The Hudson Valley has four distinct seasons and each brings its own appeal. Spring (April–May) sees the orchards blossom and the trails dry out — a good time to hike before the summer crowds arrive. Summer is busy, especially weekends, when New York City day-trippers fill the restaurants and climbing crowds pack the Gunks. Expect warm, humid days and cool nights.
Autumn is arguably the best time to visit. The Shawangunk Ridge and surrounding hills put on an extraordinary foliage display from mid-October through early November — the "leaf peeping" that draws visitors from across the region is genuinely worth the hype here. The air is crisp, the trails are uncrowded midweek, and the light on the ridge is extraordinary.
Winter is quiet. Most restaurants and shops stay open, the skiing at Mohonk is available in good snow years, and ice climbing becomes an option on the frozen seeps of the Gunks. If you come in winter, you'll largely have the place to yourself.
The New Paltz Regatta (summer), local art fairs, and seasonal events at the Huguenot Street historic site add interest throughout the year.