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Great Barrington’s 16th annual Holiday Shop, Sip, and Stroll this Saturday

“This event brings everybody in the community together,” Chamber Executive Director Betsy Andrus told The Berkshire Edge in a past interview. “It brings out residents and out-of-town visitors together with our business owners.

Great Barrington — For the past 16 years, the Southern Berkshire Chamber of Commerce’s annual Holiday Shop, Sip, and Stroll has brought cheer to the downtown area.

This year’s event will take place throughout downtown on Saturday, December 13.

Some of the many activities and events from Great Barrington’s Holiday Shop, Sip, and Stroll over the past three years. Activities include holiday caroling, wreath-making, holiday displays in Main Street storefronts featuring local students, and a holiday hayride down Main Street. Photos by Shaw Israel Izikson.

“This event brings everybody in the community together,” Chamber Executive Director Betsy Andrus told The Berkshire Edge in a past interview. “It brings out residents and out-of-town visitors together with our business owners. It’s an inclusive atmosphere where everybody feels comfortable being here, shopping, dining, and enjoying the activities. It’s a real inclusive time for all.”

Some of the many activities and events from Great Barrington’s Holiday Shop, Sip, and Stroll over the past three years, including holiday displays in Main Street storefronts featuring local students, the lighting of a menorah at Town Hall, and a holiday parade. Photos by Shaw Israel Izikson.

This year’s event will continue the tradition of holiday cheer all throughout the downtown area.

Schedule of events

2 to 7:30 p.m.

  • Charlie’s Trains at Saint James Place, 352 Main Street

3 to 4 p.m.

  • Meet Pete the Cat at Mason Library, 231 Main Street
  • Aston Magna Family Day at Saint James Place, 352 Main Street

4 to 7 p.m.

  • Holiday photo cut-outs throughout town
  • Face painting at Lee Bank, 279 Main Street
  • Letters to Santa at Carr Hardware, 256 Main Street
  • Adult wreath-making at The Triplex Cinema, 70 Railroad Street
  • Rudolf’s Way at the Berkshire Bank entrance, 244 Main Street
  • Kids’ crafts at the First Congregational Church, 251 Main Street
  • W&T bonfire and music in the Wheeler & Taylor parking lot, 333 Main Street
  • Sweets & Scholars Market in the Pittsfield Cooperative Bank parking lot, 322 Main Street
  • Cozy Sips Supreme Cocoa Bar in the Pittsfield Cooperative Bank parking lot, 322 Main Street
  • Holiday market and bonfire in the First Congregational Church parking lot, 251 Main Street
  • Kids’ games in the First Congregational Church parking lot, 251 Main Street
  • S’mores by the fire in the First Congregational Church parking lot, 251 Main Street
  • Gingerbread house decorating at Bon Dimanche, 32 Railroad Street
  • Holiday selfie booth at William Pitt Sotheby’s International Real Estate, 306 Main Street
  • Elf Passport drop-off at Tom’s Toys, 297 Main Street
  • Kids’ balloon characters at Fluff Alpaca, 319 Main Street
  • Winter ice sculpting on the Pittsfield Cooperative Bank front lawn, 325 Main Street
  • Holiday Music by WSBS Radio throughout town
  • Mickey’s Christmas Carol Movie at The Mahaiwe’s Indigo Room, 20 Castle Street
Students from area schools taking part in the annual Holiday Shop, Sip, and Stroll in 2023. Photos by Shaw Israel Izikson.

4:30 p.m.

  • Character parade with Santa at the base of Railroad Street

4:40 to 7:30 p.m.

  • Holiday Hayride at the base of Railroad Street

4:45 to 6:45 p.m.

  • Visit with Santa in the Berkshire Bank lobby, 244 Main Street

5 to 5:30 p.m.

  • Olga Dunn Nutcracker Seedling at Saint James Place, 352 Main Street

5 to 7 p.m.

  • Berkshire Hillsmen throughout town

5:30 to 7 p.m.

  • Live window displays throughout town

7 p.m.

  • Menorah, Kinara, and Tree Lighting on the steps of Town Hall, 334 Main Street

7:15 p.m.

  • Fireworks visible throughout town

7:30 to 8:15 p.m.

  • Songs of the Season at Saint James Place, 352 Main Street

For more information about the event, visit the Southern Berkshire Chamber of Commerce’s website.

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