Holiday Events

A cozy, festive hotel lobby with a Christmas tree, nutcrackers, poinsettias, vintage furniture, and a carpeted staircase.

Holiday Events

Celebrate the magic of the holiday season at Chatham Bars Inn. From festive traditions and family-friendly activities to seasonal dining, live entertainment, and creative experiences, there’s something for everyone to enjoy throughout the holiday season. Gather with loved ones and make lasting memories by the sea.

Four people stand holding large Christmas wreaths in front of a decorated Christmas tree indoors.

Holiday Wreath Decorating

Join us for another year of festive holiday decorating! Enjoy a hands-on, how-to session led by Chatham Bars Inn’s fine gardener, Pamela Vasques.

Two children with red bows are crafting at a table decorated with red and green materials and a basket of pom-poms.

Santa's Workshop

Calling all kids to Santa’s workshop at the North Pole! Once inside you will see a beautiful set up for the Winter Wonderland theme and you’ll even meet the one and only Santa Claus.

Children smiling near a decorated Christmas tree, holding teddy bears, with festive attire and holiday ambiance.

Holiday Teddy Bear Tea Party

Each child will hand-pick their very own teddy bear and bring it to life just in time for the Holidays during this special tea party with Santa’s Elves.

Arrangements of red, white, and green flowers are displayed in rustic vases on a table.

Holiday Floral Arranging

Join Chatham Bars Inn’s Fine Gardener Pam Vasques to design your very own holiday floral arrangement! Leave with new skills and your floral creation to take home with you.

A bouquet with red and white flowers, greenery, and berries, held against a blurred green background in sunlight.

Holiday Bouquet Making

Join Chatham Bars Inn’s Fine Gardener, Pamela Vasques, for an interactive Holiday Bouquet-Making Workshop, where you'll have the opportunity to design your very own floral masterpiece.

A woman in a blue dress sings with a microphone, while a man plays the keyboard, with colorful lighting.

Holiday Music Shows

An evening of live seasonal musical performances. Ticket includes one drink, holiday cookies and access to a lite bite menu.

Four people are seated around a table playing Mahjong, smiling and enjoying each other's company.

Holiday Mahjong Brunch

Shuffle, stack, and win! Join us for a lively Mahjong brunch. Enjoy great vibes, friendly competition, and a beautiful view.

A group in period attire sings by a festive fireplace, surrounded by onlookers and a decorated Christmas tree.

Carolers & Cocoa

Enjoy a complimentary hour of holiday cheer with traditional carolers, a cozy bonfire, and rich, decadent cocoa.

Christmas gifts under a tree, featuring a doll set, toy trucks, and colorful gift bags with festive decorations.

The Giving Tree

Come together in true Holiday Spirit by giving back to our local community!

A festive room filled with Christmas decorations, including teddy bears, nutcrackers, a tree, stockings, and plush animals on snowy fluff.

Teddy Bear Room

Visit the Teddy Bear Room in Room 19 of the Main Inn from November 29-December 29, where teddy bears fill the space in a festive holiday display.

A group of people enjoying drinks at a stylish bar, engaged in lively conversation, with bottles displayed on shelves behind them.

Live Music in The South Lounge

Unwind fireside in the South Lounge and enjoy live music from a rotating lineup of local performers on select evenings.

Two mugs of creamy beverage topped with spice, a red ornament, candy canes, and a fireplace in the background.

Holiday Mixology

As many of you know, our mixologists are sincerely passionate about cocktails! Join us this season for our special holiday-themed mixology classes in our Chef’s Table.

A gingerbread house setup with jars of colorful candies and sweets, holiday decorations, and a Christmas tree in the background.

Gingerbread House Workshops

Celebrate the sweetness of the season. The award-winning pastry team at Chatham Bars Inn bakes and assembles gingerbread houses and you will have the fun part - decorating them with an array of edible frosting and candy, making the experience fun, easy, and delicious.

Three people are tasting wine at a wooden table surrounded by wine racks, each holding a glass and appearing to enjoy the experience.

Holiday Wine Tastings

Join us for an immersion into the world of wine, traveling across the globe to discover the history of winemaking, oenology, and knowledge about the most famous wine regions of the world.

A festive holiday decoration with greenery, a red bow, golden bells, and painted ornaments, hangs on a vehicle.

Christmas Swag Décor Workshop at The Chatham Bars Inn Farm

Join Chatham Bars Inn’s Fine Gardener Pam Vasques for a creative, hands-on workshop celebrating Cape Cod’s coastal beauty.

A decorated Christmas tree stands in a room with white curtains, adorned with red and white ornaments, and a large bow on top.

Guest Room Holiday Decorations

Planning to stay with us at the Inn this holiday season? Make your visit extra magical by arriving to a beautifully decorated guest room, filled with festive cheer.

Forbes Travel Guide Five Star Hotel, recognized once again among the world’s finest hotels

#1 Resort in Massachusetts in the 2025 Condé Nast Traveler's Readers' Choice Awards

#1 Best Waterfront Hotel/Resort in the USA TODAY 2026 10Best Readers' Choice Travel Awards

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#1 Best Waterfront Restaurant in the USA TODAY 2025 & 2026 10Best Readers' Choice Travel Awards – Beach House Grill

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Forbes Travel Guide 2025 Hotel Icon. Recognized as one of 6 hotels in the US and 23 hotels worldwide.

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