Summer sidewalk sales are the perfect way to catch some great deals on everything from clothing to home accessories and much more! Whether you’re looking to stock up for your next trip, grab some things for your home or even start some holiday shopping… we have a list of sales coming up in June and July, 2025. Be sure to mark your calendars and plan to get there early for the best selection! Happy shopping!
Old Greenwich
Thursday, June 19 – Sunday, June 22
The annual sidewalk sales in the Old Greenwich Business District on Sound Beach Avenue features live entertainment, giveaways, refreshments and more!
High Ridge Shopping Center, Stamford
Thursday, June 26 – Saturday, June 28
Westport
Friday, June 27 – Sunday, June 39
Merchants throughout downtown Westport participate (from Elm Street, Church Lane, Riverside Ave, Sconset Square, and Playhouse Square), and with Main Street’s sidewalks lined with sales for shoppers. Click here for a list of participating stores.
Darien
Thursday, July 10 – Saturday, July 12, 10 a.m. – 5 p.m.
Vendor locations can be found HERE. There will be 3-day pop up vendors in The Corbin District, along the Post Road, and Grove Street Plaza and one-day pop up vendors at Darien Commons on Saturday only, July 12. The Youth Entrepreneurial tent will be set up Saturday, July 12th at Bankwell.
Greenwich
Thursday, July 10 – Saturday, July 12, 9:30 a.m. – 7:00 p.m.
Sunday, July 13, 10:00 a.m. to 5:00 p.m.
Almost 100 retailers will offer their best sales during this amazing event on Greenwich Avenue and side streets off The Avenue. RAIN OR SHINE. Click here for more information.
New Canaan
Saturday, July 19, 9 a.m. – 5 p.m.
Elm, Forest and Main Streets between Burtis and East Avenue will be closed to vehicular traffic creating a “pedestrian mall.”
Wilton
Saturday, July 19, 10 a.m. – 3 p.m.
Wilton Center and Town Green will be transformed into an exciting, action packed, bargain filled, entertaining and delicious destination for residents and regional visitors. Click here for more information!
Fairfield
Saturday, July 19, 10 a.m. – 4 p.m.
More than 50 Fairfield businesses are expected to participate in this year’s event, setting up stands and offering a variety of merchandise for sale. Admission is free. Sherman Green will feature activities for children and families, including an inflatable bounce house. This year’s event will again feature live musical entertainment at several multiple venues scattered throughout the downtown.