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Discover the Best Sidewalk Sales and Festivals in and around Fairfield County This Weekend!

Fairfield County, CT, is buzzing with excitement this weekend as it hosts an array of sidewalk sales, street festivals, and arts and crafts fairs. Whether you’re a shopping enthusiast, an art lover, or just looking for a fun day out, there’s something for everyone. Here’s your guide to the must-visit events happening this weekend: 


Bethel Summer Shop & Stroll ๐ŸŽˆ๐Ÿ›๏ธ 


๐Ÿ“…Saturday, July 20th 

๐Ÿ•™ 11am-4pm 
๐Ÿ“Downtown Bethel – Greenwood Avenue, Bethel, CT
Kick off your weekend with the Bethel Summer Shop & Stroll! Enjoy great deals from local shops, delicious food from street vendors, and live music that will make you want to dance in the streets. It’s a perfect family-friendly event to start your weekend. 



Fairfield Sidewalk Sale & Street Fair ๐ŸŽˆ๐Ÿ›๏ธ 


๐Ÿ“…Saturday, July 20th 

๐Ÿ•™ 10am-4pm 
๐Ÿ“
Downtown Fairfield at Sherman Green – 1451 Post Road, Fairfield, CT
The Fairfield Sidewalk Sale & Street Fair is a beloved annual event that brings together the best of shopping, dining, and entertainment. Stroll through downtown Fairfield and discover bargains, enjoy street performances, and indulge in tasty treats from local vendors. 



New Canaan Village Fair & Sidewalk Sale ๐ŸŽˆ๐Ÿ›๏ธ ๏ธ


๐Ÿ“…Saturday, July 20th 

๐Ÿ•™ 9am-4pm 
๐Ÿ“
Downtown New Canaan – Elm, Main, and Forest Streets, New Canaan, CT
Head to New Canaan for their Village Fair & Sidewalk Sale, where the streets come alive with vibrant stalls, games, and entertainment. It’s a perfect spot to find unique items, enjoy live performances, and savor the local flavor. 



Wilton Street Fair & Sidewalk Sale ๐ŸŽˆ๐Ÿ›๏ธ

๐Ÿ“… Sat, July 20

๐Ÿ•™ Time: 10am – 3pm

๐Ÿ“ Where: Wilton Center – CT-107 & US-7, Wilton, CT

Join us for a fun-filled day with shopping, dining, music, and family activities! Enjoy live performances, "Touch-a-Truck" displays, a book sale, face-painting, and more! 


Guilford Craft Expo ๐ŸŽจ


๐Ÿ“…Friday, July 19th - Sunday, July 21st 

๐Ÿ•™ Fri, Sat. & Sun - 10am-6pm 
๐Ÿ“
Guilford Green – 33 Whitfield Street, Guilford, CT
If you love handmade arts and crafts, the Guilford Craft Expo is a must-visit. Featuring over 180 artists, this expo showcases a diverse range of crafts, from jewelry to ceramics to textiles. It’s a great place to find one-of-a-kind pieces and meet the artists behind them. 

 


Litchfield County Artisans Festival ๐ŸŽจ


๐Ÿ“…Saturday, July 20th  

๐Ÿ•™ 10am-5pm 
๐Ÿ“
New Milford Green – 10 Main St., New Milford, CT
The Litchfield County Artisans Festival brings together talented artisans from across the region. Explore a variety of handcrafted goods, from pottery to paintings, while enjoying the scenic beauty of New Milford. 



Arts Festival at Harbor Point Boardwalk ๐ŸŽจ


๐Ÿ“…Saturday, July 20 and Sunday July 21 

๐Ÿ•™ 10am-5pm 

๐Ÿ“ Harbor Point Boardwalk, 1 Harbor Point Rd, Stamford
Finish your weekend with a visit to the Arts Festival at Harbor Point Boardwalk in Stamford. Enjoy beautiful waterfront views while browsing through stalls filled with artistic creations. This festival features local artists, live music, and great food, making it a perfect Sunday outing. 


Plan Your Weekend Adventure! 

With so many exciting events happening, Fairfield County is the place to be this weekend. Grab your friends and family, and get ready to explore the best sidewalk sales, street fairs, and arts and crafts festivals.    Happy Exploring! ๐ŸŽ‰โœจ 

Discover the Best Sidewalk Sales and Festivals in and around Fairfield County This Weekend!
Live Music, Local Flavor & Family Fun: Explore Fairfield Countyโ€™s Best Events This Week!
By Cathy Ithier July 12, 2025
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