A Massachusetts organization is giving away cash every day during May, and you can win multiple times.

Kiwanis of Southern Berkshires (formerly Sheffield Kiwanis) is selling cash calendars. Each calendar is $10.00 and the organization is selling only 1,000 calendars.

There will be a winner every day in May 2026, and calendar holders are eligible to win every day. That's right, as I mentioned earlier, you can win more than once. Each day's prize is noted on the calendar.

Some daily prizes are $50, other daily prizes are $100 and $200. The biggest prize is on Memorial Day, which is $500.

You can purchase calendars here as well as at a bunch of local businesses in and around southern Berkshire County, including the following:

Sheffield

  • Bachetti's Auto Sales
  • Berkshire Styles
  • Gulotta's Mobile
  • Silk's Variety
  • Watson Automotive

Great Barrington

  • Agway
  • Dempsey's Auto
  • Larkin LTD
  • Seward's Tire

Canaan, CT

  • Canaan Auto Parts
  • Cranes Outdoor Power Equipment

West Stockbridge

  • Floor Store
  • Town Hall

Just a reminder that you do not have to be a Berkshire County resident to purchase cash calendars and to support Kiwanis of Southern Berkshire. You can live anywhere...Boston, Springfield, Worcester, even another state... anywhere.

Kiwanis of Southern Berkshire is selling these cash calendars to continue their mission, which is supporting the local youth in our community.

Chartered in 1954, Kiwanis of Southern Berkshire proudly serves the towns of Alford, Egremont, Great Barrington, Monterey, Mount Washington, New Marlborough, Sheffield, Stockbridge, and West Stockbridge.

If you are interested in becoming a Kiwanis member or just want to learn more about Kiwanis, you can do so by going here.

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