WELCOME TO THE

HOLIDAY SEASON

SEE THE FULL SCHEDULE

Celebrate the magic of the holidays in the heart of the Berkshires at The Red Lion Inn. From our twinkling Main Street porch to festive dining in our historic tavern, every corner of the Inn shines with New England charm. Enjoy seasonal menus, cozy fireside gatherings, and timeless holiday traditions that have delighted guests for generations. Stroll through Stockbridge’s iconic downtown—made famous by Norman Rockwell’s Stockbridge Main Street at Christmas—and experience the warmth, wonder, and nostalgia of the season.

HAPPENINGS & HELPFUL INFORMATION:

People gathered outside a red building decorated with holiday garlands, watching a holiday choir performance. The building has a second story with decorated potted Christmas trees and flags on a balcony.

ALL DECEMBER LONG: JOYFUL HOLIDAY EVENTS

Elegant dining room decorated for Christmas with white tablecloths, wooden chairs, and Christmas garlands with red bows, featuring a chandelier and windows with curtains.

DINING

A live music performance in a dimly lit venue with band members playing instruments and a singer, surrounded by an audience sitting at tables with drinks.

LION’S DEN

A backyard with a swimming pool, outdoor furniture, and a wooden fence. In the background, there is a large white house with multiple chimneys and leafless trees, and snow on the ground.

POOL & HOT TUB

Pop art style image of a Christmas scene.

BENJAMIN LEVY’S EXCLUSIVE CHRISTMAS SHOWS

Two people walking through a tunnel decorated with colorful Christmas lights, with lights forming trees on each side and a dark sky visible at the exit.

NAUMKEAG’S WINTERLIGHTS

Decorated Christmas tree with lights, pig and cow ornaments, plush pig and cow toys, and handwritten notes, set indoors with wooden walls and signage nearby.

FESTIVAL OF TREES

The cast of a theatrical performance dressed in period costumes standing on stage with a dark cityscape background.

A CHRISTMAS CAROL

Indoor craft market with tables displaying jars, plants, and holiday decorations. Shoppers browse various handmade items in a brightly lit space.

BERKSHIRE BOTANICAL GARDEN’S HOLIDAY MARKET

Decorated room with red poinsettias, Christmas gift boxes, garland with red berries, poin!as, and red bows on the staircase, vintage wallpaper, grandfather clock, large mirror, and a round wooden table with a decorative bowl, illuminated by a hanging lantern.

FAMILY DAY AT CHESTERWOOD

A small town street decorated for Christmas with wreaths and garlands, a clock with a red bow, and a row of brick buildings including a hotel, a creamery, and shops.

HOLIDAY SIP & STROLL

A dark wooden wall with a wooden cross in the center, surrounded by lush green plants, including a pine branch with pinecones, large leafy plants, and tropical foliage.

TOWNSHIP FOUR CLASSES

Person pouring tea from a blue and white teapot into a cup on a pink floral saucer with a spoon on the table.

AFTERNOON TEA

Decorative shop entrance with Christmas trees, poinsettias, and holiday decor. Blue door with glass panes, floral carpet, and vintage dishes and teapots displayed above.

THE SHOP AROUND THE CORNER

People skiing on a snowy slope near a ski lift with snow-covered trees in the background.

THE BERKSHIRES

A gray tabby cat with a collar lying on a colorful rug in front of a decorated Christmas tree with ornaments and decorations.

MOMENTS