Although most towns host some comparable event, Chatham’s free band concerts—40 players strong—are arguably the best on the Cape and attract crowds in the thousands. This is small-town America at its most nostalgic, as the band, made up mostly of local folks, plays those standards of yesteryear that never go out of style. Held in Kate Gould Park (off Chatham Bars Ave., in the center of town) from July to early September, it kicks off at 8pm every Friday. Better come early to claim your square of lawn (it’s already a checkerboard of blankets by late afternoon), and be prepared to sing—or dance—along. Call tel. 508/945-5199 for information.
Summer theater is alive and well on the Lower Cape, with well-respected theater troupes in each of the three main towns. About 2 1/2 miles east of Brewster center, the Cape Cod Repertory Theatre (3299 Rte. 6A; or; tel. 866/811-4111 or 508/896-1888), mounts performances Tuesday to Saturday nights at 7 or 8pm, as well as a Sunday 2pm matinee, from early July to early September. Tickets are around $35. This shoestring troupe tackles the Bard, as well as serious contemporary fare, at an indoor theater as well as an outdoor theater on the old Crosby estate (now state-owned and undergoing restoration). On Tuesday and Thursday mornings at 10am they also offer plays for kids.
Chatham’s entry is the Monomoy Theatre (776 Route 28; tel. 508/945-1589), a small historic theater where a company combining college students and professional actors steals the show with eight productions a summer, mid-June to August. The schedule usually offers a well-balanced mix of comedies, classics, musicals, and a Shakespeare play or two. Not only do they perform Tuesday through Saturday at 8pm, they also have a 2pm matinee on Thursday. Tickets are $25 to $30. 
Over in Orleans, The Academy Playhouse, 120 Main St. (tel. 508/255-1963), makes a fine platform for local talent in the form of musicals and drama, recitals, and poetry readings. The 162-seat arena-style stage is housed in the town’s old town hall (built in 1873). Tickets are $24 to $28. July through August, there are generally shows Tuesday to Sunday at 8pm, as well as a children’s theater series ($10 per ticket) on Friday and Saturday mornings. The Academy Playhouse hosts performances year-round; check the website for a schedule. 
Bars & Live Music
Hot local bands take the tiny stage seasonally at the Woodshed, at the Brewster Inn & Chowder House, 1993 Route 6A (tel. 508/896-7771), a far cry from the glitzy discos on the southern shore. If your tastes run more to Raitt and Buffett than techno, you’ll feel right at home in this dark, friendly dive. Cover charge $5.
In Orleans, BNI (tel. 508/255-0212) is a big old barn of a bar that might as well be town hall: It’s where you’ll find all the locals exchanging juicy gossip and jokes. Live music ranges from jazz to rock to blues. There’s never a cover. There’s also often live music at Land Ho!, the best pub in Orleans. Performers are on the bill on Monday and Tuesday nights in season, and Thursday and Saturday off-season. There’s usually no cover.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.