Lenox in May

Summer rules Lenox, specifically July through August when Tanglewood's season runs full swing. The Boston Symphony Orchestra, guest artists, and special events pack the calendar, but also pack the town with visitors. Hotel rates hit their peak, restaurants fill up, and you'll need to book everything well in advance. But the energy is electric, and those warm evenings listening to music under the stars are pretty magical. Fall brings different rewards - September and October offer spectacular foliage, cooler hiking weather, and significantly fewer crowds. Many cultural venues scale back, but you'll find better deals and easier reservations. Spring starts slowly in the Berkshires, but June offers a sweet spot with mild weather, blooming gardens, and the start of Tanglewood's season. Winter transforms Lenox into a quieter retreat. Some restaurants close, but the spas stay busy, and there's something appealing about cozy fireside evenings after a day exploring snow-covered trails. Just know that many outdoor attractions shut down completely.