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The 8th Annual Westoberfest Craft Beer and Family Fall Festival Returns to Downtown Westport For an Unforgettable Celebration

Get ready to raise a glass and toast the return of one of Westport’s most anticipated fall festivals. The Westoberfest Craft Beer and Family Fall Festival is back for its eighth year, bringing together craft beer enthusiasts, families, and the community for an afternoon full of flavor, music, activities, and fun.


The celebration takes place on Saturday, October 4, 2025, from 12:00 to 6:00 PM in the heart of downtown Westport at Sigrid Schulz Plaza on Elm Street.


Beer lovers will enjoy a diverse selection of local and regional brews, from crisp lagers and bold IPAs to rich stouts and refreshing cocktails, as well as non-alcoholic options. The tasting tent will be open from 1:00 to 5:00 PM, with attendees receiving a punch ticket to guide their tasting journey. Completed punch tickets may be submitted for a chance to win raffle prizes. New this year, Castle Wine & Spirits will join the tasting area as your Westoberfest sommeliers, guiding you through seasonal wines and curated pairings perfect for the fall season ahead.


The eight annual festival promises more than just fantastic brews; it will also feature children’s activities, on-site vendors, delicious food, friendly competitions, and lively music.


Children can enjoy face painting, pumpkin decorating, and flower crown making, and, new this year, families can enjoy the Westoberfest Petting Zoo hosted by Kelly’s Kids. Additionally, various vendors will be on-site for shopping pleasure, including Beyond Yoga, Filling in the Blanks, Here for You, Hughie’s Jewelry & Coins, Inclusive Brew, Joli Lily, Leaf Filter, Legacy Martial Arts, New Mom School Westport, Real + Co, Renewal by Anderson, Stifel E3 Wealth Advisory Group, and others. Looking for a bite to eat? Enjoy traditional German fare from Colossal Kielbasa, along with local favorites including Haven Hot Chicken, Paradise Island Food, COBS Bread, Sushi Jin, and refreshing lemonade from LemonNate’s.


On stage this year, Westoberfest kicks off with live music by Dan Tressler from 12:30 to 2:30 PM. His impressive versatility and infectious energy make for a true musical journey. Following Dan, One Bad Oyster returns to the stage from 2:30 to 5:30 PM. This energetic ska-surf band from Fairfield County has built a reputation for electrifying performances, blending infectious beats that get everyone moving. If you weren’t dancing last year, this year is your chance!


Returning this year, festival-goers can unleash their competitive spirit in the annual Westoberfest contests. Outlast the crowd in the stein-holding challenge or, if you’ve got an appetite, face off against fellow Westporters in the hot dog eating competition. CBS News Weather Anchor and proud Westport resident Lonnie Quinn returns as host and is ready to bring his energy to the festivities. Competitions will be held on the main stage, so get ready to compete or bring the crowd energy to cheer on your favorite participants.


Save on tickets by purchasing in advance at westportdowntown.com/westoberfest. Beer tasting participants receive an age-verified wristband (age 21+), tasting punch card, as well as a collectible Westoberfest tasting glass and koozie, sponsored by Lux Bond & Green.


Festival Admission + Beer Tasting Pass (21+)

Adult/Senior - Now: $60 | Door: $75

Festival Admission ONLY (No Beer)

Adult - Now: $20 | Door: $25

Senior - Now: $10 | Door: $15

Child: (4-12 yrs) - Now: $5 | Door: $10

Child (Under 4) - Free Admission


Westoberfest is produced by the Westport Downtown Association, in collaboration with The Grapevine and Castle Wine & Spirits. Thank you to The Grapevine for curating the craft beer and to Castle Wine & Spirits for sharing their wine expertise at this year’s festival.

Thank you to our generous corporate sponsors, Lux Bond & Green, All American Waste, Leifer Properties, Gault Family Companies, Brooks Torrey & Scott, Inc., Meadow Ridge, Fabrikant, MG Greenberg & Associates, for their support in making this event possible.


Thank you to our in-kind and media sponsors, 06880, All American Waste, Fairfield After Dark, Pure Barre Westport, Royal Flush, Videler Photography, and WSHU Public Radio for their support.


Westoberfest is a celebration of our community, with a portion of proceeds from the event going to support downtown Westport’s beautification projects and future community events.


For more information, check out www.westportdowntown.com/westoberfest for up-to-date listings of breweries, vendors, and exciting news! Westoberfest is a rain-or-shine event.


For sponsorship opportunities, please contact Huong Belpedio, Finance & Operations Director | operations@westportdowntown.com

The Westport Downtown Association, Inc. is a 501 (c)(3) charitable organization whose mission is to promote the economic interests of the business community for a vibrant and prosperous downtown Westport.

The 8th Annual Westoberfest Craft Beer and Family Fall Festival Returns to Downtown Westport For an Unforgettable Celebration

Last Chance to See The Lightfoot Band at Edmond Town Hall — Tickets Going Fast

By Cathy Ithier • October 5, 2026
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!

Nutmeg Original Music Series Launches Listening Room with Drew Ryder Smith & Melissa Capezio

By Cathy Ithier • October 2, 2026
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

The Moonrise Cartel Nominated for 2026 New England Music Awards’ Live Act of the Year

By Cathy Ithier • October 1, 2026
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!

Sip, Stroll, and Savor: The 17th Annual Downtown Milford Wine Trail Returns October 10th

October 1, 2026
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!

Stamford Downtown Parade Spectacular Returns November 22 with Giant Balloons & Holiday Fun

October 1, 2026
STAMFORD, CT — Save the date! One of Stamford’s biggest holiday traditions returns Sunday, November 22, when the 33rd Annual Stamford Downtown Parade Spectacular takes over the streets of Downtown Stamford. Beginning at 12 p.m. , the parade is expected to draw thousands of spectators for an afternoon filled with giant helium balloons, marching bands, dancers, floats, holiday characters and Santa. This year’s lineup includes 15 giant balloons , with favorites including Abby Cadabby, Clifford the Big Red Dog, Elmo, Frosty the Snowman, Jonathan the Husky, Mr. Potato Head, Oscar the Grouch, Rudolph the Red-Nosed Reindeer and The Very Hungry Caterpillar. Music will fill the streets with the University of New Haven Marching Band, NYPD Emerald Society Pipe & Drum Band, Fairfield County Pipes & Drums and several high school marching bands, along with dance and performing arts groups from throughout the region. The parade steps off at Summer Street and Hoyt Street and concludes near Atlantic and Federal Streets. The festivities begin a day early with the Point72 Giant Balloon Inflation Party on Saturday, November 21, from 3–6 p.m. at Hoyt and Summer Streets. Families can watch the massive balloons come to life while enjoying music, performers, characters and a visit from Santa. Stamford Downtown Parade Spectacular Sunday, November 22, 2026 | 12 p.m. Downtown Stamford, Connecticut

FAD’s Hot Picks for Halloween Adventures In and Around Fairfield County

By Cathy Ithier • September 30, 2026
Halloween season is creeping into Connecticut and the Hudson Valley with haunted trails, glowing pumpkins, ghostly legends, historic cemeteries and plenty of things that go bump in the night. Fairfield After Dark has rounded up some of our Hot Picks for Halloween Adventures in and around Fairfield County — from family-friendly pumpkin spectaculars to attractions made for those who really like a good scare. 👻 FAIRFIELD COUNTY Legends of Fear — Shelton One of Connecticut’s major Halloween attractions combines a Haunted Hayride with The Hallow Trail, elaborate scenes, actors and plenty of nighttime scares. Fright Haven — Stratford More than 20,000 square feet of indoor scares make Fright Haven a great choice when you want a haunted-house experience without worrying about October weather. Harvest Fair After Dark — Fairfield A local Halloween adventure featuring a haunted hayride, wooded trails and multiple nighttime attractions. A Haunting at Mill Hill — Norwalk History meets Halloween with lantern-lit encounters and chilling stories inspired by Norwalk’s past. 🎃 NEW HAVEN COUNTY Trail of Terror — Wallingford One of Connecticut’s longtime Halloween favorites sends visitors through an enormous outdoor haunted trail filled with elaborate scenes and live scares. Evidence of Evil — Middlefield Lyman Orchards gets sinister after dark with an immersive haunted attraction featuring theatrical sets, characters and plenty of surprises. Haunted Trolley — East Haven The Shore Line Trolley Museum puts a uniquely Connecticut spin on Halloween with its nighttime haunted trolley experience. 🍂 LITCHFIELD COUNTY Scarecrows in the Meadow — Litchfield | Oct. 17–Nov. 1 More than 50 creative, funny and spooky scarecrows take over the historic Tapping Reeve Meadow. Open daily from dawn to dusk and FREE to visit. This is a great choice for families looking for Halloween fun without the fright factor. 🎃🐎 FAD ROAD TRIP: SLEEPY HOLLOW COUNTRY If Halloween had a hometown, Sleepy Hollow would have a pretty strong claim to the title. For 2026, Sleepy Hollow Country has created an entire Halloween season around Washington Irving, Ichabod Crane and, of course, the legendary Headless Horseman. ⭐ FAD HOT PICK: Twilight Village at Sleepy Hollow | Oct. 2–31 Historic Philipsburg Manor transforms after dark into an immersive Halloween village filled with storytellers, fire performers, eerie encounters, a roving brass band, evening market and a dramatic encounter with the Headless Horseman . 🔎 Headless Horseman Files | Oct. 2–31 Here’s something completely different! Become part of the mystery surrounding the disappearance of Ichabod Crane. Visitors explore Philipsburg Manor, meet suspects including Katrina Van Tassel, Brom Bones and Hulda the Witch, gather clues and decide what really happened. ✨ Spirits of Sleepy Hollow Country | Oct. 2–31 Illusionists Mark Clearview and Nick Wallace bring magic and the supernatural together in another new Sleepy Hollow experience centered around the legendary Horseman. 🎃 Great Jack O’Lantern Blaze — Croton-on-Hudson | Sept. 18–Nov. 8 More than 7,000 hand-carved jack-o’-lanterns illuminate ten acres at Van Cortlandt Manor. New for 2026 is a longer trail with additional displays, movie-monster photo opportunities, storybook characters and a pumpkin dance party. This one is spooky rather than scary , making it a great choice for families. 👻 Sleepy Hollow Haunted Hayride | Oct. 17 Want your Sleepy Hollow experience a little scarier? Take a haunted hayride through the village that made the Headless Horseman famous. ⚰️ Sleepy Hollow Cemetery Explore one of America’s most famous cemeteries — and the final resting place of Washington Irving — with seasonal daytime and evening guided tours. 🏰 Lyndhurst Mansion — Tarrytown Halloween and Gothic architecture were made for each other. Lyndhurst adds seasonal Halloween programming to one of the Hudson Valley’s most dramatic historic estates. FAD TIP: There is enough happening throughout Sleepy Hollow, Tarrytown, Irvington and Croton-on-Hudson to turn this into a complete Halloween day trip — or an overnight getaway. 👻 PUTNAM COUNTY, NY Spellbound — Carmel Head into the woods for a different kind of Halloween adventure combining a haunted trail with live entertainment, fire performances and a Mystic Market atmosphere. Putnam makes an especially easy Halloween road trip from Danbury, Ridgefield and northern Fairfield County. 🎃 DUTCHESS COUNTY, NY Kevin McCurdy’s Haunted Mansion — Wappingers Falls | Oct. 2–Nov. 1 This Hudson Valley Halloween institution celebrates its 50th season in 2026 with an expanded outdoor walk-through adventure through an eerie forest, ghost town, cemetery and monster-filled environments. Haunted Beacon Ghost Walk — Beacon Grab a lantern and explore the darker side of Beacon through local ghost stories, legends, historic locations and tales of paranormal activity. Ages 16+ due to mature subject matter. Stony Kill Farm Spooktacular — Wappingers Falls A family-oriented Dutchess County Halloween tradition bringing seasonal fun to the historic farm setting. 👻🎃 FAD’S HALLOWEEN ADVICE Whether you want glowing pumpkins, a haunted hayride, an all-out haunted attraction or an entire weekend immersed in the legend of the Headless Horseman, there is no shortage of Halloween adventures within driving distance of Fairfield County. But if you're planning one Halloween road trip for 2026, Sleepy Hollow Country deserves serious consideration. Many Halloween attractions require timed tickets, and popular October weekends can sell out. Always check dates, age recommendations and ticket availability before heading out. Happy Haunting from Fairfield After Dark! 👻🎃🐎
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