Cape Cod Resort Readies For The Holiday Season

DENNIS PORT, MA — Halloween hasn't yet happened, but spooky season makes way to holiday cheer fast, and one Cape Cod resort is already prepared.

The Pelham House Resort is ushering in the festive season with a vibrant calendar of fall and holiday events, inviting guests to gather, celebrate and make lasting memories by the sea. From lively Oktoberfest festivities and musical tribute nights to family-friendly brunches and elegant holiday dining, the resort promises something for everyone this season.

Below is a list of events at the resort:

Sunday, Oct. 26 | Oktoberfest | 12–4 p.m.

Raise a glass at the Pelham House Oktoberfest celebration featuring Devil’s Purse Brewing Co., live music by the Jonny Bass Band (12–3 p.m.), and classic Bavarian bites like jumbo pretzels and apple cider donuts. Guests can catch the Patriots game at 1 p.m. while enjoying a limited Rooftop menu. Tickets include a jumbo pretzel and souvenir beer stein filled with your Devil’s Purse beer of choice. Tickets are $35 for adults and $20 for kids. Purchase on Eventbrite.

Wednesday, Oct. 29 | Taste of Dennis | 5:30–9 p.m.

Join the Dennis Chamber of Commerce for this beloved annual tradition, featuring the area’s top restaurants and culinary talent. This year’s event is held at Pelham House Resort. Tickets available via the Dennis Chamber website.

Wednesday, Nov. 26 | Friendsgiving Dueling Pianos | 7–9 p.m. (Doors 6 p.m.)

Kick off Thanksgiving week with a high-energy dueling piano show, complete with a selection of sliders (vegetarian options available). Gather friends and toast to good times before the holiday. Tickets are $45 + tax on Eventbrite.

Thursday, Nov. 27 | Thanksgiving Day Buffet & To-Go Dinners | 11:30 a.m.–5 p.m.

Celebrate Thanksgiving with an indulgent buffet on The Rooftop or enjoy the flavors of the day at home with To-Go Turkey Dinner Kits. A special welcome hour begins at 10:30 a.m., with the last seating at 5 p.m. Reservations required on OpenTable. To-Go kits available on Eventbrite (order by 11/13). More details and menus available at on Pelham Resort’s website.

Saturday, Nov. 29 | Johnny Cash Tribute Show | 7–9 p.m. (Doors 6 p.m.)

Enjoy an unforgettable evening featuring a tribute to Johnny Cash’s greatest hits. The Rooftop’s limited menu and a full cash bar will be available. Tickets are $35 on Eventbrite.

Saturday, Dec. 13 | Winter Market | 11 a.m.–4 p.m.

The Pelham House Winter Market returns for another year of holiday cheer. Browse a curated selection of local vendors, enjoy festive bites, and sip seasonal cocktails at the cash bar. Free admission.

Sunday, Dec. 14 & Sunday, Dec. 21 | Brunch with Santa

Make holiday memories with Brunch with Santa on The Rooftop, featuring photo opportunities and festive fare.

Reservations required on OpenTable.

Saturday, Dec. 20 | Kris Kringle Crawl | Start Times: 2 p.m. or 3 p.m.

Get into the holiday spirit with the Kris Kringle Crawl, a lively three-stop bar crawl across the property featuring themed cocktails, snacks, and live entertainment. Tickets are $40 on Eventbrite.

Monday, Dec. 22 | Holiday Family Dueling Pianos | 6–8 p.m. (Doors 5 p.m.)

A family-friendly twist on the fan-favorite dueling pianos show—filled with laughter, singalongs, and holiday spirit. Tickets are $35 on Eventbrite.

Wednesday, Dec. 24 | Christmas Eve Dinner | 4–7 p.m.

Celebrate Christmas Eve with a warm and elegant dinner on The Rooftop, offering stunning views and seasonal flavors.

Reservations required on OpenTable.

Saturday, Dec. 27 | Frank Sinatra Tribute Show | 7–9 p.m. (Doors 6 p.m.)

Experience the timeless charm of Frank Sinatra in this special live tribute performance. Tickets are $35 on Eventbrite.

Wednesday, Dec. 31 | New Year’s Eve Dinner on The Rooftop | 5–10 p.m.

Ring in 2026 with live music, dinner, a champagne toast, and coastal views during a festive evening of fine dining. Reservations required on OpenTable.

Thursday, Jan. 1 | New Year’s Day Brunch & Dinner

Welcome 2026 with brunch (10 a.m.–3 p.m.) and dinner (4–8 p.m.) service on The Rooftop—the perfect way to start the new year with family and friends. Reservations required on OpenTable.