On your mark, get set, GO! Sidewalk Sale season is here! We love sidewalk sales- it’s a great way to support local businesses and to score great deals! Plus many sidewalk sales are family friendly events. So save the date! Here is our guide to sidewalk sales in Fairfield County, Northern NJ, Westchester, and Long Island.
Fairfield County, CT Sidewalk Sales
Greenwich Sidewalk Sale
When: July 11-14, 2019
Where: Greenwich Avenue and surrounding streets, Greenwich CT
This popular annual event, featuring over 100 retail stores, attracts hundreds of shoppers to Greenwich Avenue and the nearby streets in downtown Greenwich to find savings and values on clothing, jewelry, accessories, gifts and more from participating retailers, restaurants and businesses. The Greenwich Sidewalk Sale is the largest outdoor sales event in all of Connecticut, encompassing four full consecutive days of bargains.
Old Greenwich Sidewalk Sale
When: June 27-29, 2019
Where: Sound Beach Avenue, Old Greenwich, CT
Stop by and browse at the annual Old Greenwich Sidewalk Sale.
The Westport Sidewalk Sale
When: June 28-30, 2019
Where: Main street, Post Road and surrounding streets in Westport, CT
The much-anticipated annual Westport Sidewalk Sale allows savvy shoppers to find amazing sales throughout Main Street, Post Road and areas surrounding downtown. Shops bring merchandise to the sidewalks and offer incredible bargains. Times will vary by store but shop early for the best selection!
Darien Sidewalk Sale and Family Fun Days
When: July 11-13, 2019
Where: Post Road and surrounding streets in Darien, CT
Stop by to score great deals at the Darien Sidewalk Sales. There will also be lots of kids activities such as face painting, balloon creations, and a treasure hunt.
New Canaan Village Fair and Sidewalk Sale
When: July 12 and July 13, 2019
Where: Main St, Elm St. and surrounding streets in New Canaan, CT
The annual fair offers local residents and regional visitors an action-packed, bargain-filled, entertaining, and delicious way to spend a summer day in one of the most charming towns in Connecticut. The event always offers many family-friendly activities, with merchants showcasing an amazing array of products and services. In recent years the Event has expanded to include a “Pre-Sale” day on Friday for New Canaan’s local merchants to put all of their merchandise out on the Sidewalk.
Fairfield Sidewalk Sale and Street Fair
When: July 20, 2019
Where: Post Road from the Heritage Square Shopping Center to the Promenade at the Brick Walk, Fairfield, CT
The Town of Fairfield and Fairfield Chamber of Commerce are pleased to co-present the Annual Sidewalk Sale & Street Fair to be held, rain or shine, in downtown Fairfield. More than fifty Fairfield businesses are expected to participate in this year’s event. Select merchants will offer advance sales of discount merchandise beginning on Thursday, July 18th. Sherman Green will feature activities for children and families, where an inflatable bounce house, face-painting, and balloon artist are all planned. This year’s event will also feature live musical entertainment at multiple venues scattered throughout the downtown. From the latest fashion apparel and jewelry to sporting goods and best-selling books, there’s something for everyone!
Wilton Street Fair and Sidewalk Sale
When: July 20, 2019
Where: Town Green at Wilton Center, 101 Old Ridgefield Road, Wilton CT
On July 20th, Old Ridgefield Road, Wilton’s main street will be closed to traffic and filled with interesting vendors, fun activities, entertainment, and delicious treats and drinks. The emphasis is on family fun for all and their dogs!
Westchester County, NY Sidewalk Sales
Rye Sidewalk Sale
When: July 25-27, 2019
Where: Purchase Street and surrounding streets in Rye, NY
Bargain hunters have a lot to choose from during Rye’s Annual Sidewalk Sale. Chamber of Commerce members throughout the city, offer discounts as high as 75%.
Larchmont Sidewalk Sale
When: July 18-20, 2019
Where: Palmer Avenue and Chatsworth Avenue, Larchmont NY
Stop by and support local businesses in the Village of Larchmont at their annual sidewalk sale.
Scarsdale Sidewalk Sale
When: July 25-27, 2019
Where: Downtown Scarsdale, NY (East Parkway, Spencer Place and surrounding streets)
Come stop by and shop the Scarsdale Sidewalk Sale! Amazing deals and plenty of shopping for all!
Bergen County, NJ Sidewalk Sales
Englewood Summer-Fest and Sidewalk Sale
When: July 25-27, 2019
Where: East Palisade Ave and a portion of West Palisade Avenue, Englewood, NJ
Downtown Englewood will be transformed into the ultimate shopping destination. Enjoy special savings! Participating stores will have racks and tables with merchandise on the sidewalk.
Ridgewood Summer Sidewalk Sale Days
When: August 1-3, 2018
Where: Ridgewood Business District, E. Ridgewood Ave and Side Streets, Ridgewood, NJ
Sizzle into Summer…Ridgewood’s Famous Summer Sidewalk Sale Days are fast approaching…do not miss this one!
Long Island, NY Sidewalk Sales
Sag Harbor Sidewalk Sale
When: October 12 – 14, 2019 (Columbus Day Weekend)
Where: Up and down main street in Sag Harbor
Local shops bring great values onto the sidewalk for you! Stroll up and down Main Street and discover all that Sag Harbor has to offer.
Mattituck Street Fair and Sidewalk Sale
When: July 6, 2019
Where: Old Sound Avenue, Mattituck, NY 11952
Their 42nd year of great tradition is coming to Mattituck! Go and enjoy an old-fashioned street fair with live music, local merchants, and the crowning of the 2019 Little Miss and Little Mister Mattituck – an event that is not to be missed!
Sayville Summerfest and Sidewalk Sale
When: August 9 – 11, 2019
Where: Downtown Sayville Main Street, Gillette Park and The Common Ground
The annual Sayville Summerfest is a fun, free, family-friendly event that draws around 5,000 attendees. Enjoy food, rides, games, music, art exhibits, vendors, a 4-mile run, a classic car show, and special savings from participating stores.
About Daisy Mae VanValkenburgh
DaisyMae VanValkenburgh is a twenty-something blogger and Instagram lifestyle influencer finishing up her BA in journalism and moving onto her MSEd in higher education administration at Hofstra University on Long Island. She is a brother of Alpha Phi Omega, an editor-in-chief for multiple companies, a social media analyst, a website builder, and a dream chaser.
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