Guide to Sidewalk Sales in Fairfield County, Northern NJ, Westchester and Long Island

Guide to Sidewalk Sales in Fairfield County, Bergen County and Westchester County

On your mark, get set, GO! Sidewalk Sale season is here! 

These New York suburbs sidewalk sales are serious events with amazing deals to be had. 

You can score great buys at unbelievable outlet-like prices.

Greenwich Sidewalk Sale

I suggest you save the date and make sure you clear your calendar and book a sitter. 

Oh, and parking can get crazy and difficult, either carpool, take an Uber or go first thing in the morning before the crowd arrives.

Below I’ve compiled the sidewalk sales happening around the New York suburbs of Westchester County, Fairfield County and Bergen County! 

Greenwich Sidewalk Sale

Happy Shopping New York Suburbs!

Connecticut Sidewalk Sales (Fairfield County)

Greenwich Sidewalk Sale

When: July 13, 2023 to July 16, 2023

Where: Greenwich Avenue and Surrounding streets, Greenwich CT

Time: 10 am to 6 pm, at the retail store’s discretion

The Greenwich Sidewalk Sales event is the shopping event of the year with four full consecutive days of bargains!

Greenwich Sidewalk Sale

This popular annual event, featuring over 110 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.

Check out our guide to Greenwich Sidewalk Sale

Old Greenwich Sidewalk Sale

When: June 22, 2023 to June 25, 2023

Where: Sound Beach Avenue, Old Greenwich, CT

Come enjoy the annual  Old Greenwich Sidewalk Sale and check out the great summer bargains.  

Old Greenwich Sidewalk Sale

The Westport Sidewalk Sale

When: June 23, 2023 to June 25, 2023

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. 

Vineyard Vines Sidewalk Sale

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 

When: July 13, 2023 to July 15, 2023

Where: Post Road and surrounding streets in Darien, CT

Time: 10 am to 5 pm, rain or shine.

Stop by at the Darien Sidewalk Sales to score great summer shopping deals this 2023! 

JCrew Sidewalk Sale

The will also be lots of kids activities at the Darien Sidewalk Sales such as face painting, balloon creations, a treasure hunt and more for all ages to enjoy.

New Canaan Village Fair and Sidewalk Sale

When: July 21, 2023 to July 22, 2023

Where: Main St, Elm St., and surrounding streets in New Canaan, CT

Time: Friday: 10 am to 4 pm and Saturday: 9 am to 4 pm

The annual New Canaan Village Fair and Sidewalk Sale offer 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. 

New Canaan Sidewalk Sale

The event always offers many family-friendly activities, with merchants showcasing an amazing array of products and services. 

Check out our guide to New Canaan Sidewalk Sale

Fairfield Sidewalk Sale and Street Fair

When: July 15, 2023, 10 am to 4 pm

Where: Post Road from the Heritage Square Shopping Center to the Promenade at the Brick Walk, Fairfield, CT

The Annual Fairfield Sidewalk Sale will be held on July 15, rain or shine, in downtown Fairfield. 

Sidewalk Sale

More than 75 Fairfield stores and businesses are expected to participate in this year’s event. 

Select merchants will offer advance sales of discount merchandise beginning on Thursday, July 13th. 

Sherman Green will feature activities for children and families. There will be an inflatable bounce house!

This year’s Fairfield Sidewalk Sale 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 at Fairfield Sidewalk Sale!  

Wilton Street Fair and Sidewalk Sale

When: July 22, 2023

Where: Old Ridgefield Road, Wilton CT

Opens from 10 am to 3 pm, rain or shine

The Wilton Chamber of Commerce will host its 11th annual Wilton Street Fair and Sidewalk Sales from 10 am to 3 pm. 

Sidewalk Sale

Stop by at Wilton Street Fair and Sidewalk Sale for shopping, food, entertainment with music, live performances, and many new activities for the whole family (and furry friends too)!

Ridgefield Summer Fest 2023

When: July 29, 2023

Where: Town Hall 400 Main Street, Ridgefield, CT 06877

Time: Saturday:10 pm to 2 pm

Come to Ridgefield Summer Fest! Ridgefield’s Summer Fest is more than a sidewalk sale- it is a fun-filled day with lots of shopping, music, circus and even a Touch a Truck! 

JCrew Sidewalk Sale

Shop the sidewalk sale and score great deals in downtown Ridgefield.

There will also be family friendly activities such as a circus, music and art in the park as well as a Touch a Truck at Lounsbury House.

Main Street will be closed to traffic from Prospect Street to Governor Street (Bailey Avenue is closed to traffic too) to host Kids Zone, Farm Stands, Music and over 50 Vendors.

Don’t miss Ridgefield’s Summer Fest and Sidewalk sale!

New York Sidewalk Sales (Westchester County)

Rye Sidewalk Sale

When: July 20, 2023 to July 22, 2023

Where: Purchase Street and surrounding streets in Rye, NY

Come to Rye’s Annual Sidewalk Sale from July 20 to July 22, 2023.

Sidewalk Sale

Score discounts of up to 75% at the Rye Sidewalk Sale. The 3 day Rye Sidewalk Sale promises to be the shopping event for bargain hunters! 

Rye Ridge Plaza Sidewalk Sale

When: June 22, 2023 to June 24, 2023

Where: Rye Ridge Plaza at 142 South Ridge Street, Rye Brook, NY

The annual Rye Ridge Plaza sidewalk sale is back! 

The Rye Ridge Plaza sidewalk sale starts on Thursday, June 22 and ends on Saturday, June 24, 2023. 

Shoppers can find incredible bargains at the annual Rye Ridge Plaza sidewalk sale!

Greenwich Sidewalk Sale

Larchmont Sidewalk Sale

When: June 1, 2023 to June 3, 2023

Where: Palmer Avenue and Chatsworth Avenue, Larchmont NY

The Larchmont Sidewalk Sale is hosting its biggest sale of the year this 2023!

Stop by at Larchmont Sidewalk Sale for live bands, al fresco dining, cotton candy, lemonade, pretzels, and unbelievable deals!

Let’s support local businesses in the Village of Larchmont at their annual sidewalk sale and get Up to 90% off at your favorite shops!

Chappaqua Summer Sidewalk Sale 

When: July 27 to July 29, 2023

Where: King Street, Chappaqua NY

More than 20 Chappaqua merchants will be participating in this year’s Chappaqua Summer Sidewalk Sale. 

From jewelry and handbags to apparel and art, the Chappaqua Sidewalk Sale is a perfect opportunity for both residents and visitors to buy quality merchandise at incredible prices!  

There will also be food sampling, family-friendly activities and a DJ at this year’s Chappaqua Sidewalk Sale! 

sidewalk sale

Scarsdale Sidewalk Sale

When: July 27 – 29, 2023

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! 

This year, the Scarsdale Sidewalk Sale will start on Thursday, July 27th through Saturday, July 29th in Scarsdale Village, from 10am-6pm, rain or shine.

New Jersey Sidewalk Sale (Bergen County)

Englewood Summer-Fest and Sidewalk Sale

When: July 28, 2023 to July 29, 2023 from 11 am to 5 pm

Where: East Palisade Ave and a portion of West Palisade Avenue, Englewood, NJ

Englewood Sizzling Summer Sidewalk Sale Days is back!

Downtown Englewood will be transformed into the ultimate shopping destination.

Enjoy special savings at this year’s Englewood Sidewalk Sale! 

Sidewalk Sale

Participating stores will have racks and tables with merchandise on the sidewalk. 

Come shop Englewood’s Sidewalk sale for incredible bargains!

Ridgewood Sidewalk Sale

When: October 5-7, 2023

Where: Downtown Ridgewood and West Side, Downtown Ridgewood and the West side

Time: 10 am to 6 pm

The  Ridgewood Sidewalk Sale starts on Thursday, October 5, 2023 and ends on Saturday, October 7, 2023.

Get ready to shop at Ridgewood Sidewalk Sale!

Don’t miss the great deals and fun shopping experience!

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