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Top Things to Do in and around Fairfield County this week Aug 17 – Aug 23, 2025: Music, Hot Air Balloon Festival, Carnivals & more!

Summer is in full swing across Fairfield County, offering everything from live music to fairs and family fun. This week (Aug 17–23), highlights include John Oates with The Good Road Band at Westport’s Levitt Pavilion Friday, and Josh Ritter’s storytelling songs on Wednesday. Aquila’s Nest Vineyards hosts a Janis Joplin tribute, while Woodbury Brewing rocks with Led Zeppelin classics. Families can enjoy the Chester Fair, Norwalk’s “Treesure Hunt,” and the Plainville Hot Air Balloon Festival.


This week’s Featured Sponsor: Edmond Town Hall, Newtown

Edmond Town Hall kicks off its Fall Concert Series with two incredible nights of live music you won’t want to miss!  


🎤 Taylorville Band – A Tribute to Taylor Swift 

📅 Thursday, August 21 | 7:00-9:00pm 


Send your kids back to school on a high note with an energy-packed evening of Taylor Swift’s greatest hits. Dress in your favorite Tay Tay outfit and get ready to sing and dance in the aisles! 

👉 Fairfield After Dark subscribers get $10 OFF each ticket with code SAVE10. 

🎟️ Grab your tickets here 


🎸 The Lightfoot Band 

📅 Thursday, August 29 | Labor Day Weekend Kickoff 


This is not a tribute act—these are the original musicians who toured and recorded with Gordon Lightfoot for decades. Featuring Rick Haynes, Barry Keane, Mike Heffernan, Carter Lancaster, and Andy Mauck, the band delivers Gordon’s music with unmatched authenticity. 


On the 50th anniversary of the Edmund Fitzgerald tragedy, their performance of the iconic ballad takes on special meaning. Fans can expect classics like If You Could Read My Mind, Sundown, Early Morning Rain, plus rare deep cuts—and even meet the musicians after the show. 

🎟️ Grab your tickets here 


Thank you to Edmond Town Hall for bringing world-class concerts, shows and community events to Newtown this season!

See ETH’s full Fall Line here. 


Browse the full calendar to plan your next summer outing. 


Summer Concerts, Festivals and Fun Things to Do  

Sunday Aug 17 – Saturday, Aug 23, 2025  


Sunday, Aug 17  


Monday, Aug 18  


Tuesday, Aug 19  


Wednesday, Aug 20 


Thursday, Aug 21  


Friday, Aug 22  


Saturday, Aug 23  

Top Things to Do in and around Fairfield County this week Aug 17 – Aug 23, 2025: Music, Hot Air Balloon Festival, Carnivals & more!
August 17, 2025
The Palace Theatre is proud to announce its upcoming Charity Golf Outing, taking place on Monday, September 22nd, 2025, at Shorehaven Golf Club in Norwalk, CT . Golfers of all skill levels are invited to enjoy a fun-filled day of golf including BMW of Darien’s hole-in-one contest, a silent auction, and charitable giving. The outing features a shamble format, ensuring a dynamic and engaging round of golf for all participants. Registration includes flexible options—from individual players and foursomes to sponsorship packages. Golfing packages include snacks and beverages on the course, plus a cocktail hour and a catered lunch and dinner. Michael Moran , President & CEO of the Stamford Center for the Arts, encourages everyone to join in and make a meaningful impact: "Swing into action for a cause that drives change. Join us for a round that makes a difference!" Event Details: • Date: September 22nd, 2025 • Time: Tee Time at 11:30 a.m. • Location: Shorehaven Golf Club, 14 Canfield Avenue, Norwalk, CT • Entry Fees range from $450 per golfer / $1,900 per foursome; sponsorship opportunities are available for those wishing to support the arts while gaining visibility and aligning their business with a prominent, mission driven organization. You can register or learn more here , or contact Laurel Lea, Director of Philanthropy, at (203) 517-3416 or mailto: LLea@palacestamford.org. Join us in making a positive impact through golf! About The Palace Stamford The Palace Theatre is the longest-running arts presenter in Fairfield County. Part of Stamford Center for the Arts (SCA), a nonprofit 501(c)(3) organization, The Palace is dedicated to serving as the region’s premier performing arts center, providing exciting entertainment that enhances and enriches the cultural, educational, economic, and social life of our community.
August 17, 2025
Dust off your lederhosen and dirndls! Westoberfest returns Saturday, October 4, in downtown Westport! Celebrate fall at the 8th Annual Westoberfest Craft Beer & Family Fall Festival, a vibrant downtown celebration featuring local craft breweries, live music, family-friendly activities, food trucks, market vendors, competitions, and more. Beer Tasting Tent (21+): Grab your 2025 commemorative glass and enjoy unlimited tastings from local and regional breweries from 1 to 5 p.m. Festival Admission: Includes access to all festival activities, including live music, kids' activities, food, vendors, competitions, and more. Tickets on sale now at westportdowntown.com/westoberfest. Buy early and save as prices increase at the door!
By Annette Einhorn August 14, 2025
Stamford Downtown is proud to announce the completion of the Sidewalk Art in Stamford Downtown Placemaking Project—an initiative aimed at enhancing the pedestrian experience through vibrant, interactive public art. The project features five permanent sidewalk murals by local artist Chancellor Hayes, known on Instagram as @8ballcreates , now on view at key locations throughout Stamford Downtown. From playful prompts to whimsical visuals, each piece invites passersby to engage with the city in a joyful, unexpected way. The installations include: "Smile Here" at Kiwanis Park (Atlantic Street) "What Will You Read Today?" at the entrance to the Ferguson Library (Broad Street) "Jump" and "Kiss Here" in Columbus Park near the flagpole and on Washington Blvd. "Playground Club" in Latham Park Hayes, whose signature style fuses vibrant color with playful direction, approached this project with energy, imagination, and deep care—transforming ordinary sidewalks into unexpected moments of joy. “Public art is a powerful tool for placemaking,” said Michael Moore, President of Stamford Downtown. “These sidewalk installations not only brighten our public spaces but also invite people to interact with their surroundings in creative and uplifting ways. Chancellor’s work brings a sense of wonder and personality to Stamford Downtown, and we’re proud to have partnered with him on this meaningful project.” Cheryl Vukelic, Stamford Downtown’s project manager for the initiative with Chancellor, shared, "It has been a pleasure collaborating with a young artist such as Chance on such a fun and meaningful project." The Sidewalk Art Project is a permanent placemaking initiative by Stamford Downtown to promote community connection, celebrate local talent, and enhance the vibrancy of our urban core. Each installation was thoughtfully designed to beautify sidewalks while encouraging spontaneous moments of delight. Stamford Downtown encourages our residents, visitors, employees and students to take a selfie with this artwork at tag @StamfordDowntown. Stamford Downtown will repost as many of these photos as possible. Download images of the Sidewalk Art Project here: https://www.dropbox.com/scl/fo/yqutsldnn3con3gcwc2g9/AIasGGlq16_ImF9INh-auc8?rlkey=crsa9zcu7l8nk17g8k2yunn9g&dl=0 Follow @StamfordDowntown and @8ballcreates on Instagram. About Chancellor Hayes Chandler finds immense satisfaction in transforming public spaces through art. His work on the Stamford Downtown Sidewalk Art Project has been a truly enriching experience for him; offering insights into the logistical dance of urban art – from exploring the city for ideal locations and scheduling painting days in the heat of summer, to discovering the perfect materials. With pieces like "Jump" and "Kiss Here" in Columbus Park, "Playground Club" at Latham, "Smile Here" in Kiwanis Park, and "What Will You Read Today?" at Ferguson Library, Chancellor has poured creativity into every design and concept. He cherishes the fun of this creative process and is enthusiastic about future opportunities to bring art to the community. 8ballcreates on Instagramon Instagram About Stamford Downtown Special Services District: Stamford Downtown Special Services District is responsible for creating, managing and promoting a quality environment for people, which enhances the economic vitality of Stamford Downtown. Stamford Downtown 
By Cathy Ithier August 13, 2025
Summer is at its peak in Fairfield County, presenting a diverse array of cultural and recreational activities for residents and visitors alike. This week’s calendar features an impressive lineup of live music performances, art fairs, food festivals, and outdoor events that offer something for every interest and age group. From captivating steel drum evenings at scenic vineyards to traditional bluegrass festivals and engaging beachside concerts, the region invites the community to experience the best of summer entertainment and relaxation. In addition, just under two hours away, the Sullivan Catskills region of New York honors a pivotal moment in music history—the 1969 Woodstock Festival , held from August 15 to 18. This year, Sullivan County is commemorating the festival’s legacy with a series of special tribute events and performances that pay homage to the birthplace of a cultural phenomenon. As an official partner of Sullivan Catskills, we are pleased to support the promotion of this distinguished destination and its revitalized appeal. Whether you’re planning a weekend escape or a seasonal retreat, we encourage you to explore the Sullivan Catskills to experience its rich heritage, vibrant arts scene, and breathtaking natural beauty. Discover more about upcoming events and plan your visit today to connect with the legacy of Woodstock and create unforgettable memories. Find out more about the Catskills here.
By Cathy Ithier August 12, 2025
Get ready to laugh your way through autumn! The Palace Theatre Stamford is bringing the heat this fall with a knockout lineup of comedians that promise to deliver the perfect blend of wit, charm, and side-splitting hilarity. The season kicks off on October 10 with viral sensation Trey Kennedy , followed by comedy legends John Cleese and Anthony Rodia —three unique shows, each guaranteed to leave you grinning.
By Cathy Ithier August 10, 2025
Get ready for a night of Southern rock grit and bluesy soul when Parker Barrow takes the stage at The Palace Theatre Stamford on Friday, September 19 . Fronted by powerhouse duo Megan Kane (vocals) and Dylan Turner (drums), and joined by Alex Bender (guitar), Will Tipton (guitar), Bo Howard (bass), and Eric Safka (keys), Parker Barrow delivers a high-energy show that’s equal parts heart, swagger, and musicianship. Whether performing as a 6-piece or expanding to a 10-piece ensemble, the band’s sound is bold and unforgettable. Inspired by the infamous outlaw couple Bonnie Parker and Clyde Barrow , Kane and Turner aim to embody that same fierce connection and adventurous spirit—only this time, in pursuit of their rock ’n’ roll dreams. Blending influences from The Black Crowes , Allman Brothers , Tedeschi Trucks Band , and Whiskey Myers , Parker Barrow infuses every performance with blues-rich storytelling and Southern rock fire. Their chemistry on stage, fueled by faith and a love for the road, makes each show feel personal and electric. From intimate acoustic sets to full-blown rock showcases, Parker Barrow is a rising band that’s blazing its own trail—and leaving a lasting impression with every performance. 🎟️ Don’t miss Parker Barrow live at The Palace Theatre Stamford on September 19. Get tickets at palacestamford.org.
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