Friday Nights | 5:00PM - 8:00PM | January-March

Unlike a typical bar, this intimate setting puts the spotlight on sound. Relax, unwind, and enjoy live jazz performances from talented local and regional musicians in a cozy, candlelit atmosphere where the music truly takes center stage.

Located in the Nantucket Sound Room on the Rooftop at Pelham House Resort.

FREE Admission! No tickets required — walk-ins welcome.

Saturday, January 24th | 7:00PM - 9:00PM

Join us for an unforgettable night on the water as we honor one of the greatest bands of all time. Sing along, reminisce, and let the soundtrack of the ’60s come to life once more. Guests will be able to order food and beverages from a limited Rooftop menu. Please note that seating for this event is communal.

Saturday, February 7th | 7:00PM - 9:00PM

Comedy Night is getting a dose of classic East Coast humor with Frank Santorelli. Best known for his recurring role as “Georgie the Bartender” on The Sopranos, Frank has also appeared in films like Meet the Parents, No Reservations, and Crooked Lines. Doors open at 6:00PM. Please note this event will have communal seating. A limited Rooftop menu will be available for purchase from 6:00–8:30PM.

Saturday, February 14th | | 7:00PM - 9:00PM

Spend Valentine’s Day surrounded by the glow of candlelight and the sounds of love. The Beacon Street Quartet brings a romantic evening of classical and pop favorites to our fully candlelit Sea Level Ballroom—an intimate, one-of-a-kind musical experience you won’t forget.

Saturday, February 21st | 7:00PM - 9:00PM

Watch as two incredible pianists go head-to-head, playing your favorite tunes and taking requests on the spot. It’s all about good vibes, crowd sing-alongs, and spontaneous fun. Bring your friends, grab a drink, and enjoy an in-person experience that’s as entertaining as it is interactive! Guests will be able to order food and beverages from a limited Rooftop menu. Please note that seating for this event is communal.

Saturday, March 7th | 7:00PM - 9:00PM

Join us at Pelham House Resort for an unforgettable evening celebrating the legendary music of Johnny Cash. Gather your friends, enjoy exceptional food and drink, and sing along to the songs that shaped generations. General admission seating, doors open at 6:00 PM! The show will begin at 7:00PM. Please note: this event will have communal seating.

Saturday, March 14th | 2PM & 3PM Start Times

Cape Cod has a rich and vibrant Irish Heritage, and this is a great way to celebrate it on the Cape. Join us Saturday, March 14th to get your Irish up with the Shamrock Stoll at Pelham!

Saturday, March 21st | 7:00PM - 9:00PM

Watch as two incredible pianists go head-to-head, playing your favorite tunes and taking requests on the spot. It’s all about good vibes, crowd sing-alongs, and spontaneous fun. Bring your friends, grab a drink, and enjoy an in-person experience that’s as entertaining as it is interactive! Guests will be able to order food and beverages from a limited Rooftop menu. Please note that seating for this event is communal.

Saturday, March 28th | 7:00PM - 9:00PM

Laugh the night away at Pelham House Resort with an evening of stand-up comedy featuring three of Boston’s funniest talents — Jody Sloane, Amy Tee, and Jolanda Logan. Expect bold humor, quick wit, and plenty of laugh-out-loud moments in an intimate, high-energy setting.

Doors open early so you can settle in, grab a drink, and enjoy food from a limited rooftop menu before the show begins. Whether you’re planning a date night, a girls’ night out, or just looking for something fun to do on the Cape, this comedy night delivers. *Please note this event has communal seating*

Discover the best of Cape Cod with our curated itineraries, designed to help you make the most of your stay at Pelham House Resort. Whether you're seeking relaxation, adventure, or family fun, our personalized guides offer handpicked activities, dining, and local experiences to suit every style.