September 14–20, 2026 Fall entertainment is kicking into high gear, and Fairfield After Dark has your week covered! From comedy and live music to vineyard happenings, a legendary cultural commentator and artisan shopping, there are plenty of reasons to get out this week. Here are FAD’s Top Picks for September 14–20! 🍷 TUESDAY, SEPTEMBER 15 | AQUILA’S NEST VINEYARDS — NEWTOWN Kick off the week at Aquila’s Nest Vineyards with Whispers From Heaven with Patricia Griffin . Enjoy the vineyard setting while checking out one of the many special experiences happening throughout the week. 👉 GET THE DETAILS & PLAN YOUR VISIT HERE 😂 WEDNESDAY, SEPTEMBER 16 | NEW YORK COMEDY CLUB — STAMFORD Need a midweek laugh? Mike Cannon hits the stage at New York Comedy Club Stamford Wednesday at 7 PM . 👉 GRAB YOUR TICKETS HERE 🍷 WEDNESDAY, SEPTEMBER 16 | AQUILA’S NEST VINEYARDS — NEWTOWN Put on those boots and head to Newtown! Country Line Dancing is on the schedule Wednesday at Aquila’s Nest Vineyards. 👉 GET THE DETAILS HERE 🎹 THURSDAY, SEPTEMBER 17 | THE BILLY JOEL LEGACY — THE PALACE STAMFORD The music of the Piano Man comes alive when The Billy Joel Legacy: A Tribute Experience takes the stage at The Palace Stamford Thursday at 7:30 PM . Billy Joel fans, this one's for you! 👉 GRAB YOUR TICKETS HERE 🍷 THURSDAY, SEPTEMBER 17 | AQUILA’S NEST VINEYARDS — NEWTOWN Aquila’s Nest keeps the week going with several Thursday experiences, including Pilates, Plant Bingo and special workshops . 👉 GET THE DETAILS HERE 🎤 FRIDAY, SEPTEMBER 18 | FRAN LEBOWITZ — EDMOND TOWN HALL, NEWTOWN Known for her razor-sharp wit, unapologetic opinions and hilarious observations on modern life, Fran Lebowitz comes to Edmond Town Hall Friday at 8 PM . Doors open at 7 PM. 👉 GRAB YOUR TICKETS HERE 🎤 FRIDAY, SEPTEMBER 18 | SIMPLY THE BEST — THE PALACE STAMFORD Get ready for the music of Tina Turner! Simply The Best: A Tribute to the Music of Tina Turner takes over The Palace Stamford Friday at 8 PM . 👉 GRAB YOUR TICKETS HERE 😂 FRIDAY, SEPTEMBER 18 | CAITLIN PELUFFO — NEW YORK COMEDY CLUB STAMFORD Start your weekend laughing with Caitlin Peluffo , performing two shows Friday night at 7 PM and 9:30 PM . 👉 GRAB YOUR TICKETS HERE 🦙🍷 FRIDAY, SEPTEMBER 18 | AQUILA’S NEST VINEYARDS — NEWTOWN Friday brings even more fun to Aquila’s Nest with Llamas & Llibations and Cruise Night . 👉 GET THE DETAILS HERE 🛍️ SATURDAY, SEPTEMBER 19 | POP SHOP MARKET — DARIEN COMMONS Shop small and discover something different when PopShop Market returns to Darien Commons Saturday from 11 AM–5 PM . Explore a curated collection of independent makers and small businesses offering apparel, jewelry, home décor, self-care products, gifts and plenty of one-of-a-kind finds. 👉 GET ALL THE DETAILS HERE 😂 SATURDAY, SEPTEMBER 19 | NEW YORK COMEDY CLUB — STAMFORD Saturday starts early with Early Bird Comedy at 4:30 PM , followed by another performance from Caitlin Peluffo at 7 PM . 👉 GRAB YOUR TICKETS HERE 🍷🎸 SATURDAY, SEPTEMBER 19 | THE 80s ROCK EXPERIENCE — AQUILA’S NEST VINEYARDS Turn back the clock at Aquila’s Nest with The 80s Rock Experience Tribute Show , happening Saturday from 6–9 PM . 👉 GRAB YOUR TICKETS & GET THE DETAILS HERE 🎹 SATURDAY, SEPTEMBER 19 | THE MIGHTY FRANKLIN BROTHERS — THE PALACE DANBURY Steely Dan fans, this one's for you! The Mighty Franklin Brothers take over The Palace Danbury Saturday at 7:30 PM . Led by brothers Jay and Carl Franklin and backed by a powerhouse lineup of musicians and horns, the band brings the sophisticated arrangements, soulful vocals and unmistakable sound of Steely Dan to the stage. 👉 GRAB YOUR TICKETS HERE 🎬🎶 SATURDAY, SEPTEMBER 19 | LABYRINTH IN CONCERT — THE PALACE STAMFORD Celebrate 40 years of a cult classic with Jim Henson’s Labyrinth: In Concert — 40th Anniversary at The Palace Stamford Saturday at 7:30 PM. 👉 GRAB YOUR TICKETS HERE 🎶 SUNDAY, SEPTEMBER 20 | GREEN EYED LADY — ODEEN’S OAK HILLS, NORWALK Wrap up the weekend with dinner and live music! Green Eyed Lady performs at Odeen’s Oak Hills Sunday from 4–7 PM . 👉 Make a Reservation here! ⭐ GET OUT & HAVE SOME FUN! From Newtown to Danbury, Stamford, Darien, Ridgefield and Norwalk , there’s plenty happening this week. These are just a few of FAD’s Top Picks — grab your tickets, make those reservations and start planning your week early! 🎶 😂 🍷 🛍️ 🎭 Get Out. Have Fun. Live Local. See even more concerts, comedy, festivals, fairs, fall happenings and Things To Do in and around Fairfield County at FairfieldAfterDark.com.

Milford, CT: Downtown Milford will come alive with the sounds of jazz on Saturday, October 3, 2026 , as the Milford Arts Council presents the inaugural Jazz’n Downtown , a new immersive celebration combining live music, local art, dining and the charm of one of Connecticut’s favorite shoreline downtowns. Presented with lead Presenting Sponsor Coastal Bridge Advisors , Jazz’n Downtown is designed to be explored at your own pace. Visitors can arrive by train, car, boat, bike or foot and spend the day strolling Milford’s historic neighborhoods, waterways, boutiques, restaurants and artisan displays — all while live jazz provides the soundtrack. Jazz Throughout Downtown Milford Award-winning jazz performers will take the stage at three outdoor venues , including locations along Milford’s scenic waterfront. The music continues throughout the downtown experience, with solo and duo jazz performers appearing at participating restaurants during brunch, lunch and dinner. It’s more than a traditional music festival. Jazz’n Downtown brings music, art, food and community together throughout the heart of Milford, allowing guests to create their own experience and discover something new around every corner. An Evening Celebrating Ella & Louis The celebration continues that evening at Parsons Veterans’ Memorial Hall with a special tribute concert honoring two of jazz music’s most legendary performers, Ella Fitzgerald and Louis Armstrong . The evening concert requires a separate ticket, while VIP packages offer an enhanced Jazz’n Downtown experience with reserved seating areas, an early reservation window for brunch, lunch and dinner, parking and reserved seating for the evening concert. About the Milford Arts Council Founded in 1972, the Milford Arts Council (MAC) is a nonprofit organization dedicated to connecting and enriching the community through music, theater, visual arts, dance, film and creative expression. MAC presents more than 200 events annually and operates from the beautifully restored historic eastbound Milford train station, as well as the Firehouse Gallery at Walnut Beach. Jazz’n Downtown 📅 Saturday, October 3, 2026 📍 Downtown Milford, Connecticut 🎷 Event Information: jazzndowntown.org 🎟️ Tickets: Eventbrite – Jazz’n Downtown: The Ultimate Jazz & Arts Experience 🎨 Milford Arts Council: milfordarts.org ☎️ Information: 203-878-6647 Come for the jazz, explore downtown Milford, discover local artists, enjoy great food and make a full day — and night — of this brand-new Connecticut arts experience.