Ten Places on Cape Cod to Test Your Trivia & Have a Tipple This Winter

Head out to a Cape Cod pub for a mug of frosty beer and some trivia or karaoke.

Yes, it is winter on the Cape once again, and as dreary as January and February can be, there are beacons that shine in the cold, dark night. While some places may shutter up early, others are lively scenes.

A plus to going out during the winter on Cape Cod? Way fewer people. This means that not only will you be able to have fun, but there will be far less of a commotion. You might even be able to socialize! Here are some great places to wet your whistle and have a good time on Cape Cod.

  1. Trivia Night with Patrick at Oliver's & Planck's Tavern, Yarmouth Port: Every Wednesday night starting at 7pm, visitors to Oliver's can come and test their knowledge for fun and prizes. This is a great way to get out on a Wednesday night!

    Another fun thing at Oliver's? Most Fridays, starting at 9:30pm, it’s karaoke with Mike Rock. Belt out your favorite hits and have a good time!
  2. Bar Pong, Trivia, and more at Tommy Doyle's, Hyannis: Whether you are into dancing, playing games, or showing up strangers with your trivia knowledge, Tommy Doyle's has the event for you. Check here to see their various event listings.
  3. Trivia, Karaoke, and other fun at Seaside Pub, Hyannis: Again, there is something for everyone at the Seaside Pub in Hyannis. On Thursday nights, test the limits of your brain with “drink while you think” team trivia starting at 8pm. Tuesday and Wednesday nights feature karaoke starting at 9pm. On Friday, DJ A.D.D. is in the house, taking requests and livening up the bar. Check here for a full listing of events.
  4. Bingo at the Atlantic House (Little Bar), Provincetown: For those on the tip of Cape Cod (or maybe those who don’t mind venturing up for an evening), bingo in the Little Bar at the A-House – hosted by Tiki Bronstein – is quite the experience. Bring a sense of humor and get ready to have a spectacular Wednesday night (bingo starts at 9pm according to the website). Bronstein is an alias for Scott Townsend who is better known as Thirsty Burlington. Confused? Then head up here to figure it out! The A-House is also open year-round for dancing, so come and live it up.
  5. Open Mic and Karaoke nights, the Claddagh Inn, Harwich: Whether you are an aspiring singer (Monday night is Open Mic night) or just a fan of not hitting the high notes (Wednesday night is Karaoke night), the Claddagh is a nice, laid-back bar located right on Route 28 in Harwich. Come and have a beer and either enjoy some new talent or clear the bar out with your rendition of "Don’t Stop Believin'".
  6. Trivia Night, All American Bar and Grill, Dennis: Every Monday night is Trivia Night at the All American Bar and Grill, right on Route 134 in Dennis. Starting at 8pm, test your knowledge in a variety of subjects and have a marvelous evening with old friends or new acquaintances.
  7. Karaoke and Trivia Nights, Liam Maguire’s, Falmouth: Again, a variety of fun nights for all sorts of personalities. Karaoke starts a 9pm on Tuesday nights, while Trivia begins at 8pm on Wednesday nights. For a full schedule of events, click here.
  8. Trivia at the Chatham Squire, Chatham: On Thursday night, from 7pm-9pm, come and see how far your mental faculties stretch at Trivia Night at the Chatham Squire. This Chatham staple has other entertainment as well. Click here for a full listing.
  9. Trivia Night, Wharf Pub, Edgartown: If you find yourself on Martha’s Vineyard during the winter, don’t despair. The fun doesn’t end on Cape Cod! The Wharf Pub in Edgartown has a very popular trivia night every Wednesday (be there at 7:30pm).
  10. Events Galore, the Rose and Crown Pub, Nantucket: The island of Nantucket doesn’t have much going on in the dead of winter, but the Rose and Crown Pub does its best to keep spirited events around throughout the year. The Rose and Crown reopens at the end of January. Click here for a full list of events for February, including a poker night and karaoke.

So get out and have a good time, don’t mind the time of year! There’s something fun on the Cape and Islands for everyone, no matter what the season. All that’s needed is a readiness to have a fabulous time.

About the Author

Contributing Writer

Mati Brown holds a Journalism degree from the University of Massachusetts – Amherst. She has written for several publications, including the Berlin Reporter, EDGE publications, and the Falmouth and Mashpee Bulletins. A current resident of Brewster, she is glad to be writing about the area she grew up in.