From Wine Tastings to Jerry Seinfeld: Your Guide to This Weekend's Events

Get ready for a spectacular weekend in Fairfield County! From Wednesday, August 6 through Saturday, August 9, the region is buzzing with art fairs, live music, comedy shows, food truck festivals, outdoor film nights, vineyard tastings, and more. Whether you're in Greenwich, Newtown, Bridgeport, Bethel, or beyond, you’ll find something for every mood—from tribute concerts under the stars and laughter with top comedians, to wine pairings (yes, cookies included) and family-friendly open-air movies on the beach. It’s four days packed with charm, culture, and community—perfect for planning a fun-filled escape any time you’ve got a free moment.

Wednesday, August 6 

🎹 Piano Man Meets Rocket Man (Greenwich, 7pm) 
Billy Joel vs. Elton John tribute showdown in scenic Roger Sherman Baldwin Park. 
  🧘 Yoga & Music Night at Aquila’s Nest (Newtown, 6:30pm) 
Stretch, sip, and sway to live music with vineyard views. 
  ♟️ Open Play Chess in the Park (Stamford, 12pm–2pm) 
Bring a board or grab a partner—casual chess in a laid-back setting. 

•  🐯 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• 🎲 Bridgeport: Ladies Game Day at Port 5 Naval Vets(1pm-3pm) 
• Bethel: Pangea World Beat LIVE at LaZingara(7pm) 
• Fairfield: Mixtape Match LIVE at Elicit Brewing(7pm) 
• Greenwich: Piano Man Meets Rocket Man at Roger Sherman Baldwin Park(7pm) 
• 🎶 Newtown: City Express Entertainment Music Night at Aquila's Nest Vineyards(6:30pm) 
• 🎶 Newtown: Funk, R&B, Rock, 60s through 80s Night at Aquila's Nest Vineyards(6:30pm) 
• Newtown: Yoga in the Vineyard at Aquila's Nest Vineyards(6:30pm) 
• 🎨 Newbury, NH: Annual Craftsmen’s Fair at Mount Sunapee Resort in Newbury, NH(8:30am) 
• New Canaan: DREAMIN’ at Waveny Park (7:30-9:30pm) 
• Norwalk: Captain Jack Tribute Band at Calf Pasture Beach (7:00 pm) 
• ♟ Stamford: Open Play Chess in Veterans Memorial Park – Stamford(12pm-2pm) 
• 🎤Stamford: Comedians Adam Muller, Ryan Thomas, Molly Densmore, Danny DelColle at New York Comedy Club Stamford(7pm) 
• Shelton: Orchard Hill Band at Music Under the Stars Summer Concert Series(7pm) 
• Westport: Danny Weinkauf & His Red Pants Band :: Children’s Series LIVE at Levitt Pavilion(7pm) 



🍷 Thursday, August 7 

• 🍣 The Sushi Class at Aquila’s Nest Vineyards (Newtown, 6pm) 
  Learn to roll your own sushi while sipping estate wine. 
  🎬 Sand Jam Movie Night: Despicable Me 4 (Jennings Beach, Fairfield, 8:45pm) 
  A fun, free family flick with an ocean breeze and beach chairs. 
  🎤 Leann Rimes LIVE (Ridgefield Playhouse, 8pm) 
  Chart-topping country pop star performs in an intimate local venue. 
•  🐯 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Cos Cob, CT: Michelle Pauker at Music on the Great Lawn(6:30pm-8pm) 
• Danbury: SwingSet LIVE at Charter Oak Brewing(3pm-5pm) 
• Darien: Unlocking Beethoven: Part Three with Gabriel Schaff, Orchestra Lumos(7pm-8pm) 
• Fairfield: The Mertz’s at Sherman Green Gazebo(6:30-8pm)   
• 🎥 Fairfield: Sand Jam Movie Night at Jennings Beach featuring Despicable Me 4(8:45 PM) 
• 🎶 Fairfield: ETA Music LIVE at The Sinclair(8:30pm) 
• 🚘 Fairfield: CT Seaport Car Club's Car Cruise at Elicit Brewing(5pm) 
• 🎶 Fairfield: Eric Johanson LIVE at StageOne FTC(8pm) 
• Greenwich: Michelle Pauker at Music on the Great Lawn(6:30 pm–8:00 pm) 
• 🎶 Goshen: Podunk Bluegrass Music Festiva(11am) 
• Milford: DUELING PIANOS W/ THE FLYING IVORIES LIVE at Stonebridge Restaurant(6pm) 
• New Fairfield: The Chase at New Fairfield Summer Concert Series(6-8pm) 
• 🎨 Newbury, NH: Annual Craftsmen’s Fair at Mount Sunapee Resort in Newbury, NH(8:30am) 
• 🍣 Newtown: The Sushi Class at Aquila's Nest Vineyards(6pm) 
• 🎶 Newtown: Robby Schwartz LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) 
• Old Greenwich: Kayla Rae LIVE at Bosco's Bar and Grill(8pm-10pm) 
• 🎷 Piermont, NY: Live Jazz with Pianist: Adam Birnbaum & Saxophonist: Gary Smulyan(6pm-9pm) 
• Ridgefield: Live Music with the Peterman Project at 850 Degree(5pm) 
• Ridgefield: Traditional Irish Session LIVE at Nod Hill Brewery(6pm) 
• Ridgefield: Leann Rimes at Ridgefield Playhouse(8pm) 
• Rowayton: ARILDO D’SOUZA LIVE at Sails Bar & Grill(6pm-9pm) 
• 🕺 Stratford: RLP Rahsaan Langley Project LIVE at Joey C’s Boathouse(6pm-9pm) 
• 🎶 Stratford: Sheffield Drive LIVE at Blackbird's Nest(6pm-9pm) 
• 🎤 Stamford: Comedians Jill Weiner, Max Moacanin, Talal Alyan, Paige Smith-Hogan at New York Comedy Club Stamford(7pm) 
• 🏛 Weston: Summer Thursdays at Weston History & Culture Center(1pm-4pm) 
• 🎷Westport: Melissa Newman LIVE at Jazz at the Post(7:30pm-10pm) 
• 🎸 Westport: Borboletta : A Tribute to Santana LIVE at Levitt Pavilion(7:30pm) 
• 🎶 Woodbury: Matthew Dylan LIVE at Woodbury Brewing Company(8:30pm) 
• 🥁 Woodbury: Rose Hill Revival LIVE at Woodbury Brewing Company(8:30pm) 

 
🎤 Friday, August 8 

• 🎶 GOO GOO DOLLS + Dashboard Confessional (Hartford HealthCare Amphitheater, Bridgeport, 7:30pm) 
  Major alt-rock throwback under the stars—don't miss this one. 
  🍷 Girl Scout Cookies & Wine Pairing (Aquila’s Nest Vineyards, Newtown, 6pm) 
  Yes, you read that right. Cookies. Wine. Perfection. 
  🎡 Bethel Food Truck Fridays (5pm–8pm) 
  Local bites, sweet treats, and live music make this a go-to Friday hang. 
•  Bridgeport: Andy & Scott at Port 5 (5-8:30pm) 
• 🐯 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Bridgeport: GOO GOO DOLLS W/ DASHBOARD CONFESSIONAL(7:30pm) 
• Brookfield: Owl's Nest at Brookfield's Concerts in the Park(6:30 PM) 
• 🚚 Bethel: Bethel Food Truck Fridays(5pm-8pm) 
• Bethel: Don Lowe Live at Shakedown Street Eats(6:30pm) 
• Bethel: Beatnicks Band Live at Notch 8(8pm) 
• Danbury: Sugar House Band at Danbury's Summer Concert Series(7pm - 9:30pm) 
• Danbury: Vinyl Cut LIVE at Sugar Hollow(8:30pm) 
• Fairfield: Mama Train Band at Jazz Fridays(6:30 PM – 8:00 PM) 
• 🎻 Goshen: Podunk Bluegrass Music Festival(11am) 
• Mahopac, NY: AC/DC Tribute LIVE at Putnam County Golf Course(6:30pm) 
• Milford: IAN BIGGS LIVE at Stonebridge Restaurant(5:30pm) 
• New Milford: Tangled Vine LIVE at Housatonic River Brewing(7pm-11pm) 
• 🎨 Newbury, NH: Annual Craftsmen’s Fair at Mount Sunapee Resort in Newbury, NH(8:30am) 
• 🎥 Newtown: A Minecraft Movie (PG) at Edmond Town Hall(1pm-7:30pm) 
• 🦙 Newtown: Llamas and Llibations at Aquila's Nest Vineyards(5:30pm) 
• Newtown: Brie Blossom Foodie Night at Aquila's Nest Vineyards(6pm) 
• 🍪 Newtown: Girl Scout Cookies & Wine Pairing at Aquila's Nest Vineyards(6pm) 
• Newtown: MENTAL HEALTH Duo LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) 
• Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm) 
• Newtown: The Resounders LIVE at Perfusion(8pm-11pm) 
• 🎥 Newtown: ETH DRIVE-IN: The Big Lebowski (R)(9pm) 
• Norwalk: Zully Ramos and the O.G.’s LIVE at 314 Beer Garden(7:30pm-10:30pm) 
• Norwalk: Live Music With Geoff Hartwell!(10pm) 
• Ridgefield: Live Music with the Munson Haas Duo at 850 Degree(5pm) 
• Ridgefield: Faster Things - Allman Brothers Tribute LIVE at Nod Hill Brewery(6:30pm) 
• Rowayton, CT: The Bar Car Band LIVE at Sails Bar & Grill(9:30pm-12am) 
• 😂 Stamford: Kevin Nealon at New York Comedy Club Stamford(7:00pm-9:30pm) 
• Stamford: Live Music at Third Place: Homemade(7pm-9pm) 
• Stamford: Degens Band LIVE at Tiernan's Bar(10pm) 
• Shelton: Monica Rizzio at Jones Winery(2–4pm) 
• Stratford: Mike LoQuidice LIVE at Outriggers(5:30pm-8:30pm) 
• Stratford: Live Music with Sneaky Pete at Windmill Tavern(8pm) 
• Stratford: Locomotion LIVE at Joey C’s Boathouse(9pm-12pm) 
• 🎶 Westport: Moss at Music on Church Lane( 6:00pm – 9:00pm) 
• 💃 Westport: Lulada Club : NYC’s All Women Salsa Orchestra LIVE at Levitt Pavilion(7pm) 
• 🎡 Wolcott: Wolcott Country Fair(5pm-11pm) 

🎭 Saturday, August 9 

🎙 Jerry Seinfeld LIVE (Bridgeport, 8pm) 
Comedy royalty hits the stage—smart, sharp, legendary. 
  🎨 Mystic Outdoor Art Festival (Mystic, 11am–5pm) 
A perfect day trip filled with coastal charm and fine art. 
🎤  Sinatra & Dino Rat Pack Tribute (Aquila’s Nest Vineyards, Newtown, 6–9pm) 
Smooth crooners, vintage style, and wine under the stars = retro romance. 

• Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Bridgeport: Skyhunters in Flight at Connecticut's Beardsley Zoo(11am-2pm) 
• Bridgeport: Jerry Seinfeld at Hartford HealthCare Amp(8pm) 
• Bridgeport: ZAC N FRIED LIVE at Boca Oyster Bar(8:30pm) 
• Bethel: BluesyLand LIVE at Broken Symmetry(6pm) 
• Danbury: Stella Blues Band LIVE at Sugar Hollow(8:30pm) 
• Fairfield: Silver Steel at Sherman Green Gazebo (6:30-8pm) 
• Farmington: 5th Annual Summer Farm Festival with Art & Craft Fair(10am-4pm) 
• Goshen: Podunk Bluegrass Music Festival(11am) 
• Hartford: CT WITCHFEST(10am-5pm) 
• Mystic: Mystic Outdoor Art Festival(11am-5pm) 
• Newbury, NH: Annual Craftsmen’s Fair at Mount Sunapee Resort in Newbury, NH(8:30am) 
• Newtown: Mini Cheesecakes & Sweet Wines Pairing at Aquila's Nest Vineyards(12pm) 
• Newtown: A Minecraft Movie (PG) at Edmond Town Hall(1pm-7:30pm) 
• Newtown: Jared Cowen & Friends LIVE at Newsylum Brewing Co(3pm-6pm) 
• Newtown: Sinatra & Dino Rat Pack Tribute Show at Aquila’s Nest Vineyards(6pm-9pm) 
• Newtown: Sound Dog LIVE at Perfusion(8pm-11pm) 
• Newtown: ETH DRIVE-IN: The Big Lebowski (R)(9pm) 
• New Canaan: Retro Express LIVE at Gates(8:30pm-11:30pm) 
• New Milford: The Rakes LIVE at Housatonic River Brewing(7pm-10pm) 
• Norwalk: Badboy LIVE at 314 Beer Garden(7:30pm-10:45pm) 
• Ridgefield: The Touro Band LIVE at Nod Hill Brewery(5pm) 
• Ridgefield: Live Music with Present Company at 850 Degree(6pm) 
• Stamford: Early Bird Comedy at New York Comedy Club Stamford(4:30pm)   
• Stamford: Comedian Kevin Nealon at New York Comedy Club Stamford(7pm-9:30pm) 
• Stamford: Open Play Chess in Latham Park – Stamford(1pm-3pm) 
• Stamford: Live Music by Shell Shock't at The Beer Garden (Shippan Landing)(5pm-8pm) 
• Stamford: Not My Problem LIVE at Trirnans Bar(9:30pm) 
• Stamford: Live Music at Third Place: Sun People Funk(2pm-5pm) 
• Stamford: Live Music with The Last Hoorah at Tigin Irish Pub(10pm) 
• Stratford: Jason Schod LIVE at Outriggers(5:30pm-8:30pm) 
• Stratford: Live Music with Tin Sandwich at Windmill Tavern(8pm) 
• Stratford:Get Poison’d Tribute Band LIVE at Joey C’s Boathouse(9pm-12am) 
• Westport: Vinnie Ferrone at Music on Church Lane(6:00pm – 9:00pm) 
• Westport: Adrian Quesada’s Boleros Psicodélicos LIVE at Levitt Pavilion(7:30pm) 
• Wolcott: Wolcott Country Fair(10am-11pm) 
• Woodbury: All Revved Up LIVE at Woodbury Brewing Company(8:30pm)