Evening Entertainment

Cape Cod is full of evening entertainment! Whether you’re in the mood for a movie, a sporting event, or a good concert, this is the place for you. Here is a list of some of our favorite ways to spend the evening.

Band Concerts

Every Friday evening from July until the end of August, a band concert is held in Kate Gould Park on Main Street in Chatham. It is truly a magical event and one that should not be missed.


The Veterans Field in Chatham is the home park of the Chatham Anglers, one of the ten teams that make up the Cape Cod Baseball League. The league is partially funded by major league baseball and features premier college players. The times for the games are posted at the Chatham Rotary and run from mid-June thru mid-August.


Chatham is proud of its small town movie theater, the Orpheum, with two screens featuring current movies, documentaries, and special viewings for the changing seasons and events.  The adjoining cafe branch of Vers serves up fantastic food, wine, and beer – which they will pack to enjoy in the theater. This is not your typical Lowes!

For a more traditional theater, visit the ten-screen Entertainment Cinemas in Dennis and get comfortable in stadium seating.  The theater is about 20 minutes from the inn; our staff is delighted to print the schedule and directions if you wish.

One of the few remaining drive-in theaters in the country is just 30 minutes from the Captain’s House Inn and is a popular destination for summer travelers.  The Wellfleet Drive-in features double header films in season; the adjacent snack bar is perfect for a casual bite while enjoying the flicks.


The Squire, in downtown Chatham, offers live entertainment on weekends. 28 Atlantic at the Wequassett Inn, just ten minutes from the Captain’s House Inn, hosts a jazz festival on Tuesday and Wednesday evenings in summer. Mahoney’s in Orleans, 15 minutes from our inn, offers Thursday evening jazz entertainment. Joe’s Beach Bar & Grille, also in Orleans, hosts weekend musicians. In Harwich Port, 20 minutes away, Mooncussers Tavern has a variety of live music on weekends in season. For lite bites, a varied wine list, and live entertainment, check out the Harvest Gallery Wine Bar on route 6A in Dennis (a 25 minute drive). Local music events can also be found by checking local newspapers or websites for listings.


  • Chatham Orpheum Theater
  • Monomoy Theatre
  • Chatham Drama Guild
  • Academy of Performing Arts
  • Cape Cod Melody Tent
  • Cape Rep Theatre

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