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. Get there early and you’ll have first pick.

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.

Here’s what’s waiting for you downtown.

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.

Meet Your Favorite Nonprofits

Local nonprofit groups will have tables set up throughout the fair. Stop by, say hello, and hear what they’re working on. It’s a good excuse to learn what’s happening in town beyond the shopping.

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

Local musicians take over the fair from morning to night:

Celina Savage, followed by the New Canaan Town Band and School of Rock, at South and Elm INtersetion
New Canaan Music playing all day on Main Street

Parking Is Free

Every legal parking space downtown is free for the weekend, including the train station and commuter lots. Park anywhere legal and walk in.

Save the Date

Sidewalk Sale: Friday, July 17, 2026
Village Fair: Saturday, July 18, 2026
Elm, Main, and Forest Streets, New Canaan