Presented by: The Red Lion Inn and Norman Rockwell Museum

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.
2026 CALENDAR OF EVENTS

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

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

BOOK YOUR HOLIDAY STAY

‍STOCKBRIDGE MAIN STREET AT CHRISTMAS

12/06/26

Immerse yourself in the annual real life recreation of this iconic scene painted by Norman Rockwell.
Join us for courtyard concessions, sip a festive cocktail on our front porch, and enjoy an exclusive East Dennis Oyster pop-up
as you experience the magic of Stockbridge Main Street at Christmas.

front porch sips
& COURTYARD CONCESSIONS

LIVE HOLIDAY MUSIC

Enjoy the festive sounds of live holiday music in the lobby and front porch caroling throughout the season.
Stop in for a fireside cocktail and some holiday tunes, or settle in and stay for dinner – you may even want to sign along!

  • Join us throughout the holiday season for Christmas caroling on the front porch, filled with festive cheer, beloved holiday tunes, and plenty of Christmas spirit!

    12/6, 3PM - Berkshire Hills Chorus

    12/11, 7-7:30PM - Caroling with Jenni

    12/24 – 6:30-7PM - Caroling with Jenni

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

    12/5, 6-8PM
    12/12, 6-8PM
    12/19, 6-8PM
    12/23, 6-8PM
    12/30, 6-8pm

  • Please join us in the lobby for holiday harp music throughout December. Let the graceful sounds of the harp fill the season with warmth, beauty, and holiday cheer!

    12/12, 1-3PM
    12/13, 1-3PM
    12/24, 1-3PM
    12/25, 1-3PM
    12/26, 1-3PM
    12/27, 1-3PM
    12/28, 1-3PM

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.

    12/9, 3PM - 4:30PM

    Seating is limited!*

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!

    12/12, 11AM - 1PM
    12/19, 11AM - 1PM

    Seating is limited!*

  • 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.

    Fresh Mixed Greenery Wreath Workshops:
    12/5, 4PM
    12/6, 2PM
    12/12, 2PM

    LEARN MORE

    Wreath Decorating Workshops:
    12/5, 10AM
    12/12, 10AM

    LEARN MORE

  • Join us 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.

    12/16, 3PM-4:30PM
    12/17, 3PM - 4:30PM

    Seating is limited!*

CLASSES & WORKSHOPS

  • 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.

    12/13, 11AM - 3PM

*Ticketed events and workshops at The Red Lion Inn will be available for purchase November 1, 2026

  • 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!

    12/27, 8:30AM-10:30AM

FAMILY FUN at the Inn

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.

our FAMOUS CANDY HOUSE

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! 

OUR PARTNERS

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.

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.

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!