Catskills vs Berkshires: How the Two Regions Differ for a Weekend

From New York City, Woodstock and Phoenicia are about 2 to 2.5 hours away, and Hunter and Windham about 2.5. The southern Berkshires around Great Barrington are also about 2.5 hours, by the Taconic State Parkway, and Lenox is a little farther.

From Boston the order reverses: the Berkshires are about 2 to 2.5 hours west on the Mass Pike (I-90), while the Catskills are about 3.5 hours or more. The Berkshires draw visitors from both cities, while most Catskills visitors come from New York, which affects prices and who fills the inns year-round.

Since 2010, much new Catskills lodging has been design-led boutique inns and renovated motels. Inness in Accord, with 28 cabins and a farmhouse on 220 acres, and Scribner's Catskill Lodge in Hunter, a renovated 1966 lodge, are two examples. Older inns and family resorts are still common, but the boutique conversions get most of the attention.

The Berkshires have a longer history of resort lodging: the Lenox inns, many in former Gilded Age estates, came decades before the Catskills' boutique hotels. Most of the region's lodging is New England inns in Lenox and Stockbridge, wellness resorts such as Kripalu and Canyon Ranch, and inns and B&Bs in smaller towns. Fewer properties are built around design, and more are built around Tanglewood or a spa.

Many Catskills boutique inns are in the $$$ band, and Inness, Piaule Catskill and Hemlock Neversink are $$$$, with weekend prices driven by New York City demand. Berkshires inns on summer arts weekends cost about the same, but the Berkshires also have more traditional inns and B&Bs in the $ and $$ bands, especially in Lee and South County.

For travelers watching cost, the Berkshires from November to April, when the arts calendar is quiet and ski traffic is light, usually have more open rooms and lower rates. Catskills weekends stay busier through the off-season because of their closeness to the city.

The Catskills have steeper hiking, with more elevation gain and the Catskill 3500 peaks as a goal for regular visitors. Fly fishing on the Beaverkill and the upper Delaware has no real Berkshires equivalent, and Hunter, Windham and Belleayre are larger ski areas than any in the Berkshires.

Berkshires hiking is gentler: Mount Greylock and the Appalachian Trail suit a wide range of fitness levels, and the back roads suit road and gravel cycling. For downhill skiing there are Jiminy Peak and Butternut, and the rolling terrain suits cross-country skiing.

Both regions are busiest in summer and during fall foliage, with a smaller ski season in winter. In the Catskills, summer demand comes from outdoor trips and city weekends. In the Berkshires, Tanglewood, Jacob's Pillow and MASS MoCA add to it, which makes July and August harder to book than the outdoors alone would. Most of the Berkshires' summer arts season ends around Labor Day, so the weeks between Labor Day and October foliage are usually easier to book there, while in the Catskills Labor Day weekend is still a peak.