This Week in Fairfield County: Live Music, Legendary Concerts & Summer Fun

New Canaan, CT: The inaugural New Canaan Music Festival held at The New Canaan Nature Center on Saturday September 19th 2026 will feature a reunion of NYC original rock band The Telephones, Mind the Gap, Pretty Nasty, Take A Step Back, and DMR Big Band on the main stage. The festival stage will welcome The Parkway Ramblers, Mokra, Otis & The Hurricanes, Peter and His Band of Wolves and also include an acoustic kid's concert “Not for Kids Only”. This event, presented by Michael-Louis Smith Music in partnership with the New Canaan Nature Center will bring the community together to enjoy great live music and family fun including activities for families with children, food trucks, beverages, festival merchandise, and other vendors. The 40-acre New Canaan Nature Center features two miles of walking paths, ponds, a cattail marsh, gardens and an apple orchard. The New Canaan Nature Center is located at 144 Oenoke Ridge, New Canaan, CT. Gates will open Saturday September 19th at 11am, music will begin at 12pm and performances will run until 10pm. This event is rain or shine, and guests are encouraged to bring a portable chair. No overnight camping will be permitted. Tickets and V.I.P. Packages are available at www.newcanaanmusicfestival.com

Newtown, CT: Aquila's Nest Vineyards is proud to announce that it has been named the #5 Best Wine Tasting Room in the United States in the prestigious USA TODAY 10Best Readers' Choice Awards, making it the highest-ranked wine tasting room in New England and the only winery in the region to earn a place in the national Top 10. The annual USA TODAY 10Best Readers' Choice Awards recognize exceptional destinations across the country through a combination of expert nominations and public voting. Aquila's Nest Vineyards stood alongside some of the nation's most celebrated wineries, earning recognition for its memorable guest experiences, hospitality, and unique approach to wine tourism. "This recognition is incredibly meaningful because it comes directly from the people who have visited us, celebrated life's special moments with us, and supported our journey," said co-founder Neviana Zhgaba. "To be recognized among the best wine tasting rooms in America—and to represent New England on this national stage—is an honor beyond anything we imagined." Founded by husband-and-wife team Neviana Zhgaba and Ardian Llomi, Aquila's Nest Vineyards has become one of Connecticut's premier wine destinations by combining award-winning wines with immersive guest experiences. The vineyard is known for its scenic views, themed outdoor seating, live music, comedy shows, seasonal events, wine pairings, educational programs, and welcoming atmosphere that encourages guests to relax, connect, and create lasting memories. "We've always believed that great wine is only part of the experience," said co-founder Ardian Llomi. "Our goal has been to create a place where people feel welcome, celebrate together, and leave with memories they'll want to relive. This award belongs to our incredible team and every guest who has supported us over the years." The recognition adds to Aquila's Nest Vineyards' growing list of national and regional honors, including being named Connecticut Magazine's Best Vineyard in Connecticut for multiple consecutive years, 2025 National Small Producer Winery of the Year by the Libation National Wine Competition, 2024 Connecticut Manufacturer of the Year by the U.S. Small Business Administration, and one of the U.S. Chamber of Commerce's Top 70 Small Businesses in America in 2023. Located in the scenic hills of Newtown, Connecticut, Aquila's Nest Vineyards welcomes visitors year-round to enjoy handcrafted wines, estate vineyard views, signature tasting experiences, private events, and an ever-changing calendar of entertainment. "We are deeply grateful to everyone who voted for us," added Zhgaba. "This achievement inspires us to continue raising the bar and creating unforgettable experiences for every guest who walks through our doors." For more information, visit www.aquilasnestvineyards.com or follow Aquila's Nest Vineyards on social media.

FAIRFIELD, CT: The Jamie Hulley Arts Foundation will celebrate its 24th Annual Evening for the Arts Gala on Saturday, September 19, 2026, at Fairfield University's Quick Center for the Arts, featuring Jay Stollman's Groovin' On Tour: A Woodstock Generation Rock Experience. The evening's featured performance will take audiences on a nostalgic musical journey through the unforgettable songs and artists that defined the late 1960s and early 1970s. The high-energy concert celebrates the music, memories, and spirit of the Woodstock generation. "This concert features a collection of the iconic songs that became the soundtrack for life in the late 1960s and early 1970s," said Foundation Director Judy Primavera. "Purchase tickets early as we are likely to sell out." The gala begins with a reception and raffle preview at 6:30 p.m., featuring light refreshments, followed by the concert at 7:30 p.m. Advance tickets are $50, or $60 at the door. More than an evening of great music, the gala is the Foundation's signature fundraising event, with 100% of proceeds supporting scholarships, educational programs, and artistic opportunities for young people throughout Connecticut. Founded in 2002 in memory of Jamie Alaine Hulley, the Jamie Hulley Arts Foundation remains committed to inspiring the next generation of performers, musicians, visual artists, and creative professionals. Tickets are available through the Fairfield University Quick Center for the Arts Box Office by calling (203) 254-4010 or visiting quickcenter.fairfield.edu/box-office.

Milford CT: -For more than five decades, families from across Connecticut, New York, Long Island, and beyond have made their way to Milford each summer to experience one of the state’s longest-running coastal fair traditions. The Downtown Milford Business Association (DMBA) announces the official entertainment lineup for the 2026 Fair on the Half Shell, returning to the Historic Milford Green on Saturday, August 15, from 9 a.m. to 5 p.m., bringing together more than 300 artisans and makers, 20+ food trucks, family attractions, environmental exhibits, and interactive experiences, all with free admission and sponsored by United Illuminating (An Avangrid Company) and Loyal Nine Cocktail Co. The 2026 music lineup features locally recognized musicians, regional favorites, and emerging Connecticut talent, with Caribbean songs, rock, pop, country, and acoustic sets scheduled throughout the Fair from morning through late afternoon. 2026 Entertainment Schedule ● The Steel Drum Band ● The Rashaan Langley Project ● Shot Down ● Hazard County From music to marketplace, Fair on the Half Shell brings live entertainment, small business commerce, and coastal culture together in one walkable downtown setting, drawing thousands of visitors from across the Northeast and positioning Milford as a key summer day-trip destination, accessible by boat via Milford Harbor, train via Metro-North Railroad, and car via Interstate 95 and the Merritt Parkway. Plan your visit by adding the event to your digital calendar via Eventbrite to be automatically entered into the official Fair on the Half Shell Giveaway, which includes Fair merchandise, downtown Milford gift cards, and more. Add to Your Calendar: https://www.eventbrite.com/e/fair-on-the-half-shell-2026-forme rly-oysterfest-fair-ct-summer-festival-tickets-1992095795149 Event Date: August 15, 9am to 5pm Location: Milford Green | 84 Broad Street, Milford, Connecticut 06460 Admission: FREE

Rain is in the forecast later today, so be sure to check directly with each event organizer before heading out. Some outdoor concerts may move indoors or be rescheduled. Looking for a Plan B? Fairfield After Dark has plenty of options this week, including karaoke , trivia , open mic nights , comedy shows , and live music throughout Connecticut and Westchester County . Thursday: Enjoy free live music at Aquila's Nest Vineyards , Family Trivia Night at O'Deen's at Oak Hill s, or catch Fuzz on It at Brass & Bone . Friday: Mike Milazzo performs on the porch at O'Deen's Ridgefield , Valerie Rose takes the stage at Aquila's Nest Vineyards , Tristan Connolly brings jazz to Brass & Bone , Drew Angus performs at Bedford Playhouse , and comedian Chris Kattan headlines four shows at New York Comedy Club Stamford . End the night with Downstairs Joe at Brass & Bone. Saturday: Don't miss the Hey Stamford Food Festival at Mill River Park or Connecticut's inaugural Country Music Festival at the North Haven Fairgrounds featuring host Taylor Hicks, Annie Bosko, Mark Mackay, Morgan Myles, Kristen Brown, and regional favorites. Save 10% with promo code FAD10 . Then head to The Palace Danbury for Mamma Mania: The American Tribute to ABBA. Sunday: Wrap up the weekend with Flying Ivories Dueling Pianos at Aquila's Nest Vineyards , Sundays with Scott at Brass & Bone , Connecticut Pizza & Brew Fest at The AMP in Bridgeport, or another night of laughs at New York Comedy Club Stamford . A special shout-out to the Connecticut Country Music Festival for assembling an outstanding lineup of national and regional artists. Giveaway winners have been announced, but you can still save 10% on tickets with promo code FAD10 . See you there! Tuesday, July 28, 2026 ☀️🎶Bridgeport: Brotherhood - Black Rock Concert Series (6:30pm – 8:30pm) Milford: Jazz Record Mingle at Milford Arts Council(6pm - 9pm) 🎶 🎤 Monroe: Family Character Night: tom Weber with Hello Kitty & Micky Mouse at Great Hollow Lake(5:30pm - 7pm) New Canaan: Tuesday Night Jazz with Noreen Mola Quartet at Roger Sherman Inn(6pm - 8:30pm) ☀️🎶Newtown: Michele Urban at Newtown Kids Concerts at Dickinson Memorial Bandshell(11am –12pm) ⭐🍽️ 🎤✨Norwalk: OPEN MIC NIGHT AT BRASS & BONE(8pm) ☀️🎶Oxford: The Potentials - Oxford Summer Nights At The Beach(6:30pm) ☀️🎶Stratford: Kathy Thompson Band Outside on the Paradise Green Gazebo (7pm) Stamford: Maria Tiscia is Rio Bound at Villa Italia Restaurant(6:30pm) ☀️🎶Trumbull: Steve Elci & Friends at Trumbull’s Summer Kids Concert Series(10-11am) ☀️🎶Trumbull: Number 9 at Trumbull Gazebo Tuesday Night Concert Series (7pm) Wednesday, July 29, 2026 Bethel: Jon Garcia & CLAVE Afro-Rican Jazz Ensemble On The Patio... Everyone Salsa! at La Zingara Restaurant(7pm - 9pm) ☀️🎶Danbury: Kristin O'Conner Vece at St. James Episcopal Church(12pm) ☀️🎶Fairfield: Steve Elci & Friends perform at Fairfield's Peanut Butter Jam Concerts at Sherman Green(10:15am) Fairfield: Music with The Lamb Jam at The Seagrape Fairfield(8:30pm) Greenwich: Gunsmoke-Country at Roger Sherman Baldwin Park (7pm) Mt Kisco, NY: Mar Jennings ONE MAN SHOW – Reading(6pm - 8pm) ☀️🎶New Canaan: The Bookends – 60’s and 70’s Songs at Waveny Park(7:30 – 9:30pm) ⭐🎟️🪴Newtown: Plant Bingo at Aquila's Nest Vineyards(6pm) Norwalk: Detroy Langer & Riccio Organ Trio at Greer Southern Table(6pm - 9pm) ⭐🍽️🎙️🎶Norwalk: KARAOKE Party at BRASS & BONE(8pm) Piermont, NY: Spyro Gyra Jazz featuring Jeremy Wall at OTTO'S(6pm - 9pm) ☀️🎶Shelton: Alligator - Shelton Music under the stars Summer Concert Series (7pm) Shelton: Billy Solo at Spotted Horse Tavern(8pm) Stratford: Bruce 3 The Human Jukebox at Joey C's Boathouse Cantina & Grill(5:30pm - 8:30pm) ⭐😂🎟️Stamford: Shannon Fiedler, Beau McDowell, Ish Gupta, Cody Marino at New York Comedy Club Stamford (7pm) Thursday, July 30, 2026 ☀️🎶Bridgeport: Sammulous Sammulous + AffinitiNYC affinity nyc at McLevy Green (6pm – 8:45pm) ☀️🎶Bridgeport: Bobby Wheeler at Captain's Cove Seaport (Marina, Restaurant & Bar) (5pm - 9pm) ☀️🎶Fairfield: Green Eyed Lady (Classic Rock, Soul, 70's, 80's, 90's) at Sherman Green Gazebo (6:30pm –8pm) Milford: Calliopi at Cafe Atlantique(5pm) Milford: HAVANA NIGHT at Stonebridge Restaurant(5:30pm) ⭐🎶🆓Newtown: Ode To Rosie at Aquila’s Nest Vineyard (5:30-8:30pm) ⭐🎟️Newtown: Tarot Reading with Abriella at Aquila's Nest Vineyards(5:30pm) ⭐🎟️🧘Newtown: Yoga in the Vineyard at Aquila's Nest Vineyards(6:30pm) ☀️🎶Newtown: Echoes of Sinatra at the Dickinson Memorial Bandshell - Newtown (6:30pm –8pm) ⭐🍽️ 🎶Norwalk: Fuzz on it at Brass & Bone(9pm) 🍔🍺🧠 Norwalk: Trivia Night at Odeen’s at Oak Hills (7-9pm) Port Chester, NY: Snarky Puppy with Medeski + Martin Duo at The Capitol Theatre(8pm) Rye Brook, NY: Logical Pretzel Steely Dan Tribute(7pm) Shelton: Only Child at Spotted Horse Tavern(8pm) Stratford: FLANNEL CLAD masses at Blackbird's Nest(6pm) Stratford: Tangled Vine at Joey C's Boathouse Cantina & Grill(6:30pm) ☀️🎶Stamford: Ja Rule & Ashanti - Summer In The Park(7pm) ⭐😂🎟️Stamford: Vannessa Jackson, Levi White, JC Mendoza, Ian Hunt at New York Comedy Club Stamford(7pm) ☀️🎶Wilton: Everything Else - Wilton Library Summer Music Concert in the Brubeck Room(5pm –6:30pm) Westport: Latin Jazz for a Summer Night with Michael Mossman at Jazz Society of Fairfield County, Inc.(7:30pm - 10pm) Westport: Music with Billy Genuario Spotted Horse Tavern(9pm) Friday, July 31, 2026 Bethel: Old School 203 at Broken Symmetry Brew(6pm) Bethel: Remnants at Dragonfly(6pm - 9pm) Bethel: Bourbon Honey at Shakedown Street Eats(6:30pm) Bedford, NY: Drew Angus at Bedford Playhouse(6:30pm) ☀️🎶Brookfield: TALES OF JOY at the Summer Concerts in the Park - Brookfield(6:30pm) ☀️🎶Bridgeport: Ariana - Friday Night Music on the Dock at Port 5(5pm –8:30pm) ☀️🎶Bridgeport: Hesitation Blues Band at Twelvenote Brew Co.(7pm - 10pm) ☀️🎶Bridgeport: Billy Lopez at Captain's Cove Seaport (Marina, Restaurant & Bar)(5pm - 9pm) Bridgeport: Faster Things Band - Allman Brothers Tribute at Park City Music Hall(7pm - 11pm) Bridgeport: Late 4 Dinner atThe Castle, Black Rock(8pm - 11pm) Danbury: Muddy River Blues (Blues) at Danbury City Center Green(7pm – 9:30pm) Danbury: Joey Whalen at Charter Oak Brewing and Taproom(7pm - 9pm) Danbury: DJ JR at Elicit Brewing Co - Danbury(10pm) Milford: TWO OF A KIND at Stonebridge Restaurant(6pm) Milford: Jessie Mae at Cafe Atlantique(6:30pm) ☀️🎶Monroe: Shaded Soul - Monroe Arts in the Park Concerts(7pm) ⭐🎟️Newtown: Valerie Rose at Aquila's Nest Vineyards(5:30pm - 8:30pm) ⭐🎟️Newtown: Yappy Hour - Bring Your Furry Friends at Aquila's Nest Vineyards(6pm) ⭐🎟️💖Newtown: Cougar Night Speed Dating at Aquila's Nest Vineyards(7pm) Newtown: Tony & the West Siders at Reverie Brewing Company(6pm - 9pm) Norwalk: Category 5 at 314 beergarden(7:30pm - 10:30pm) Norwalk: Ray Simonelli at BanC House(8pm - 11pm) ⭐🍽️ 🎶Norwalk: Tristan Connolly at Brass and Bone(6pm) ⭐🍽️ 🎶Norwalk: Downstairs Joe at Brass and Bone(8:30pm) Old Greenwich: Kovac Brothers at Bosco's Bar and Grill(9pm - 12am) ⭐🍽️🎶Ridgefield: Mike Milazzo on the Porch at ODEEN'S Ridgefield(5;30pm - 8;30pm) Ridgefield: Old Bob at Nod Hill Brewery(6:30pm) Stratford: Tin Sandwich at Blackbird's Nest(6pm) Stratford: Not My Problem at Joey C's Boathouse Cantina & Grill(9pm) ⭐😂🎟️Stamford: Comedian Chris Kattan at New York Comedy Club Stamford (4 Shows)(7pm - 9:30pm) Stamford: The Tonic at Tiernan's Bar & Restaurant(9:30pm) Westport: Fake ID at Black Duck Cafe(9pm) ☀️🎶Westport: Dan Tressler - Music on Church Lane(5:30pm –9pm) Westport: Jonathan Niles Chapman at Walrus Alley(7:30pm - 10:30pm) Woodbury: Brian Dolzani as The Loner: The Music of Neil Young at Woodbury Brewing Company(8:30pm - 11pm) August 2026 Saturday, August 1, 2026 Bethel: DAN SAWYER at Whitlock's Restaurant(6pm - 9pm) Bethel: Barry From Bone Dry at Shakedown Street Eats(6:30pm) Bethel: Rob Glassman Band at NOTCH8(8pm) Bridgeport: Tony Fratuso at Boca Oyster Bar(5pm - 8pm) ☀️🎶Bridgeport: Rose Ganache at Twelvenote Brew Co.(7pm - 10pm) Brookfield: Rio Sorrentino at Pulcinella(7pm - 10pm) Danbury: Tony & The West Siders at Charter Oak Brewing and Taproom(4pm - 7pm) Danbury: Mojo/Sugar House at Sugar Hollow Taproom(8pm) East Haven: Bluegrass Jam at The Shore Line Trolley Museum(6pm - 8:30pm) ☀️🎶Fairfield: Whiskey & Rye at Fairfield's Sweet Sounds of Summer Concerts Series at Sherman Green (6:30pm) Greenwich: Fragments: The Musical Milieu of Georges Braque(2pm - 4pm) Hartford: Taste of the Caribbean Arts & Culture(1pm - 8:30pm) ☀️🎶Milford: Free Music at Walnut Beach Arch(4pm –6pm) New Milford: The Rakes at Housatonic River Brewing(7pm - 10pm) 🎟️👢 🎶North Haven: Connecticut Country Music Festival(1pm) ⭐🎟️Newtown: Sinatra & Dino Rat Pack Tribute Show at Aquila's Nest Vineyards(6pm) ⭐🎟️🍷🍪Newtown: Girls Scout Cookies and Wine Pairing at Aquila's Nest Vineyards(12pm) Newtown: Shakedown Saturday with Almost Ablaze at Reverie Brewing Company(6pm - 9pm) Norwalk: Badboy at 314 beergarden(7:30pm - 10:45pm) ⭐🍽️ 🎶Norwalk: Party with Friends at Brass and Bone(9:30pm) Old Greenwich: Liquid Courage at Bosco's Bar and Grill(9pm - 12am) Pawling, NY: Trouble No More at Daryl's House Restaurant & Music Club(8pm) Port Chester, NY: Old Crow Medicine Show with Deadgrass Celebrating Jerry Garcia's Birthday at The Capitol Theatre(8pm) Redding: Mystery Train at Milestone(9pm - 11:30pm) Ridgefield: The Hot Club of Black Rock at Nod Hill Brewery(5pm) Shelton: Junk at Spotted Horse Tavern(8pm) Stratford: Fake ID Band at Blackbird's Nest(6pm) Stratford: Rhythm City at Outriggers Restaurant(6pm - 9pm) Stratford: Pop Rocks at Joey C's Boathouse Cantina & Grill(9pm) ☀️🛍️Stamford: Hey Stamford Food Festival at Mill River Park(12pm –8pm) ⭐😂🎟️Stamford: Comedian Chris Kattan at New York Comedy Club Stamford (4 Shows)(7pm - 9:30pm) ⭐😂🎟️Stamford: Caroline Hanes, Victor Tran, Derek Humphrey, Colin Cab Washington at New York Comedy Club Stamford(4:30pm) Stamford: Sonic Bullet at Tiernan's Bar & Restaurant(9:30pm) ☀️🎶Westport: Vinnie Ferrone - Music on Church Lane(5:30pm –9pm) Woodbury: Pearl Jam Tribute - Last Exit at Woodbury Brewing Company(8:30pm - 11pm) Sunday, August 2, 2026 Bethel: She's My Ex at Broken Symmetry Brew(12pm) Bethel: Dead Set Jonny Chapman at Shakedown Street Eats(3pm) Bethel: Gumbo at NOTCH8(5pm) ☀️🎶Bridgeport: Hooch - Sunday Night Music on the Dock at Port 5(3pm) ☀️🍕Bridgeport: Connecticut Pizza & Brew Fest at Connecticut Pizza & Brew Fest(1pm - 4pm) ☀️🎶Bridgeport: Orb Mellon at Twelvenote Brew Co.(2pm - 5pm) Bridgeport: Johnny Hollywood at Boca Oyster Bar(5pm -8pm) Danbury: The BENT REEDS at Charter Oak Brewing and Taproom(3pm - 5pm) ☀️🎶Fairfield: Glamour Girls (Swing, Soul, & Pop) at Sherman Green Gazebo (6:30pm –8pm) ☀️🎶Milford: HYPE - Walnut Beach Pavillion(4pm –7pm) Milford: MADHOUSE at Stonebridge Restaurant(4:30pm) ⭐🎟️Newtown: Dueling Pianos with the Flying Ivories at Aquila's Nest Vineyards(6pm) ⭐🎟️🥂Newtown: Cheese Fondue Dip & Sip at Aquila's Nest Vineyards(12pm) Newtown: Bittersweet Descent at Reverie Brewing Company(2pm - 5pm) Newtown: Red Planet (Day's In between Show) at NewSylum Brewing Co.(3pm - 6pm) ☀️🎶Norwalk: Silver Steel Band - FREE Summer Concert Series at Calf Pasture Beach (5pm – 7pm) Norwalk: Sun People Funk at 314 beergarden(3pm- 6pm) Norwalk: Billy Genuario at Washington Prime(12pm - 3pm) Piermont, NY: Piano Brunch Sunday at OTTO'S(12pm - 3pm) Pawling, NY: Holy Roller at Daryl's House Restaurant & Music Club(7pm) ☀️🎶Redding: Marc Berger at The Redding Town Green (6-8pm) Shelton: DJ PAUL0 at Pier131 Kitchen + Bar(6:30pm - 9pm) Shelton: What Up Funk at Spotted Horse Tavern(8pm) Stratford: Vibes Atlantic at Joey C's Boathouse Cantina & Grill(3pm - 7pm) Stratford: JukeBox Radio at Blackbird's Nest(5pm) ☀️🍔 Stamford: Hey Stamford Food Festival at Mill River Park(12pm –8pm) ☀️🎶Stamford: Bookends Band - Music at the Bartlett(5pm –7pm) ⭐😂🎟️Stamford: Sunday Night Comedy at New York Comedy Club Stamford(7pm) ☀️🎶Trumbull: Secret Lita at Trumbull’s Sunday Summer Concert Series at the Gazebo(4pm) Westport: Hitch Trio at Walrus Alley(5pm - 8pm)