The Red Lion Inn and Norman Rockwell Museum present: 

Black Christmas tree with silver Christmas ornament, topped with a silver star, and decorated with small white snowflakes and the words 'JOYFUL HOLIDAYS' in large white letters.
Illustration of a lion wearing a red Santa hat, a warm red scarf, and sitting on a sleigh.
SEE THE FULL SCHEDULE

All December long, The Red Lion Inn comes alive with festive pop-ups, events, and special programming to celebrate the season.

Check back often—we’ll be adding even more holiday cheer throughout the month!

SPECIAL EVENTS

A Christmas gathering outside a restaurant called The Red Lion Inn. The building is decorated with wreaths and garlands, and people are gathered on a porch singing carols. There are vintage cars parked in the foreground.

  • Join us for Courtyard concessions during Stockbridge Main Street at Christmas. Enjoy mulled wine and chili, and warm up by our cozy firepit.

    12/7: 12-2pm

BOOK YOUR STAY
A Christmas tree ornament made of small metallic jingle bells in red, green, and gold, arranged in a circular wreath, hanging from a green ribbon with a red pipe cleaner bow on top, on a Christmas tree with red lights and a blurred red ornament in the background.

  • Join Stacey and Sydney, our General Manager and Hotel Manager, for a joyful afternoon of holiday crafting! Decorate festive ornaments while enjoying rich hot cocoa — with the option to add a little extra holiday cheer for adults! — plus an assortment of cookies and brownies.

    12/3, 3PM - 4:30PM
    12/17, 3PM - 4:30PM

    Seating is limited!*

RESERVE YOUR SPOT
A display of fresh oysters on ice, accompanied by lemon wedges, in small bowls, and a bowl of dipping sauce in the center.

  • Indulge in a coastal experience with East Dennis Oyster’s exclusive pop-up on the Front Porch. Enjoy fresh, briny oysters sourced directly from Cape Cod Bay, and grab a cocktail while you take in the joyful holiday ambiance.

    12/7, 1-5PM

Person decorating a birthday cake with white icing using a piping bag, with colorful candies in the background.

  • Design your own festive gingerbread house with a variety of candies and decorations. Cookies and brownies will be available to enjoy while building your delicious creations!

    12/13, 11AM - Sold out
    12/20, 11AM - 1PM

    Seating is limited!*

RESERVE YOUR SPOT
Close-up of gingerbread cookies decorated with white icing, including a Christmas tree shape and smiley face, on white parchment paper with cookie crumbs around.

  • Get into the holiday spirit with friends and family as you create delicious cookies that will be almost too cute to eat! This event is perfect for all ages, so bring the whole crew along.

    12/10, 3PM - 4:30PM

    Seating is limited!*

RESERVE YOUR SPOT
A person dressed as Santa Claus handing out presents to children at a holiday gathering in a decorated dining room with tables, poinsettias, and holiday decorations.

  • Ho, Ho, Ho! Merry Christmas! Santa Claus is coming to town and will be at The Red Lion Inn to spread holiday cheer. Bring the kids to meet Santa, share their wish lists, and take memorable photos. Afterward, enjoy our festive brunch specials in the Main Dining Room.

    12/14, 11 AM - 2 PM

BOOK YOUR RESERVATION
SEE THE MENU
Pop art style illustration of a group of women in formal attire at a celebration, with one woman wearing a Santa hat, and another woman holding a bouquet of flowers, against a bright yellow background.

  • Join world-renowned magician Benjamin Levy for a one-of-a-kind evening of magic, mind reading, miracles, and more! In this elegant and exclusive show, you’ll witness the impossible—up close and personal. Magic will happen right in your own hands. Your thoughts will be read (only if you wish!), and you’ll experience wonders unlike anything you’ve seen before.

    12/18, 8PM

PURCHASE TICKETS
Group of nine professionally dressed individuals posing in a well-lit room with a wooden floor, American flag, and a television screen in the background.

  • Join us for a performance by the Berkshire Hills Music Academy’s Classical Ensemble, featuring five talented graduates of the Berkshire Hills music program. This accomplished group performs beautiful classical selections at community events across Western Massachusetts — now bringing their timeless sound to The Red Lion Inn.

    12/18, 1PM

Children in red uniforms singing in a church choir, directed by a conductor, with an audience watching from the gallery.

  • A talented group of children ages 6 to 13 from Berkshire County. Under the direction of Jack Brown, this chorus fosters a love of music through choral singing, featuring a diverse repertoire that includes Christmas carols, folk songs, and contemporary pieces.

    12/19, 4PM at The Red Lion Inn
    12/20, 4PM at the Stockbridge Congregational Church

People wearing Christmas socks while sitting near a decorated Christmas tree.

  • Why get dressed? Roll out of bed and join us for brunch in your coziest PJs. Sip mimosas, savor brunch favorites, and celebrate comfort in style—slippers encouraged!

    12/28, 8:30AM-10:30AM

BOOK YOUR RESERVATION
Close-up of a decorative black and white bow with a black glittery

  • Ring in the New Year with us at The Red Lion Inn, where timeless tradition meets joyful celebration! Enjoy a festive menu, an incredible magic show by world-renowned magician Benjamin Levy, live musical entertainment, a holiday photobooth to capture the moment, and a prosecco toast at midnight as we welcome 2026 together.

BOOK YOUR TICKETS

HAPPENING ALL MONTH LONG

Two people holding red enamel mugs with lemon wedges, sitting outside on a cold day. The mugs have "The Red Lion Inn" printed on them. One person is wearing a pink sweater and the other a darker sleeve.

  • Get cozy on our famous Front Porch with a cup of mulled apple cider or hot cocoa! Top off your drink with whipped cream, candy canes, or marshmallows. For an extra festive touch spike it with your choice of liquor from Berkshire Mountain Distillers!

A handwritten letter to Santa in a brown envelope, surrounded by Christmas wrapping paper rolls, candy canes, a red Santa hat, and a small striped gift box with a red ribbon, on a white wooden surface.

  • This holiday season, little ones are invited to stop by our Letters to Santa Station and share their Christmas wishes. We’ll provide festive stationery, crayons, and a special mailbox direct to the North Pole—so every child’s note reaches Santa in time for Christmas Eve. A magical tradition for families, it’s the perfect way to spark wonder and holiday cheer.

People walking through a pathway decorated with colorful celebrating Christmas lights, with trees illuminated in red, yellow, blue, and green lights, creating a festive atmosphere.

  • This season, Red Lion Inn guests receive exclusive discounted tickets to Naumkeag’s enchanting Winter Lights—a dazzling holiday experience just minutes from our door.

LEARN MORE
A large elaborate gingerbread house decorated with colorful candies, gumdrops, and icing, placed on a table in front of a framed painting with a floral wallpaper background.

  • Celebrate the holidays with a visit to our Candy House in the back dining room! This festive masterpiece is crafted from 4,952 candies and stands 62 inches long, 21.5 inches wide, and 31 inches tall, weighing around 120 pounds. It's a dazzling holiday attraction and a must-see photo opportunity! 

A cozy, decorated interior of a home during Christmas with a staircase adorned with green garland and red bows. Poinsettia plants are placed at the bottom of the stairs, and the area features a large mirror, framed artwork, Christmas-themed crockery, and a wall-mounted menorah with lit candles. A wooden table with an open book is in the foreground, and the scene is illuminated by a brass chandelier with candles and natural light from a window.

  • Gather by our majestic piano in the lobby and enjoy the performance of your favorite Holiday Songs. Feel free to sing along with them! 

A Christmas wreath made of pine branches with five pinecones attached, hanging on a wooden wall.

  • Exclusive for Red Lion Inn guests only! Join Township Four at their vintage and custom floral boutique nestled on the south side of the Inn. Get creative by crafting your holiday centerpieces or decorating a wreath to take home.

    Wreath Decorating Workshops:
    12/6, 11AM
    12/7, 2PM

    Fresh Mixed Greenery Wreath Workshops:
    12/6, 3PM
    12/13, 3PM

BOOK WREATH DECORATING
BOOK MIXED GREENERY WREATH MAKING
People walking past the Norman Rockwell Museum on a snowy day, with a white building and a sign decorated with Christmas greenery and red accents.

  • Just minutes from The Red Lion Inn, the Norman Rockwell Museum celebrates the life and legacy of America’s beloved illustrator. Home to the world’s largest collection of original Rockwell art—including his iconic Stockbridge Main Street at Christmas—the museum brings his timeless vision of community, family, and holiday tradition to life. A visit during the festive season is the perfect way to step inside Rockwell’s world and experience the magic that continues to inspire the Berkshires today.