Wequassett’s Enchanted Winter
Experiences Overview
November 29, 2024–January 1, 2025
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(508) 432-5400
The Holidays Are Back on Pleasant Bay
Join Us for Winter at Wequassett
November 29 & 30
Ring in the Season with Music
The season kicks off on November 29th with Broadway on the Bay returning! From Broadway to Pleasant Bay, join John Riddle (Phantom of the Opera, Frozen) and Alysha Umphress (On The Town, American Idiot) for an intimate evening of music and other surprises as they romp through the nostalgia of the holiday season. Spanning the musical stylings of Dolly Parton, Cher, and Frosty (the Snowman), you’ll be cozier than a chestnut roasting on an open fire.
December 7
Merry Market, Tree Light & Fireworks
Whether your holiday shopping is just starting or well underway, find the perfect gift for everyone on your list at our Merry Market, featuring local shops and a few surprises from our holiday partners. Join us for our grand Tree Lighting and watch Santa’s magic illuminate Wequassett. After the ceremony, sit back, relax, and be dazzled by a breathtaking display of Fireworks lighting up the night sky! Be cheerful, laugh, and indulge in some delicious treats on this very special evening.
December 8
Cape Cod Holiday Baking Classic
Gather your sprinkles, sift that flour, and preheat your ovens for the second annual Cape Cod Holiday Baking Classic on Sunday, December 8th ! Get ready for an experience that’s anything but cookie-cutter! Tickets are available to taste the sweet treats, enjoy the judges’ commentary, and have fun!
In addition, children’s complimentary cookie decorating will be on the Garden Terrace from noon to 1pm and Thoreau’s will be serving lunch from 11:30am to 2pm.
December 6, 7, 13, 20
Gingerbread House Parties
Dive headfirst into a whirlwind of frosting, sprinkles, and pure imagination. Imagine a land where gumdrops are trees, licorice are fences, and windows are made of sparkling sugar crystals. Join our gingerbread house parties and challenge your creativity, spend time with the family, and sip on some hot cocoa. Festive cocktails will also be served as well as a buffet for the little ones.
December 8, 15, 22
Pajama Brunch
Join us in your pajamas for a cozy breakfast with classic dishes and sweet treats. Breakfast is available 7:00-11AM and a special holiday guest will be doing the rounds 8:00-10:00AM.
$45 per adult and $20 for ages 3 to 12
Thursday, December 19th
Chunky Blanket Class
This holiday season, step into the charm of Claus Cottage and join us for a hands-on crafting experience, guided by our talented friends from South Shore Blanket Co.. You’ll learn how to create your very own ‘Chunky Blanket’—and the best part? No knitting needles required, just the magic of your fabulous hands!
This class is perfect for newbies and experts alike—so bring your friends, get creative, and enjoy some laughs!
Cheers to 2025!
Spend your post-Christmas weekend relaxing, reflecting and reinvigorating on the shores of Pleasant Bay, and join us in bidding adieu to 2024 with a glittering New Year’s Eve Gala and greeting 2025 with a New Year’s Day Brunch.
Overnight packages start at $1,000, inclusive of gala entry, brunch and overnight accommodations for two.
