The main street of Lenox  features many high-class boutiques and art galleries to occupy the rich during their idle time. One of the least pretentious is the Wit Gallery (27 Church St., 413/637-8808, www.thewitgallery.com ), which features whimsical sculptures and surrealistic paintings that pop from the frames.
Meanwhile, one of the most unabashedly fun is The Gifted Child (72 Church St., 413/637-1191, 10 a.m.–6 p.m. Mon.–Sat.; closed Sun.), a mishmash of games and books for toddlers, kids, preteens, and teens, plus cooler-than-cool clothing for all of the above ages.
In nearby Lee, Prime Outlets (50 Water St., Rte. 20, Lee, 413/243-8186, www.primeoutlets.com , 10 a.m.–9 p.m. Mon.–Sat.; 10 a.m.–7 p.m. Sun.) features discounted clothing and housewares from dozens of name brands, including Bass, Coach, and Liz Claiborne.