This Idyllic New England Village Made Famous by Norman Rockwell Offers the Perfect Winter Escape

A vintage car driving down the Main Street of Stockbridge, MA.
Photography by Stockbridge Chamber of Commerce, Joel Laino

Text by Cindy Cooper

Many speak of Stockbridge, Massachusetts, as the perfect town, filled with quaint shops, friendly people, and vintage cars just as its most notable resident, artist Norman Rockwell, depicted in his distinctive paintings.

A vintage blue truck parked in front of a Main Street store in Stockbridge, MA.
Photography by Stockbridge Chamber of Commerce, Joel Laino

This year during the holidays, visitors can go back in time at the 32nd-annual Main Street at Christmas Recreation, during which the town transforms into a scene from one of Rockwell’s paintings. Residents of the area affectionately hold on to this holiday celebration and reenactment, with this year’s events focused on holiday music. As the events draw near, the town’s chamber of commerce will provide any updates to the schedule of seasonal celebrations.

A group gathered around a Christmas tree singing carols.
Photography by Stockbridge Chamber of Commerce, Joel Laino

Nearby, the Berkshires offer many outdoor experiences, such as cross-country skiing or snowshoeing, in towns like Charlemont or Lenox, encouraging exhilarating adventures along the snowy trails. The countryside offers back roads for cycling, hiking, and bird-watching as you explore all Western Massachusetts has to share with visitors to the state.

An exterior image of the Red Lion Inn in Stockbridge, MA.
Photography by Stockbridge Chamber of Commerce, Joel Laino

WHAT TO DO IN STOCKBRIDGE, MA

SHOPPING

7 Arts Gift Shop; 413-298-5344

Williams & Sons Country Store; stockbridgecountrystore.com

DINING

Michael’s Restaurant of Stockbridge; michaelsofstockbridge.com

Once Upon a Table; onceuponatablebistro.com

LODGING

The Inn at Stockbridge; stockbridgeinn.com

The Red Lion Inn; redlioninn.com

GARDENS

Berkshire Botanical Garden; berkshirebotanical.org

Naumkeag House & Gardens; thetrustees.org/place/naumkeag

THEATRES, MUSEUMS & GALLERIES

Norman Rockwell Museum; nrm.org

Chesterwood; chesterwood.org

Schantz Galleries Contemporary Art; schantzgalleries.com

Berkshire Theatre Group; berkshiretheatregroup.org

For more information, visit stockbridgechamber.org.

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