Nighttime entertainment can be tough to come by in these quiet parts, but there’s usually a good crowd at Wolfe’s Tavern (90 N. Main St., 603/569-3016, www.wolfeboroinn.com , breakfast, lunch, and dinner) at the Wolfeboro Inn. The authentic New England–style pub (with several fireplaces and pewter beer mugs strewn across the ceiling) serves food, but later in the evening, it’s all about the beer—more than seventy kinds. If you drink all 70 (no more than 2 a visit, alas), you’ll get to kiss the moose head and hang your own mug on the ceiling.
The active community of Wolfeboro  is home to dozens of events throughout the year. The Great Waters Music Festival (80 Academy Dr., 603/569-7710, www.greatwaters.org , July–Sept.) draws top performers from nearly every genre, including classical, jazz (Branford Marsalis, Dave Brubeck), folk (Judy Collins, Natalie MacMaster), and Broadway (Linda Eder).
Aerodynamic and not-so-aerodynamic crafts alike race in the Vintage Race Boat Regatta (603/569-4554, www.nhbm.org , Sept.), which takes place alternating years under the auspices of the local boat museum.