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Sip Your Way Through Stamford! WineFest on Bedford Returns October 3

Stamford, CT: Wine lovers, mark your calendars! WineFest on Bedford takes over Latham Park in Stamford Downtown on Saturday, October 3, from 3–5:30 PM, bringing together wine tastings, live music, food, shopping and plenty of reasons to spend a fall afternoon downtown.

Presented by Stamford Downtown, WineFest will feature wines from more than 20 wineries and brands, giving guests the opportunity to sip and sample their way through the afternoon.


Participating wineries and brands include Big Salt, Cambria Winery, Cline Cellars, Evaton, Ex Post Facto, Gratsi Wine, Hampton Water Wine, Kendall-Jackson, La Crema Winery, Miraval, The Wine Room Stamford and more.


And it’s not just about the wine! Guests can enjoy live music and lawn games, grab a bite from food vendors including Amazing Momo, Curated Creations, Molly & Mags and Sugar Edit, and browse local vendors such as Honey Bee Flower Truck, Northeast Vinegars, Other Things Only, Plain and Fancy Boutique, Rachel Rae Epoxy, Henna by Jada and Psychic of Stamford.


🍷 Get Your Tickets — Early Bird Pricing Ends September 15!

General Admission: $30 Early Bird / $40 Advance
VIP: $40 Early Bird / $50 Advance

Early Bird pricing ends September 15 at 11:59 PM, so don't wait if WineFest is on your fall bucket list!

Admission includes a tasting glass, unlimited wine tastings while supplies last and entertainment.


Want to get the party started early? A limited number of VIP tickets include special sampling opportunities and 2 PM admission, one hour before General Admission.

🎟️ Grab Your Tickets:
https://aftontickets.com/2026stamfordwinefest


WineFest on Bedford

πŸ“ Latham Park, Bedford Street, Stamford Downtown
πŸ“… Saturday, October 3, 2026
⏰ General Admission: 3–5:30 PM | VIP Entry: 2 PM
πŸ”ž 21+ Only


Grab your friends, raise a glass and enjoy a fall Saturday in Stamford Downtown! 🍷🎢

Sip Your Way Through Stamford! WineFest on Bedford Returns October 3

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Things to Do in Fairfield County: Live Music, Comedy & Halloween Fun | Oct. 21–25

By Cathy Ithier • October 21, 2026
Fairfield County's Fall Entertainment Guide: October 21–25, 2026 Fairfield County's fall entertainment lineup just keeps getting better! From legendary musicians and laugh-out-loud comedy to Halloween-inspired performances, some of our favorite venues are bringing plenty of excitement to the stage this week. Here's what's happening October 21–25! Edmond Town Hall | Newtown It's a star-studded weekend at Edmond Town Hall! Rock & Roll Hall of Famer John Oates & The Good Road Band take the stage Friday, October 23. On Saturday, October 24, get ready for a wildly entertaining Halloween tradition with The Rocky Horror Picture Show featuring a live shadow cast. Sunday's performance of Gary Gulman's 7th Hour is already SOLD OUT! The Palace Danbury | Danbury Prepare for an afternoon of mind-blowing comedy! Peter Antoniou, The Psychic Comedian , brings his unique blend of mind reading, humor, and audience interaction to The Palace Danbury on Sunday, October 25, at 3 p.m. Aquila's Nest Vineyards | Newtown There's something happening nearly every day at Aquila's Nest Vineyards! Kick things off with Witchy Wednesday , followed by a Hocus Pocus-inspired musical drag show Thursday . Friday features Acqua Azzurra Italian Music , while Saturday brings Here's Elton, an Elton John tribute . Wrap up Sunday with free live music by Simone Dube from 2–5 p.m. and the ever popular Hocus Pocus Drag Show back again at 6:30 PM for another fabulous drag show! New York Comedy Club | Stamford Need a good laugh? New York Comedy Club Stamford delivers another fantastic weekend of stand-up! Luke Severeid kicks things off Thursday, followed by Angelo Colina with four performances across Friday and Saturday. Reserve your seats before they're gone! The Palace Theatre | Stamford Two big nights of comedy are headed to The Palace Theatre Stamford ! Catch comedian Matteo Lane on Thursday, October 22 , followed by Killers of Kill Tony on Friday, October 23, at 8 p.m . Check ticket availability and get ready for a weekend of laughs! Your Local Entertainment Starts Here! From live music and comedy to Halloween thrills, Fairfield After Dark keeps you connected to the hottest shows, events, and happenings in Fairfield County and beyond. Don't miss out! Explore our event calendars , discover what's happening in and around your town, and grab your tickets before the best shows sell out! Explore More Events at FairfieldAfterDark.com
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