for sipping bubbly ($6), eating gooey halloumi cheese toast ($7), and ogling weekending Manhattanites. At Castle Street Café, the hot cider spiked with locally made Berkshire Mountain Distillers rum ($9) is an unsung gem.

Bottom Line
$397 + $40 (gas supplement for wayward gastro-touring) = $437

Photograph by Getty Images

NEWPORT, RI
Getting There (and Back)
Bus, $50 (Peter Pan); 90 minutes each way

Where to Stay
With ocean views, a sprawling indoor pool, elegant gambrel-style architecture, and prime white-sand real estate, Newport Beach Hotel and Suites ($89 a night) is a discerning penny-pincher’s dream.

Where to Play
Nothing like a heaping helping of voyeurism into the lives of the Gilded Age’s filthy rich to make frugality feel noble. The Breakers, the Vanderbilts’ 70-room summer home, is the must-see manse, but the $28 “winter passport” gets you into the Elms and Marble House, too.

One Great Meal
The terrific locavore cuisine at Castle Hill Inn and Resort comes with a side of matchless scenery. Three courses plus one glass of wine: $89.

Two Worthy Hangouts
Brick Alley Pub attracts locals and, well, tourists like us for stiff martinis ($9), and it easily rates the short list for lunch. Hit 22 Bowen’s for a Germain-Robin XO cognac ($24) whichever evening you’re still sporting post–Castle Hill finery.

Bottom Line
$378

Photograph by Todd Bissonette

SARANAC LAKE, NY

Getting There (and Back)
Plane, $199 (Cape Air); 90 minutes each way

Where to Stay
Perched graciously along Upper Saranac, the Point is lodging at its most luxe. But with half the budget already blown on airfare, four-digit suites are out, and $68 (a night) rooms at clean, cozy, close-to-it-all Hotel Saranac are in.

Where to Play
This picturesque hamlet has long inspired painters (Winslow Homer), composers (Béla Bartók), and writers (Robert Louis Stevenson, whose summer cottage is now a museum; $5). Spot—and sponsor—modern-day masters at the Adirondack Artists’ Guild gallery.

One Great Meal
Deli by day, wine café by night, the Brown Dog in Lake Placid serves inventive contemporary-American fare. Five courses plus wine pairings: $89.

Two Worthy Hangouts
Bunking at a posh ski resort—or skiing, for that matter—is beyond this trip’s budget. But for the price of an Irish coffee ($10), you can après-ski like a trust-funder at Lake Placid’s swanky High Peaks lobby bar. Waterhole presents live music nightly, often free of charge.

Bottom Line
$439 + $50 (two roundtrip taxi fares into Lake Placid) = $489

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