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"Can't-Miss Concerts, Festivals, & Fairs in and around Fairfield County: Your Ultimate Guide to Summer Fun!"
Local summer concerts may be winding down, but the fun isn’t stopping! 🍉🎶 With festivals, carnivals, and plenty of fruit and vegetable picking in full swing, this week is packed with events across the region. 🌻🎡 Whether you’re in the mood for some live music, want to indulge in delicious food, or looking for a family-friendly day out, we’ve got you covered. Pick your town, pick your event, click for updates, and GO! 🚗✨
Tuesday, August 20
- Bridgeport: Tangled Vine – St. Ann’s Church – 481 Brewster St (6:30-8:30pm)
- Derby: Silver Steel Band – Derby Green – 105 Elizabeth St (7-9pm)
- Newtown/Sandy Hook: NYC's Jazzy R&B Soulful Sounds & Wine – Aquila's Nest Vineyards – 56 Pole Bridge Rd (6pm-9pm)
- Norwalk: Open Jam in Freese Park (7-10pm)
- Oxford: Nashville Drive – Jackson cove Town Park – 98 Jackson Cove Rd (6:30pm)
- Ridgefield: Sue Foley Trio – Ballard Park – 485 Main St (7-9pm)
- Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stratford: Afinke Band – Paradise Green – 121 Huntington Rd (7pm)
- Trumbull: Floydian Trip – Trumbull Town Green & Gazebo – 5866 Main St (7pm)
- Westport: LaMP (Russ Lawton, Scott Metzger, Ray Paczkowski) - Levitt Pavilion – 40 Jesup Rd (7pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-10pm)
Wednesday, August 21
- Danbury: San Gennaro Festival – Danbury City Center Green – 1 Ives St (5-11pm)
- Greenwich: Billy and The Showmen – Roger Sherman Baldwin Park – 100 Arch St (7pm)
- New Canaan: Fairfield Counts Band – Waveny Park – 677 South Ave (7:30pm)
- Norwalk: The Sound Waves – Pinkney Park – 177 Rowayton Ave (5:30 pm)
- Norwalk: The Stevie Experience – Calf Pasture Beach – Calf Pasture Rd (7:30pm)
- Shelton: The Bernadettes – Shelton Huntington Green – Huntington St. (7pm)
- Southbury: Deuces Wild Duo – River Glen Health Care Center – 162 S. Britain Rd (6:30pm)
- Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stamford: Comedian Heather Shaw – New York Comedy Club Stamford – 230 Tresser Blvd (7pm)
- Westport: Lobesterfest at Campo Beach (3-7pm)
- Westport: Miss Tutti & The Fruity Band – Children's Series –Levitt Pavilion 40 Jesup Rd (7pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-10pm)
Thursday, August 22
- Bridgeport: Impractical Jokers – Hartford HealthCare Amphitheatre – 500 Broad St (7:30pm)
- Brooklyn: Brooklyn Fair – 15 Fairgrounds Rd - (4pm-11pm)
- Danbury: San Gennaro Festival – Danbury City Center Green – 1 Ives St (5-11pm)
- Fairfield: Donavon Frankenreiter – The Lot at FTC – 70 Sanford St (8pm)
- Greenwich: Sun Kings (A Beatles Tribute) - Greenwich Historical Society – 47 Strickland Rd (6:30pm)
- New Fairfield: Split Decision Band – New Fairfield Gazebo – Rt 39 (6:30pm)
- New Milford: The Pop Rocks – Downtown New Milford – 25 Main St (6:30-8:30pm)
- Newtown/Sandy Hook: Sean McNamara Duo – Aquila's Nest Vineyards – 56 Pole Bridge Rd (5:30-8:30pm)
- Newtown/Sandy Hook: Wine & Wheels Car Show – Aquila's Nest Vineyards – 56 Pole Bridge Rd (6pm)
- Orange: West Rocks – Orange Fairgrounds – 525 Orange Center Rd (6-8pm)
- Ridgefield: The Steel Wheels – Ballard Park – 485 Main St (7-9pm)
- Stamford: Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stamford: Fred & Ethal – Street Beats – Bedford Street (6-8pm)
- Stamford: The Mojomatics – Street Beats – Columbus Park – Main St (6-8pm)
- Stamford: Vicky Dussich & Friends – Street Beats – Lower Summer St (6-8pm)
- Stamford: Comedian Ahren Belisle “America's got Talent” - New York Comedy Club Stamford – 230 Tressler Blvd (7pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-10pm)
Friday, August 23
- Bridgeport: John Goode – National Association of Naval Veterans – 69 Brewster St. (5:30-8:30pm)
- Bridgeport: Tedeschi Trucks Band w/special guest Margo Price – Hartford HealthCare Ampitheater – 500 Broad St. (7pm)
- Brookfield: Dan’s Garage – Brookfield Town Hall – 100 Pocono Rd (6:30pm)
- Brooklyn: Brooklyn Fair – 15 Fairgrounds Rd - (10am-11pm)
- Chester: Chester Fair – 11 Kirtland Terrace (6pm-11pm)
- Danbury: San Gennaro Festival – Danbury City Center Green – 1 Ives St (5-11pm)
- Newtown/Sandy Hook: Filo Fox – Aquila's Nest Vineyards – 56 Pole Bridge Rd (6pm)
- Newtown/Sandy Hook: Family Glow Nights – Aquila's Nest Vineyards –56 Pole Bridge Rd (6:30pm)
- Shelton: Dan Carlucci – Jones Family Farms – 606 Walnut Tree Hill Rd (5-7pm)
- Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stamford: Comedian Aida Rodriguez – New York Comedy Club Stamford –230 Tresser Blvd (7pm & 9:30pm)
- Westport: Steve Keith – Music on Church Lane (6pm-9pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-10pm)
Saturday, August 24
- Black Rock: PorchFest at Norden Club – 4 Seabright Ave (11am – 8pm)
- Bridgeport: Skateport Roller Skating Event – 1155 Main St (4pm-8pm)
- Bridgeport: Tedeschi Trucks Band w/special guest Margo Price – Hartford HealthCare Ampitheater – 500 Broad St. (7pm)
- Brooklyn: Brooklyn Fair – 15 Fairgrounds Rd - (9am-11pm)
- Chester: Chester Fair – 11 Kirtland Terrace (8am-11pm)
- Clinton: SummerFest & Fireworks – 1 Waterside Lane (4pm-9pm)
- Danbury: San Gennaro Festival – Danbury City Center Green – 1 Ives St (1-11pm)
- Fairfield: Greenfield Hill Grange Agricultural Fair – 1873 Hillside Rd (10am-3pm)
- Fairfield: DNR – Sherman Town Green – 1451 Post Rd (6:30pm)
- Newtown/Sandy Hook: Tony & The West Siders – Aquila's Nest Vineyards – 56 Pole Bridge Rd (2:30-5:30pm)
- New Haven: International Cultural Arts Fusion Festival – Edgewood Park –Edgewood Ave (11am-5pm)
- New Milford: ACE & Friends – New Milford Town Green – 25 Main St (7pm)
- Norwalk: Pisani Music Co ft. Ms. Rhonda Denet – Calf Pasture Beach (7pm)
- Southbury: CT Arts & Eats – Southbury Town Hall – 501 Main St. S (10am-4pm)
- Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stamford: Comedian Je Devito – New York Comedy Club Stamford – 230 Tessler Blvd (7pm)
- Stamford: Comedy Showcase with Kristal Adams, Maximilian Spinelli, J.P. Mcdade, Max Antonucci at New York Comedy Club Stamford - 230 Tresser Blvd (9:30pm)
- Westport: Madelyn Spera – Church Lane (6pm-9pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-10pm)
Sunday, August 25
- Bridgeport: Ear Candy Duo – National Assoc. Of Naval Vets – 69 Brewster St (3pm)
- Brooklyn: Brooklyn Fair – 15 Fairgrounds Rd - (9am-6pm)
- Chester: Chester Fair – 11 Kirtland Terrace (9sm-6pm)
- Danbury: San Gennaro Festival – Danbury City Center Green – 1 Ives St (1-10pm)
- Greenwich: Sound Beach Community Band – Binney Park – 130 Arch St (7pm)
- Milford: Avenue Groove Band – Walnut Beach Pavillion – 353 E Broadway (4pm-7pm)
- Newtown/Sandy Hook: Frandango Trio – Aquila's Nest Vineyards – 56 Pole Bridge Rd (2:30-5:30pm)
- Newtown/Sandy Hook: Comedian Carmen Lagala – Aquila's Nest Vinewards – 56 Pole Bridge Rd (7pm)
- Norwalk: The Barons – Calf Pasture Beach (5pm-7pm)
- Norwalk: Magic – Pinkney Park – 177 Rowayton Ave (5:30pm)
- Redding: Floydian Trip (Pink Floyd) - Redding Town Green – 15 Cross Hwy (6pm-8pm)
- Shelton: Danny Trzcinski – Jones Family Farms – 606 Walnut Tree Hill Rd (2pm-4pm)
- Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stamford: Sun Kings – Bartlett Arboretum – 151 Brookdale Rd (5-7pm)
- Stamford: Very Good Comedy ft: Lorrie Brownstone, Aric Grooms, Sheba Mason, Robert Punchur at New York Comedy Club Stamford-230 Tresser Blvd (7pm)
- Trumbull: Bob Button Band – Trumbull Town Hall & Gazebo – 5866 Main St (4pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-8pm)


America’s Top Lifestyle Expert Debuts Deeply Personal One-Man Show Benefiting Survivors of Domestic Violence Westport, CT: Mar Jennings, an Emmy®-nominated, nationally syndicated television host, award-winning Realtor, entrepreneur, philanthropist, and influencer, adds storyteller and performer to his dynamic career with “Mar Jennings — ONE-MAN SHOW”, a powerful and deeply personal production debuting May 22, 2026, at Sacred Heart University Community Theatre. This one-night-only performance is expected to sell out quickly. In a meaningful commitment to community impact, 100% of the proceeds will benefit The Center for Family Justice, supporting survivors of domestic violence, abuse, and trauma, with a fundraising goal of $200,000 going directly to the cause. “This chapter is about truth, legacy, and using my story for something bigger than myself,” says Jennings. “When I realized this show could raise real money for charity, it gave the project a deeper purpose. I’m ready to share my story now in a way I simply wasn’t before.” Years in the making, the production reflects both a lifetime of experiences and a turning point toward giving back in a more profound way. The result is a deeply human performance that balances vulnerability with purpose. Blending storytelling, humor, and raw honesty, Jennings shares a journey of resilience, reinvention, and hope, offering the audience an intimate, unfiltered look at overcoming life’s most difficult moments. “The hardest part is choosing what to reveal and what to hold sacred,” Jennings shares. “But if my story helps someone feel less alone, then every moment of discomfort is worth it.” Mar Jennings — ONE-MAN SHOW promises to be emotional, inspiring, and unforgettable, designed to create a genuine connection between performer and audience, reminding people that hope is real, that healing is possible, and that none of us are alone in the dark. "Mar’s decision to speak publicly about his journey marks an important moment, and we are grateful for his trust,” says Mark Antonini, President & CEO of The Center for Family Justice. “His voice will resonate with so many, and we are fully committed to supporting him and ensuring the success of this meaningful event.” “I’m ready to tell the whole story—the real one,” says Jennings. “If my journey can become a spark for someone else… if my pain can be transformed into power for others… then it all means something.” About Mar Jennings Mar Jennings is a nationally recognized lifestyle expert, bestselling author, television host, and speaker known for home design, entertaining, and lifestyle transformation. He is also a top-producing real estate professional and founder of The Mar Jennings Team, bringing his signature Casual Luxury® approach to every listing. Jennings uses his platform to inspire connection, positive change, and support for survivor advocacy. About The Center for Family Justice The Center for Family Justice provides crisis intervention, safe housing, counseling, and advocacy for survivors of domestic violence, sexual violence, and child abuse—helping individuals rebuild their lives with dignity and hope. Event Details Mar Jennings — ONE-MAN SHOW May 22, 2026 Sacred Heart University Community Theatre, Fairfield, CT Tickets: $54 http://shucommunitytheatre.showare.com/MarJenningsOne-ManShow

A one-of-a-kind alcohol-free wellness dance experience showcasing elevated mocktails, mindful connection, and vineyard sunsets. NEWTOWN, CT — Aquila’s Nest Vineyards, Connecticut’s award-winning experience-focused vineyard and event venue, is redefining what a night out at the vineyard can look like with its upcoming “Sunset Session: Sober Silent Disco in the Vineyards.” This immersive golden-hour event invites guests to dance beneath the open sky with wireless headphones, curated music channels, breathtaking vineyard views, and a refreshing lineup of handcrafted mocktails and non-alcoholic beverages. Hosted in partnership with Autumn Fletcher, the event offers a vibrant alcohol-free social experience designed for guests seeking connection, movement, and joy in a mindful atmosphere. As the sun sets over the vines, attendees will sip beautifully crafted zero-proof drinks while enjoying the peaceful magic of the vineyard in a completely new way. “At Aquila’s Nest, we are proud to offer more than wine—we create experiences for every lifestyle and every guest ,” said Neviana Zhgaba, Co-Founder of Aquila’s Nest Vineyards. “From our signature mocktails to wellness gatherings, silent discos, yoga, and live music, we want everyone to feel they can fully enjoy the beauty of the vineyard in a way that feels right for them.” The Sunset Sober Silent Disco is part of Aquila’s Nest’s growing portfolio of inclusive experiences that showcase the vineyard as a destination for wellness, celebration, creativity, and community . Guests can expect an unforgettable evening where vineyard sunsets meet music, movement, and sophisticated zero-proof offerings that prove the vineyard experience extends far beyond the wine glass. The event will take place on Wednesday, May 27, 2026, from 7 PM to 8:45 PM , Early arrival is encouraged to enjoy mocktails before the sunset silent disco in the vines begins. For tickets and details, visit: Reserve Your Sunset Silent Disco Experience

Westport, CT - The Westport Downtown Association, Inc. (WDA) presents Fashionably Westport for the sixth year, an evening that brings together fashion, community, and philanthropy in support of Homes with Hope. This year’s event promises an elevated yet intimate experience, featuring over twenty local boutiques, seven salons, and a dynamic lineup of 90 models. The Westport community is looking forward to coming together once again to celebrate this hometown event while supporting a meaningful cause. “The WDA is excited to host our 6th annual Fashionably Westport in support of Homes with Hope,” said Maxwell Crowley, President of the WDA. “It’s a great opportunity to bring the community together while highlighting and supporting our local businesses.” The event will be held at the Westport Library on Saturday, April 25th, from 7 to 10 p.m. Event Information: Visit the official event website Tickets: Purchase tickets on Eventbrite The WDA is honored to welcome Lonnie Quinn as co-emcee. Lonnie is an Emmy Award-winning meteorologist and has served as the Chief weathercaster for CBS News New York since 2007. A Westport resident, Quinn brings both energy and local connection to the evening. The WDA is excited to welcome back Dave Briggs as co-emcee. Briggs is a former CNN, NBC Sports, Fox News, and Turner Sports anchor. He has lived in Westport with his family since 2008. Finally, the WDA is excited to welcome the return of Carey Price , owner of Westport-based The Cove Collective, as runway director. Price is a Parsons School of Design alum with experience working alongside top fashion designers. No charity event is complete without a silent auction. The proceeds will benefit Homes with Hope. In 2024, the WDA raised $20,000, and hopes to exceed that goal this year. This year, the local business community has shown up in a big way, with over 100 donations. The silent auction is not to be missed. Explore all of the generous silent auction donors here , and stay tuned as the auction goes live on April 25, 2026, at 6:00 p.m.

Stamford, CT — Brews on Bedford, presented by Stamford Downtown, returns on Saturday, May 30 from 2–5pm in Latham Park on Bedford Street, featuring craft beer. Tickets are on sale now through Afton . Guests can fill a sampling glass with beer from a variety of regional breweries while enjoying live music, lawn games, and local food vendors. Participating breweries include: Berlinetta Brewing, Best Friends Lunch, Captain Zig, Delta Seltzers, Greenwich Brewing Company, Half Full Brewery, Hop & Vine Tap Room, Nod Hill Brewery, Twelvenote Brew Co, Whalers and more to come! General Admission Tickets for Brews on Bedford are $30 for Early Birds until April 20, so get your tickets now! A limited number of VIP tickets are available for an additional $10, granting early entry at 1pm (VIP hours: 1–5pm). The entry fee includes a tasting glass, unlimited samples (while supplies last) and entertainment. All guests must be 21 or older. Valid ID is required for admission, including: A current motor vehicle operator’s license A state-issued identity card A valid passport or Global ID accompanied by another form of photo ID Digital IDs are not accepted. Please drink responsibly and know your limits. No pets or children under 21 will be admitted. Brews on Bedford is presented by Stamford Downtown and supported by Hey Stamford! and Star 99.9. For more information, visit Stamford Downtown Brews on Bedford and to purchase tickets, visit: BrewsonBedfordTicketsatAfton



