Berkshires in December

October owns the spotlight, but it's not the only show. Peak foliage typically hits the first two weeks of October, when maples explode in reds and oranges along Route 7. Hotels jack up rates and require 2-3 night minimums. Book accommodations by August if you want October weekend availability. Summer brings Tanglewood season from late June through Labor Day. Boston Symphony Orchestra performs Friday and Saturday evenings, with lawn seats starting around $25. The weather is perfect – warm days, cool nights, minimal humidity. June and September offer the best value. You'll find lower hotel rates, fewer crowds, and pleasant weather for hiking. Spring comes late to the Berkshires, with May still feeling tentative. But by Memorial Day, everything is green and hiking trails have dried out. Winter transforms the region into a different place entirely. Ski areas like Jiminy Peak and Berkshire East operate, but many restaurants and attractions close or reduce hours. The trade-off: you'll have places like the Clark Art Institute nearly to yourself.