Things to Do in Fairfield County: October 13–18, 2026 — Live Music, Comedy, Fall Festivals & Halloween Fun!

Discover fall festivals, Halloween events, haunted attractions and spooky adventures in Fairfield County and beyond with Fairfield After Dark's October Hot List!

NEWTOWN, CT: The timeless music of Gordon Lightfoot comes to Newtown this Thursday, October 8, when The Lightfoot Band takes the stage at Edmond Town Hall for an unforgettable evening celebrating one of Canada’s most legendary singer-songwriters. Featuring musicians who performed alongside Gordon Lightfoot for decades, The Lightfoot Band carries his extraordinary catalog forward with the authenticity and musicianship fans know and love. Audiences can look forward to hearing classics including “If You Could Read My Mind,” “Sundown,” “Carefree Highway,” “The Wreck of the Edmund Fitzgerald” and more. Tickets are selling fast, and only a limited number remain for Thursday night’s performance. If you’ve been thinking about going, now is the time to grab your seats. Don’t wait until show day and risk missing your chance to experience the songs of Gordon Lightfoot performed live inside historic Edmond Town Hall. Event Details Thursday, October 8, 2026 Edmond Town Hall 45 Main Street, Newtown, CT 🎟️ Limited tickets remain — purchase your tickets soon before they’re gone!

WESTPORT, CT: The Nutmeg Original Music Series , created by local singer-songwriters Bill Dempsey and Erik Moses , kicks off its inaugural Nutmeg Listening Room on Friday, October 9, 2026 , featuring Nashville singer-songwriter Drew Ryder Smith and Redding native Melissa Capezio at the Westport VFW, 465 Riverside Ave. The intimate evening will put the spotlight on original music, storytelling, and the inspiration behind the songs. “We want to offer a platform for these artists to connect with an audience over a full set of their music and introduce audiences to artists they otherwise might not know,” Dempsey explained the mission behind Nutmeg. Award-winning professional songwriter Drew Ryder Smith has shared the stage with Merle Haggard, Don Williams, Big & Rich, Lee Brice and Lady A . He notes opening for Haggard at Nashville’s legendary Ryman Auditorium with just his acoustic guitar and a stool as a career highlight. Smith has also written alongside acclaimed Nashville songwriters including Don Schlitz, Rob Snyder, Driver Williams and Bobby Pinson . Joining Smith is Melissa Capezio , a Redding native raised on traditional bluegrass and classic rock. Capezio began writing music at 16 and has since recorded two full-length studio albums. The October 9 show marks the inaugural Nutmeg Listening Room, expanding a series Dempsey and Moses created to foster community around the original music being created by Connecticut songwriters. EVENT INFORMATION Nutmeg Listening Room featuring Drew Ryder Smith & Melissa Capezio Date: Friday, October 9, 2026 Location: Westport VFW, 465 Riverside Ave., Westport, CT Tickets: $15 in advance (plus fees) | $20 at the door 🎟️ PURCHASE TICKETS

FAIRFIELD, CT — The Moonrise Cartel has been on a steady climb — and their fans have been right there with them every step of the way. Last year, the Connecticut folk-rock band celebrated a major milestone when the New England Music Awards named The Moonrise Cartel its 2025 Rising Star: Connecticut winner . Now, just one year later, the band has earned another major recognition: a 2026 nomination for Live Act of the Year. It's a fitting nomination for a band whose reputation has been built where it matters most — on the stage and in front of its fans. The Moonrise Cartel's following has steadily grown alongside the band. Their fans — affectionately known as “Cartel Members” — aren't simply listening from afar. They're showing up. The band has sold out StageOne at Fairfield Theatre Company twice, sold out Park City Music Hall and recently performed for a crowd of more than 600 at Black Rock PorchFest. Those crowds have followed The Moonrise Cartel from venue to venue, helping turn a Connecticut band with a distinctive “Folk Rock from Black Rock” sound into one of the region's increasingly recognized live acts. And now, they're taking another big step. Next Stop: The Warehouse at FTC On Saturday, October 10 , The Moonrise Cartel returns to Fairfield Theatre Company — this time to headline The Warehouse for the first time . The larger room represents another milestone in the band's progression at FTC. After twice selling out StageOne, The Moonrise Cartel is moving into The Warehouse with the same community of fans that has helped fuel its rise. Dr. B and The Remedy will open the evening, with doors at 7 PM and the show beginning at 8 PM. For longtime Cartel Members, October 10 is another opportunity to come together and celebrate how far this band has come. And if you haven't experienced The Moonrise Cartel live yet, their first Warehouse headlining show is a pretty good time to find out why they're now nominated for Live Act of the Year. Connecticut — Let's Show Them Some Love! Voting is currently open for the 2026 New England Music Awards , with The Moonrise Cartel officially among this year's nominees for Live Act of the Year. Public voting runs through October 9 , with the winners announced November 15. Let's show The Moonrise Cartel some Connecticut love and cast a vote for LIVE ACT OF THE YEAR! VOTE FOR THE MOONRISE CARTEL Then, there's only one question left: Who's meeting us at The Warehouse on October 10? The Moonrise Cartel with Dr. B and The Remedy Saturday, October 10, 2026 Doors: 7 PM | Show: 8 PM The Warehouse at Fairfield Theatre Company 70 Sanford Street, Fairfield, CT From 2025 Rising Star: Connecticut to 2026 Live Act of the Year nominee , The Moonrise Cartel's star continues to rise — and their fans continue to rise right along with them. Grab your tickets. Join The Cartel. We'll see you at The Warehouse!

Milford, CT: Get ready to raise your glass—, the Downtown Milford Business Association is hosting its 17th Annual Wine Trail on Saturday, October 10th, from 5 p.m. to 9 p.m. Say farewell to summer with a foodie-friendly evening stroll through Downtown Milford, all while supporting a great local cause. This year’s event benefits the Junior Major League of Milford, with proceeds from every ticket helping to support youth sports programs in the community. Guests will explore Downtown Milford’s charming boutiques and businesses, each serving a featured wine—provided by Marginetti Distributors—paired with delicious tastings from Milford’s favorite restaurants and eateries. Each attendee will receive a commemorative wine glass and a map of Wine Trail stops, the perfect guide for an evening of flavor, fun, and local discovery. The Downtown Milford Business Association is thrilled to continue this beloved tradition and share a night filled with community spirit, local flavor, and fall festivity. Get your tickets today and be part of this memorable evening in the heart of Downtown Milford!