
Mark your calendar for New Canaan’s biggest weekend of the summer ! Friday the 17th kicks things off with the sidewalk sale. Local stores set up right outside their doors with once-a-year deals on some of their best inventory. And then, Saturday the 18th is the main event — three streets turned into a pedestrian mall packed with bargains, food, live music, and enough kids’ activities to wear out even the most energetic five-year-old.
- Shop the Sale
Storefronts up and down Elm, Main, and Forest put out their best deals of the year for the sidewalk sale. Bring a bag and budget more time than you think you’ll need — this isn’t a quick stop.
- The YMCA Family Fun Area
Head to Main and Elm for the YMCA’s Family Fun Area, the go-to spot for kids all weekend. On deck: bungee jumping, airbrush tattoos, a family photo booth, arts and crafts, and prizes.
- More Entertainment for Kids (and Adults Who Act Like Kids)
Fan favorite Gary Sirico returns with his balloon animals — a fair tradition that always draws a crowd. A face painter will be on hand for anyone who wants a new look for the day, and a psychic will be reading for anyone curious what’s next.
- Eat and Drink Your Way Through Town
Food is everywhere this weekend, but here’s where to find some of the highlights:
Taco Tequila Truck — Elm and Park
New Canaan Butcher — Main and East
Gelatissimo, Good Day Tap Company, and LemonNates — cool refreshments to beat the July heat
- Music All Day, All Over Downtown







Walter Stewart’s and Stewart’s Wine & Spirits are proud sponsors of the annual 








