Wequassett’s Enchanted Winter

Experiences Overview

November 30, 2023–January 1, 2024

The Holidays Arrive at Pleasant Bay

Join Us for an Inaugural Winter at Wequassett

Starting with a blockbuster weekend of holiday fireworks, shopping, and sweet competition and culminating in a grand New Year’s Eve gala, it’s a season of celebrating new traditions at Cape Cod’s most celebrated resort.

Each weekend in December, we’re creating the moments so you can make the memories. From elegant high holiday teas and hot cocoa-fueled cookie-decorating parties, to Christmas shopping and cozy champagne-inflected staycations overlooking Pleasant Bay, we’re making our list and checking it twice. Food Network star Carla Hall, a trio of Broadway stars, and Mr. and Mrs. Claus themselves will be joining us to make the season bright.

We look forward to welcoming you, your families and your friends for an enchanted winter at Wequassett.

Ring in the Season

Sugar, spice and everything nice – including a Merry Market, tree-lighting and fireworks over Pleasant Bay! On Saturday, jump on the complimentary shuttle service from Lighthouse Charter School running from 2:00 to 8:00 pm, and join us at the Outer Bar starting at 3:00 pm for a delightful selection of lite bites and drinks (cash bar).

Mrs. Claus stops by for a special pajama party brunch on Sunday morning, and Food Network star Carla Hall hosts a special dinner event and plays head “chef-eree” in the inaugural Cape Cod Holiday Baking Classic to find New England’s best Christmas cookie.

A Holiday Revue & Baking, Too!

From the Great White Way to Pleasant Bay, three Broadway stars deliver a merry and bright holiday revue in Broadway on the Bay: A Cape Cod Holiday Spectacular. Mrs. Claus’s Cottage bustles with activity all weekend: Deck the halls of your very own gingerbread house, learn the art of icing (and sip a glass of champagne) from a pro, or both!

Holiday Treats for Every Taste

From an exclusive wine tasting and intimate five-course dining experience with Silver Oak Cellars on Friday night to our first Brunch with Santa on Sunday morning, it’s a weekend of culinary indulgence! Wequassett introduces Afternoon SwifTea featuring a Taylor Swift Wardrobe, polaroid photos and bracelet kits.  You’ll be Enchanted!  Surprise your sweet tooth with gingerbread house decorating and a hot cocoa bomb workshop.



Here Comes Santa Claus!

You’ve been nice all year and the big day is finally here! Gather your near and dears in the final countdown to Christmas with Afternoon SwifTea with a Taylor Swift twist, Brunch with Santa, and a little Elf Care. On Christmas Day, once the gifts have all been opened and the stockings have been emptied, join us for a festive Christmas Brunch.

Cheers to 2023!

Spend your post-Christmas weekend relaxing, reflecting and reinvigorating on the shores of Pleasant Bay, and join us in bidding adieu to 2023 with a glittering New Year’s Eve Gala and greeting 2024 with a New Year’s Day Brunch.

Overnight packages start at $1,000, inclusive of gala entry, brunch and overnight accommodations for two.

The Magic of the Season

Mrs. Claus’s Cottage offers hands-on holiday fun, from gingerbread house decorating and hot cocoa bomb classes to holiday centerpiece workshops. And in honor of Mrs. Claus and all those orchestrating holiday magic, we’ve curated a special Elf Care program to help you put yourself at the top of your holiday to-do list with spa services, complimentary gift wrapping, and holiday sweets baked by our award-winning pastry team.