Pickles, Jazz & Pasta: 10+ Must-See Festivals Lighting Up Connecticut This Weekend

Stamford Downtown is excited to announce the return of the Stamford Downtown Parade Spectacular. The holiday season will officially kick off in Stamford Downtown on November 23 with the 32nd annual Stamford Downtown Parade Spectacular . The parade is one of the largest of its kind in the country, with giant helium balloons drawing approximately 100,000 spectators annually. This parade is produced and funded by Stamford Downtown Special Services District with generous support from local property owners and businesses. Planned highlights of the parade include 15 giant balloons including favorites Bumble the Abominable Snowman, Clifford the Big Red Dog, Elmo, Mistletoe the Snowman, Mr. Potato Head, Oscar the Grouch, Peppa Pig, Rudolph the Red-Nosed Reindeer, Shrek, Super Grover, and more to be announced. In addition to the procession's signature balloons, the streets will be filled with music from the NYPD Emerald Society Pipe & Drum Band, Fairfield County Pipes & Drums and high school marching bands from Westhill, Brentwood, Uniondale and Wyandanch. New to the parade this year are the Pride of Port Chester High School Marching Band, Ballet Folklórico de las Américas (BFAmericas) and the Ballet School of Stamford. Additional fabulous groups include Center Stage Dance Studio, City Center Dance Performing Company, Dance on the DL, Locust Performing Arts Center of Stamford and The Pulse Performing Arts Studio's nova jazz., fabulous Floats, the Second Company Governor’s Horse Guard, Santa and more! Colin Cosell, Public Address Announcer for the New York Mets and New York Riptide, will return as the parade’s Master of Ceremonies. The parade is scheduled to begin at noon on Sunday, November 23 at the intersection of Summer Street and Hoyt Street and conclude on Atlantic Street and Federal Street, just a short block from the Stamford Transportation Center served by Metro-North Railroad, Amtrak, and CTtransit. On the eve of the parade, the Point72 Giant Balloon Inflation Party will be held on Saturday, November 22 from 3-6 p.m. at the intersection of Hoyt Street and Summer Street. This pre-parade event has been hosted by Stamford-based Point72 Asset Management since 2014 and allows spectators a behind-the-scenes look at the balloons as they come to life. Music, parade talent, cartoon characters, and Santa will greet and delight spectators. For more information or to see what’s happening in Stamford Downtown, please visit https://stamford-downtown.com/event/stamford-downtown-parade-spectacular/ or follow us @stamforddowntown . About Stamford Downtown Special Services District: Stamford Downtown Special Services District is responsible for creating, managing and promoting a quality environment for people, which enhances the economic vitality of Stamford Downtown. www.stamford-downtown.com

The Avon Theatre Film Center celebrated an extraordinary night of music, film, and legacy at its 2025 Lifetime Achievement Gala honoring Clive Davis, the legendary record producer and five-time GRAMMY® Award winner whose influence has shaped generations of artists. The sold-out event on October 14th featured live performances, heartfelt tributes, and a star-studded celebration of Davis’s almost six-decade music career. Highlights included: Musical performances by Ryan Shaw (“Bridge Over Troubled Water”), Mandy Gonzalez (“Don’t Cry Out Loud”), Paul Shaffer (“Piano Man”), and Capathia Jenkins (“I Will Always Love You”), with Todd Ellison serving as music director. Video tributes from Barbra Streisand, Martha Stewart, Melissa Manchester, and Stevie Wonder honored Davis’s unmatched contributions to the industry. Presentation of the award by Pat Houston, who delivered an emotional tribute recognizing Davis’s enduring mentorship and his pivotal role in shaping Whitney Houston’s career.  The evening concluded with all performers joining together for a moving rendition of “That’s What Friends Are For,” bringing the audience to its feet in celebration of friendship, artistry, and shared history. Proceeds from the gala support the Avon Theatre’s nonprofit mission to present independent, foreign, and documentary films, and to expand its educational and cultural programming in the heart of downtown Stamford. In addition to the live event, the Avon’s online auction remains open through October 28, offering exclusive items, experiences, and collectibles to benefit the theatre. Bidding details can be found here .

The Rocky Horror Picture Show returns to Edmond Town Hall this October for a weekend of outrageous fun, audience participation, and cult-classic energy! Whether you’re a seasoned “Rocky” fan or a first-timer curious about the experience, we’ve got two ways for you to join the madness. Friday Night: Movie Only Step into the world of Dr. Frank-N-Furter and company for a Movie-Only Screening of The Rocky Horror Picture Show. Bring your props (within venue guidelines), dress up if you dare, and get ready to sing, shout, and dance along to every iconic scene. 📅 Friday, October 24 🕒 Time: 7:30pm 🎟️ Tickets: edmondtownhall.org Perfect for newcomers or those who want a low-key Rocky Horror experience without the live cast. Saturday Night: Movie + Shadow Cast Performance If you want the full Rocky Horror experience, don’t miss Saturday Night’s Live Shadow Cast Performance! A talented troupe will act out the movie in front of the screen, complete with costumes, choreography, and audience interaction that brings the film to life in spectacular fashion. 📅 Saturday, October 25 🕒 Time: 7:30pm 🎟️ Tickets: edmondtownhall.org 👠 Expect plenty of energy, laughs, and a “Time Warp” you’ll never forget! Let’s Do the Time Warp Again! Don’t miss this annual tradition that brings the community together for a night of outrageous fun and cult cinema magic. Grab your friends, grab your fishnets, and get your tickets before they sell out! 👉 Tickets: edmondtownhall.org

Autumn has arrived in Fairfield County, bringing with it crisp air, colorful foliage, and a calendar packed with seasonal celebrations. From cozy harvest festivals and spooky Halloween haunts to pumpkin patches , apple orchards, and charming local markets, there’s no shortage of ways to embrace the magic of fall. Whether you’re looking to sip cider under the stars, take the kids on a hayride, get lost in a corn maze, or enjoy a night of live music and local brews, this season’s lineup has something for everyone. So, grab your favorite sweater, gather your family and friends, and explore all the fun, food, and festivities happening in and around Fairfield County this fall . Below, we’ve rounded up some of the area’s can’t-miss events, from weekend fairs to haunted happenings — and everything in between. Wednesday, October 15 📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm) Bethel: Jim Royle's Caribbean Jazz Connection LIVE at La Zingara(7pm) Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(11am-5pm) Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm) Higganum: Pumpkin Patch at Halfinger Farms(9am-6pm) Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm) 📣Newtown: Astrology Reading Night at Aquila's Nest Vineyards(5:30pm) 📣Newtown: Pilates with Goats at Aquila's Nest Vineyards(6pm) 📣Newtown: Sip n Learn French Class at Aquila's Nest Vineyards(6pm) North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm) Pawling, NY: Toronzo Cannon LIVE at the Daryl's House(7pm) 📣Stamford: Comedian Jenny Zigrino at New York Comedy Club Stamford(7pm) Tarrytown, NY: Ghost Tours of The Music Hall 2025 LIVE at Tarrytown Music Hall(8pm) Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm) Wilton: Beauty is Resistance: art as antidote(11m-6pm) Thursday, October 16 📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm) Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(11am-5pm) Bedford, NY: Hudson Valley Wind Quintet LIVE at Bedford Playhouse(7pm) Fairfield: Tangled Vine LIVE at The Sinclair(8:30pm) Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm) Higganum: Pumpkin Patch at Halfinger Farms(9am-6pm) Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm) Milford: Young Dan & Friends LIVE at Cafe Atlantique(5pm-8pm) 📣Newtown: Build Your Own Apple Bar at Aquila's Nest Vineyards(6pm) 📣Newtown: Hocus Pocus Need Wine to Focus Drag Show at Aquila's Nest Vineyards(6:30pm) 📣Newtown: Newtown Speaker Series: Wally Lamb at Edmond Town Hall(7pm-9pm) Norwalk: Live music with STEVEN KEITH!(5:30pm-8:30pm) Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm) Port Chester, NY : An Evening with Patty Griffin + Rickie Lee Jones LIVE at the The Capitol Theatre(8pm) Pawling, NY: Sir Paul: Tribute to Paul McCartney LIVE at the Daryl's House(8pm) Ridgefield: Traditional Irish Session LIVE at Nod Hill Brewery(6pm) Stamford: The Lodge at the Riverbank Ramble - Don Zlotnick & Christine Chanel (6:30-9:30pm) 📣Stamford: Comedian Usama Siddiquee - The Usama Bin Laughin Tour at New York Comedian Club Stamford(7pm) 📣Stamford: Not Dead Yet! - John Cleese and the Holy Grail at 50 at The Palace Stamford(7:30pm) South Windsor: Foster Family Farm Corn Maze(10am-6pm) Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm) Tarrytown, NY: Pink Martini All Stars LIVE at Tarrytown Music Hall(8pm) Westport: Chris Coogan Meets the Jazz Rabbi LIVE at Jazz at the Post(7:30pm-10:30pm) Wilton: Beauty is Resistance: art as antidote(11m-6pm) Friday, October 17 Bridgeport: Elana Zabari LIVE at Port 5(5pm-8:30pm) 📣Bridgeport: North County Band with Sasco Dead - Park City Music Hall - Bridegeport CT(8pm-11pm) Bethel: MICHAEL BRAM LIVE at Shakedown Street(6:30pm) Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(11am-5pm) 📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm) Danbury: Shameless LIVE at Elicit Brewing Danbury(9pm) Danbury: DJ GIODE at the Speak Easy - Elicit Brewing Danbury(10pm) Fairfield: DJ CHARLIE at the Speak Easy - Elicit Brewing Fairfield(10pm) Fairfield: Harvest Fair Halloween Haunt(7pm-10pm) Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm) Hartford: The Name Droppers Perform Live At Black-Eyed Sally's Southern Kitchen And Bar(8am-11pm) Higganum: Pumpkin Patch at Halfinger Farms(9am-6pm) Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm) Milford: Paul Loether LIVE at Cafe Atlantique(6:30pm-9:30pm) Mamaroneck, NY: Naturally 7 LIVE at Emelin Theatre(8pm) New Milford: The Winnie Shins LIVE at Housatonic Brewery(7pm-10pm) New Haven: Ghosts of New Haven(7:30pm) 📣Newtown: Frank Lind LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) 📣Newtown: Local Cheese & Wine Pairing at Aquila's Nest Vineyards(6pm) 📣 Brie & Vino Nights at Aquila's Nest Vineyards(6:30pm) Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm) Newtown: Sal Grillo LIVE at Perfusion Bar(8pm-11pm) 📣Norwalk: Brother Dave LIVE at SONO 1420(6pm-9pm) Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) Norwalk: Fake ID Band LIVE at 314 Beer Garden(7pm-11pm) North Salem, NY: Mystic Moon at Harvest Moon Farm and Orchards(7pm) North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm) Pawling, NY: The Third Mind LIVE at the Daryl's House(8pm) Ridgefield: Old Bob LIVE at Nod Hill Brewery(6pm) Ridgefield: The Loner ~ The Music of Neil Young LIVE at Nod Hill Brewery(6:30pm) Rowayton: The Third Rail LIVE at Sails American Grill(9:30pm) Rye, NY: Scarded By The Sound at Playland(8pm-11pm) Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm) Stratford: Jon Hollywood LIVE at Windmill Tavern(5pm) Stamford: Whiskey & Woodfire at Stamford Museum & Nature Center(6:30pm) 📣Stamford: Comedian Brittany Brave at New York Comedy Club Stamford(7pm) Stamford: Dive Bar Confessional LIVE at Third Place by Half Full Brewery(7pm-9pm) Stamford: Suck R' Punch LIVE at Bobby V's(7pm-10pm) 📣Stamford: Anthony Rodia: Laugh till It Hurts Tour at The Palace Stamford(8pm) Stamford: Something Fried LIVE at Tiernan's Bar(9:30pm) 📣Stamford: That's Fair Comedy at New York Comedy Club Stamford(9:30pm) Stamford: Club Shebeen at Tigin Irish Pub(10pm) Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm) Tarrytown, NY : Marty Stuart and His Fabulous Superlatives LIVE at Tarrytown Music Hall(8pm) Wethersfield: Cove Side Carnival 2025(5pm-10pm) 📣Westport: StoryFest to Celebrate Storytelling in All Its Forms with Special Film Screening and Concert Event(6:30pm) Westport: Ruff Dogs LIVE at Black Duck Cafe(9:30pm) Saturday,October 18 📣Bridgeport: The Anna & Raven Goodwill Trick or Treat Day at Sacred Heart University's Discovery Science Center and Planetarium(10am) Bridgeport: Oktoberfest 2025 at Foolproof Brewing Co. Bridgeport(12pm-10pm) Bethel: JUSTIN VIRGA LIVE at Shakedown Street(6:30pm) Bethel: Beatnicks LIVE at Notch 8(8pm) 📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm) Bedford, NY: Alison Shearer Album Release Concert and Party LIVE at Bedford Playhouse(8pm) Branford: The Traveling Bazaar at Caius Brewing(11am-5pm) Colchester: Colchester Food Truck and Wine Festival(11am-6pm) Danbury: Tony & The West Siders LIVE at Charter Oak Taproom(4pm-7pm) Danbury: Five Dollar Shake LIVE at Elicit Brewing Danbury(9pm) Danbury: DJ MIKEY LIVE in the Speak Easy at Elicit Brewing Danbury(10pm) Easton: Pumpkin Patch at Silverman's Farm(9am-5pm) East Windsor: Pumpkin Patch at Connecticut Trolley Museum(10am-4pm) Fairfield: Fairfield Harvest Market(10am-4pm) Fairfield: Juicebox LIVE at Elicit Brewing Fairfield(9pm) Fairfield: DJ JAY SPRING LIVE in the Speakeasy at Elicit Brewing Fairfield(10pm) Fairfield: Harvest Fair Halloween Haunt(7pm-10pm) Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm) Goshen: Fall Festival on the Zoo Farm - Action Wildlife Foundation(5pm) Harwinton: All Hallows Weekend at The Connecticut Renaissance Faire(10:30am-6pm) Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm) Litchfield: Bunnell Farm Corn Maze & Pumpkin Patch(10am-5pm) Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm) Milford: Milford Artisan Market(10am-4pm) Mystic: Mystic Apple Festival(11am-6pm) New Canaan: STRICTLY BUSINESS LIVE at Gates Restaurants & Bar(8:30pm-11:30pm) New Milford: Dan's Garage LIVE at Housatonic Brewery(7pm-10pm) New Milford: Scarrybrooke Park CT's Haunted Trail(6pm) New London: Boo Bash at the Beach 5!!!(11am-4pm) New Haven: Ghosts of New Haven(7:30pm) 📣Newtown: Long River Jam LIVE at Aquila's Nest Vineyards(2:30pm-5:30pm) 📣Newtown: Silent Disco Costumes Party at Aquila's Nest Vineyards(6pm) Newtown: Chris Daly LIVE at Newsylum Brewing(3pm-6pm) Newtown: Night Corn Maze at Castle Hill Farm(5pm-8pm) 📣Newtown: Mike DelGuidice comes to Edmond Town Hall(8pm-10pm) Newtown: DJ D Brown LIVE at Perfusion Bar(8pm-11pm) Newtown: Fall Festival at Castle Hill Farm(10am-5pm) Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) Norwalk: Music of the Sea: Norwalk Concert Hall at Norwalk City Hall(7:30pm-9pm) North Salem, NY: Mystic Moon at Harvest Moon Farm and Orchards(7pm) Old Greenwich: Phunk and Roses LIVE at Bosco's Bar & Grill(9pm-12am) Putnam: Putnam's Great Pumpkin Festival(10am-3pm) Pawling, NY: Jim Pospisil LIVE at the Daryl's House(12pm-2pm) Pawling, NY: WILDSIDE LIVE at the Daryl's House(8pm) Ridgefield: Skylab LIVE at Nod Hill Brewery(3:30pm) Redding: Not My Problem LIVE at Milestone(9pm-12am) Shelton: Juliet’s Run LIVE at Pier 131(9:30pm-12am) Shelton: Legends of Fear(7pm) 📣Stamford: WineFest on Bedford(3pm-5:30pm) 📣Stamford: Comedian Natalie Cuomo at New York Comedy Club Stamford(7pm-9:30pm) Stamford: Slowburn LIVE at Tiernan's Bar(9:30pm) Stamford: Blood-Manor(6pm-10pm) Stratford: Whabendos LIVE at Windmill Tavern(8pm) Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm) Tarrytown, NY: Eric D'Alessandro LIVE at Tarrytown Music Hall(6 & 9pm) Wethersfield: Cove Side Carnival 2025(12pm-10pm) Westport: Beardsley Gala(6pm) Westport: Bad Manners LIVE at Black Duck Cafe(9:30pm) Wilton: Halloween Spooktacular at The Riverbrook Regional YMCA(4pm-7:30pm) Windsor: Pumpkin Patches, Hay Rides and Mazes / Corn at Brown's Harvest(10am-5pm) Sunday, October 19 Bethel: TYE DYE BRUNCH w/ ROB GLASSMAN LIVE at Shakedown Street(12pm) Bethel: Black Rock Blues LIVE at Notch 8(4pm) Colchester: Colchester Food Truck and Wine Festival(11am-6pm) Danbury: Comedian Brad Upton at The Palace Danbury Theatre(2pm) Darien: Orchestra Lumos: Small Space Series- A Tale of Two Prodigies(3pm-4:30pm) Easton: Pumpkin Patch at Silverman's Farm(9am-5pm) East Windsor: Pumpkin Patch at Connecticut Trolley Museum(10am-4pm) Guilford: Making Chocolate the 18th Century Way at Henry Whitfield State Museum(10am-4pm) Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm) Harwinton: All Hallows Weekend at The Connecticut Renaissance Faire(10:30am-6pm) Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm) Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm) Mystic: Mystic Apple Festival(11am-6pm) Milford: Milford Artisan Market(10am-4pm) Mamaroneck, NY : Fearless – The Taylor Swift Experience LIVE at Emelin Theatre(2pm) New Haven: Ghosts of New Haven(7:30pm) 📣Newtown: Mini Cheesecakes & Sweet Wines Pairing at Aquila's Nest Vineyards(12pm) 📣Newtown: A&R Duo LIVE at Aquila's Nest Vineyards(2pm-5pm) 📣Newtown: Bon Jovi Tribute Show at Aquila's Nest Vineyards(6pm) Newtown: Jailhouse LIVE at Reverie Brewing(3pm-6pm) 📣Newtown: Fine Cigars Night at Aquila's Nest Vineyards(6pm) Norwalk: Blue Skies On Mars LIVE at 314 Beer Garden(3pm-6pm) Norwalk: Jazz Band LIVE at Odeen’s Norwalk(7:15pm) Pawling, NY: Greg Raposo LIVE at the Daryl's House(12pm) Pawling, NY: Night of Nicks: The Stories, The Music of Stevie Nicks & Fleetwood Mac LIVE at the Daryl's House(7pm) 📣Stamford: Air Supply returns The Palace Stamford(7pm) 📣Stamford: Comedian Tom Shillue at New York Comedy Club Stamford(7pm) Vernon: Strong Family Farm Harvest Festival(10am-3pm) Wethersfield: Cove Side Carnival 2025(12pm-6pm) Westport: MoCA\CT Presents: Caity Gyorgy + Band(4pm-6pm) Windsor: Pumpkin Patches, Hay Rides and Mazes / Corn at Brown's Harvest(10am-5pm)

Looking for the perfect way to kick off your weekend? Head to SONO 1420 this Friday, October 17 , for another evening of live local music and craft cocktails at the Acoustic SoNo Music Series — featuring special guest Brother Dave ! Known for his soulful blend of blues, rock, and roots , Brother Dave brings a rich, expressive sound that’s perfect for SONO 1420’s cozy distillery setting. Whether it’s heartfelt originals or creative acoustic takes on crowd favorites, his performances are full of energy and musicality. Expect warm vocals, tasty guitar licks, and good vibes all night long. SONO 1420 America’s Maritime Distillery , pairs live music with their signature cocktails and craft spirits. Each week’s Acoustic SoNo performance creates a relaxed, intimate vibe — perfect for unwinding after a long week. Hungry? Grab a bite from LobsterCraft , serving up award-winning lobster rolls, burgers, and more right outside. Event Details Where: SONO 1420, 19 Day Street, South Norwalk, CT When: Friday, October 17 | 6:00 PM – 9:00 PM Admission: Free entry | Food & drinks available for purchase Come early, grab a cocktail, and enjoy great local music in one of Norwalk’s most unique venues. Brother Dave — Friday October 17 at SONO 1420!