December 13th | 11:00AM-4:00 PM

Celebrate the season with us at Pelham House Resort’s Winter Market, featuring 20+ local vendors, festive shopping, food for purchase, a cash bar, and plenty of holiday cheer.

*The application for vendors has closed. Please reach out for any questions: kelsey@pelhamhouseresort.com 

December 14th & December 21st | 10:00 AM-1:00 PM

Join us on the Rooftop for Brunch with Santa, a festive morning of great food, holiday cheer, and a chance to meet the big guy himself.

December 20th | 2:00PM & 3:00PM start times

What’s better than a Christmas bar crawl? Join us for the “Kris Kringle Crawl” at Pelham House Resort! On Saturday, December 20th we’ll kick off a festive stroll beginning at 2:00 PM and again at 3:00 PM, with holiday-themed cocktails, snacks, and live music at multiple stops throughout the resort. Grab your friends, dress in your favorite winter-festive attire, and enjoy a merry afternoon of spirited fun and seasonal surprises.

December 22nd | 6:00PM - 8:00PM

Two of the top entertainers on the East Coast play all your favorite holiday songs—come sing along, drink along, and dance along! Doors open at 5PM for a welcome hour with food available for purchase from our limited Rooftop menu.  Please note that seating for this event is communal.

December 24th | 4:00PM - 7:00PM Reservations Available

Spend Christmas Eve on the Rooftop with us, enjoying holiday specials, ocean views, and a warm, festive atmosphere. We’ll be serving our regular dinner menu alongside a selection of special holiday additions crafted by our culinary team.

December 27th | 7:00PM - 9:00PM

Join us for a night of music from internationally acclaimed Frank Sinatra tribute artist and singer, Patrick Tobin! Doors open at 6PM for a welcome hour before the show, with a limited Rooftop menu available to order from throughout the evening. Please note that seating for this event is communal.

Ring in the New Year with our Rooftop Dinner, served from 5–10pm with festive specials, live music, and a champagne toast.

Start the year off right with our New Year’s Day Rooftop Brunch, served from 10am–3pm with delicious food and sweeping ocean views.

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.

January 3rd | 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.

January 10th | 7:00PM - 9:00PM

Get ready to relive the magic of Sir Elton! Soak up the hits, the sparkle, and the piano-driven nostalgia at our Elton John Tribute Night.

Guests will be able to order food and beverages from a limited Rooftop menu. Please note that seating for this event is communal.

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.

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.

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.

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.

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.