Holiday Shop, Sip & Stroll


December 14, 2019 @ 3:00 pm – 8:30 pm
Downtown Great Barrington

The annual Holiday Shop, Sip and Stroll will take place in downtown Great Barrington on Saturday, December 14!

Read the full list of activities here

Join the Southern Berkshire Chamber of Commerce (SBCC) and this year’s “Event Sponsor” Lee Bank for this great community event. This year’s Holiday Shop, Sip & Stroll will be held on Saturday, December 14th in Downtown Great Barrington, MA.

Store to Store Holiday Hospitality runs all day.

All Stroll activities are FREE and begin with “An Hour of Magic” from 3-4pm at the Mason Library, where you can pick up your “Elf Passport,” get stamps at the Stroll Activities and enter to win!

From 4pm – 7pm Stroll Activities include Kid’s Crafts at the First Congregational Church Parish Hall, Holiday Market and Fire Pit at the First Congregational Church parking lot, “Face Painting” at Lee Bank, “Letters to Santa” at Fuel Coffee Shop, “Kids Games” in front of Wheeler & Taylor, “S’mores by the fire Pit” at Berkshire Community College, “Charlie’s Holiday Model Railroad” at Saint James Place, “Holiday Photo Booth” at William Pitt Sotheby’s, “Holiday Photo Cutouts” up & down Railroad Street, “Holiday Hayride” loads & unloads on Railroad Street, “Adult Wreath Making” in the Barrington House Lobby, “Live Windows” throughout town, and “Gingerbread House Making” at 286 Main Street (the former Baba Louie’s location).

At 4:30pm, “Santa’s Character Parade” begins at the base of Railroad Street, and “Visits with Santa” begin upon Santa’s arrival to the Berkshire Bank Lobby until 6:45pm.

Follow the Steiner Carolers through Town to the “Menorah & Tree lighting” beginning around 7:00pm at the GB Town Hall and fireworks are at 7:10pm and can be seen throughout town.

Our finale is a performance by the Berkshire Children’s Chorus at 7:45pm at Saint James Place.

The SBCC strives for this community event to be accessible and free to all. This could not be achieved without our generous sponsors. Thank you to: Lee Bank, The Mason Library, Seward’s Tires, CHP, First Congregational Church, William Pitt Sotheby’s, Kwik Print, Pittsfield Coop Bank, Wheeler & Taylor, Berkshire Community College, Saint James Church, Greylock Federal Credit Union, North Plain Farms, Taft Farms, Iredale Cosmetics, Salisbury Bank, Kiwanis of Sheffield, Verizon Wireless Zone, The Berkshire Children’s Chorus, WSBS Radio, and the Shopper’s Guide.