Contests

We know you count on us to have the best contests with the biggest prizes. That's why we are giving you a chance to win up to $5,000 starting Sept. 12. Here's everything you need to know.

Think you’re a football expert? Make your picks here for every regular season pro football game this year.

WIN CASH 
Fall 2019 - RULES 
Sweepstakes Name: “Win Cash”
Station(s) :WUPE FM
Station Address:211 Jason Street.
Station City, State, Zip Code: Pittsfield, MA 01201
Station Telephone: (413) 458-1001
Townsquare Media, Inc...

Want to be a winner too? keep listening!

No matter the reason, we all can agree that now is the best time of the year to have some extra bills in your wallet. That's why we're giving you THREE chances to win up to $5,000 weekdays through May 31.

Your chance to win $5,000 from us is coming May 16. Where will you be listening when you win? We have the perfect suggestions for where in the city you should settle in while listening for your chance to win.

Listen all this week for the "Prince Music Montage" for your chance to win tickets to the Purple Xperience!

Your favorite radio station has your back. We're giving you three chances to win $5,000 and we want you to have everything you need to know to win.

Win Cash Officials Rules

Before the winning starts on March 28, we wanted to give you a few reasons why you need an extra $5,000.