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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)


Westport, CT - Verso Studios, the media arm of The Westport Library, is excited to announce its first-ever Battle of the Bands , an electrifying live music event celebrating the next generation of Fairfield County talent. Taking place Saturday, January 10, in the Library’s incomparable Trefz Forum, the high-energy showcase will feature four standout teen and college-aged bands: The Breakers, Clockwork, Caravan, and MOSS . Doors open at 7 pm , with the show beginning at 8 pm . Tickets are $10 for students and $20 for general admission, and can be purchased here . More than just a concert, this interactive competition puts the outcome entirely in the hands of the audience. Attendees will vote at the end of the night to determine the winner, awarding a $500 grand prize to first place and $250 to second place. Verso Studios is dedicated to amplifying creativity, collaboration, and community, and the debut of this Battle of the Bands marks an exciting new initiative in support of local live music. The event brings together emerging artists and music fans for a night that celebrates original sound, high-energy performance, and grassroots support for the local music scene. Whether attendees come to support a favorite band or discover something new, the event promises an unforgettable experience where community engagement plays a central role. Event Details Location: Trefz Forum, The Westport Library, 20 Jesup Road, Westport, CT 06880 Doors: 7 pm Show: 8 pm Bands: The Breakers, Clockwork, Caravan, MOSS Audience-voted competition with cash prizes Tickets and additional information: https://westportlibrary.org/event/verso-studios-presents-battle-of-the-bands/

Brookfield Film Festival: A Small Town with a Big Film Legacy Brookfield, CT - Brookfield, Connecticut may be a small town, but it holds a meaningful place in the regional film community. Located in Fairfield County within the southern foothills of the Berkshire Mountains, Brookfield is bordered by Candlewood Lake and Lake Lillinonah and sits just 43 miles northeast of New York City. With a population of approximately 17,000, the town has become a welcoming hub for independent filmmakers. Now in its 18th year, the Brookfield Film Festival continues to gain momentum inside the historic Brookfield Theatre for the Arts. Sponsored by the all-volunteer Brookfield Arts Commission, the festival not only celebrates independent film, but also supports arts education. Proceeds benefit the Brookfield Arts Commission Arts Scholarship Award, presented annually to a graduating Brookfield high school senior pursuing a degree in the arts. This year’s two-day festival features four curated program blocks. Regional Indie Afternoon showcases films from Connecticut and neighboring states, followed by filmmaker Q&A discussions. Read-Through Indie Morning, presented with the Brookfield Theatre for the Arts, gives screenwriters the opportunity to hear their work read aloud and network with actors and filmmakers in a collaborative setting, complete with complimentary coffee and pastries. Shorts and to the Point highlights a handpicked selection of Oscar-nominated and award-winning short films, while Music Indie Evening features original music videos from regional artists and filmmakers. The Brookfield Film Festival takes place March 27 through March 29 at the Brookfield Theatre for the Arts, located at 184 Whisconier Road in Brookfield, CT. A $15 suggested donation supports festival programming and scholarships. Light refreshments and festival merchandise will be available throughout the weekend. With its intimate atmosphere, diverse programming, and strong community focus, the Brookfield Film Festival proves that big creative impact can come from a small town.

Stamford, Ct - Stamford Downtown is excited to announce the return of the beloved Fire & Ice Winter Festival , bringing warmth, artistry, and winter fun back to Columbus Park on Saturday, January 24, 2026, from 1:00 to 5:00 PM . A favorite seasonal tradition, Fire & Ice offers a dynamic afternoon for all ages. Visitors can gather around cozy fire pits, watch live ice sculpting demonstrations by talented professional artists, and enjoy live music throughout the park. Nearby Columbus Park restaurants will add to the experience with inviting indoor and outdoor dining options, creating a lively and welcoming winter atmosphere. This FREE community festival celebrates the best of winter in Stamford Downtown—bundled-up fun, glowing fires, sparkling ice, and shared moments. Don’t miss this signature winter event!




