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The Ashland Chamber of Commerce is making it easy to choose shopping small this Christmas Season.

November 18, 2023- January 19, 2024

The Ashland Chamber of Commerce is offering 3 Drawings of $250.00 in Chamber Dollars for shopping small!

The Ashland Chamber and Downtown Merchants want to emphasize the importance of shopping small and shopping local all year round. This Christmas season we invite you to think of the small retail businesses in Ashland first, before shopping online and hitting the send button!  There are a variety of unique, locally owned retail businesses that offer personalized services and products.  Did you know Ashland has more than 31 locally owned retail businesses?

Want to win $250 by shopping in a small locally owned retail business in Ashland?   It’s easy:

  • Starting November 18, Shop at locally owned small retail business, in Ashland and keep your receipts. 1st drawing deadline is Wednesday, December 6, 2023, at 4pm – drawing Friday, December 8, 2023.  2nd deadline Wednesday, December 20, 2023 – drawing Friday, December 22, 2023, 3rd deadline Friday, January 19, 2024–drawing Monday, January 22, 2024.
  • Staple all of your receipts, or copies of receipts, to an entry form
  • Maximum receipts of $1,000 or 100 tickets per entry.
  • Forms and your receipts can be remitted by dropping them off at the Ashland Chamber office, Moores on Main, or mailing them to P O Box 746, Ashland, WI or emailing them to


For every $10 you spend downtown between November 18, 2023 and January 19, 2024, you will receive one entry.  Double points for any receipts  November 24 (Black Friday), November 25 (Small Business Saturday) and December 2 (Customer Appreciation Day)

  • The first deadline will be Wednesday, December 6 at 4pm drawing will be Friday, December 8, 2023.  (The Chamber will do the math) Winner Robert Houle!
  • The 2nd deadline will be Wednesday, December 20 drawing will be held on December 22, 2023   (The Chamber will do the math)  Winner Briana Sterken!
  • The 3rd deadline will be Friday, January 19, 2024 drawing will be held on Monday, January 22, 2024 (The Chamber will do the math)  Winner Dianna Trush!


Frequently Asked Questions :

  • Q) Do I need to submit a separate entry form every time I spend $10? A) No. Save your receipts for each drawing time frame and then staple them all to one entry form. We’ll do the math for you and give you one entry for every $10.  November 24 (Black Friday), November 25 (Small Business Saturday) and December 2 (Customer Appreciation Day)
  • Q) I submitted my receipts, but now I spent another $10. Can I get another entry? A) Yes! You can submit your receipts as many times as you would like over the course of the entry period, but be sure to read the answer to the next question for more details!
  • Q) Will you add all of my receipts together? A) If you submit all your receipts on one entry form, then the answer is yes. $30 spent at numerous locations would give you a total of 3 entries. However, if you submit numerous entry forms over the entry period, the math will be done for whatever receipts are attached to each form. Remember, you receive double points for any receipts on November 24 (Black Friday), November 25 (Small Business Saturday) and December 2 (Customer Appreciation Day). All receipts will stay in for all 3 drawings so you can keep adding on receipts.  For example, if you spent $30.00 on Small Business Saturday, you get 6 chances.  Your chances stay in the drawing for all three drawings.
  • Q) Can I send copies of my receipts? A) Yes
  • Q) Where is the entry form?  A) Click here for a pdf.
  • Q) How old must you be to participant?  A) Must be 18 or older to participate.

Thank you for Shopping Local; and Shopping on Main….Before You Shop Online!!!

Shop Small Win Big Entry Form

For more information contact our office at 715-682-2500.