The event runs along Corbin Drive and the Post Road.
There will also be a young entrepreneur tent at Bankwell, where teen entrepreneurs will be selling homemade items, including jewelry and baked goods.
The event will feature shopping, a My Balloon Guy, face painting and free ice cream tickets that can be redeemed at Gofer Ice Cream.
"This is different from a lot of other communities that might have chain stores. There are no chain stores here. We live here, I live here, they live here. So you get all these locals, you're really dealing with our neighbors and that's something really important," says Bill Jensen, chairman of the Darien Chamber of Commerce.
The sale runs Friday and Saturday from 10 a.m. to 5 p.m.