Plan Your Perfect Week! Top Events in Fairfield County (July 27–Aug 2, 2025)

Get ready for another jam-packed week of fun in Fairfield County! From vibrant food and arts festivals to outdoor concerts, vineyard experiences, comedy shows, and family-friendly events, there’s something happening every single day. Whether you're sipping wine under the stars, jamming to tribute bands, laughing with top comedians, or exploring craft markets and pickle fests, this week (Sunday, July 27 – Saturday, August 2, 2025) is bursting with ways to soak up summer. We’ve highlighted the top three can’t-miss events each day—plus a full roundup of what’s going on—so you can plan your perfect week around your town. 

🌞 Sunday, July 27 

🔥 Highlighted Events: 

• 🎨 Stamford Arts Festival (10am–5pm) – Shop fine arts and crafts in the heart of Mill River Park! 
• 🥒 Connecticut Pickle Festival at Mohegan Sun (11am–8pm) – Pickles, music, and fun all in one crunchy celebration! 
• 🍷 Elton John Tribute Show at Aquila's Nest Vineyards (6pm) – Wine, scenery, and the Rocket Man! 

More Sunday Fun: 

• 🦁 Beardsley Zoo – Now Part of the CT Season Pass! (10am) 
• 🚗 Cruise-In Car Show at Two Roads Brewing (9am–1pm) 
• 🍷 Cheese & Wine Pairing, 🥃 Fine Cigars Night at Aquila’s Nest 
• 🌮 HEY STAMFORD! Food Festival (12pm) 
• 🎭 Comedy Night at NY Comedy Club Stamford (7pm) 
• 🎡 St. Ann Feast '25 (3pm–8pm) 

Live music at Port 5, Castle Black Rock, Dragonfly, Bad Sons Brewery, Jones Winery, Stonebridge, Walnut Beach, and more! 

• Bridgeport: Andy & Scott at Port 5 (3pm) 
• ⭐ Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Bridgeport: Joe Salvati LIVE at The Castle Black Rock(5pm-8pm) 
• Bethel: Ramblin Dan Stevens Sunday LIVE at Dragonfly(1pm) 
• Derby: Anthony David LIVE at Badsons Brewery(2pm-5pm) 
• Easton: Dan Tressler & Friends at Easton Concerts on the Hill(6-8 PM) 
• Fairfield: BackBeat at Fairfield Sherman Green Gazebo (6:30-8pm)   
• Greenwich: SOUND BEACH COMMUNITY BAND at Binney Park(7pm) 
• ⭐ Lebanon: Lebanon Country Fair Weekend (3-11pm) 
• Milford: STONEBRIDGE ALL STAR BAND LIVE at Stonebridge(5pm) 
• Milford: Remember September at Walnut Beach Concerts (4-7pm) 
• ⭐ Montville:  Connecticut Pickle Festival at Mohegan Sun (11am - 8pm) 
• ⭐Newtown: R&R Duo at Aquila’s Nest Vineyards(2–5 PM) 
• ⭐Newtown: Local Cheese & Wine Pairing at Aquila's Nest Vineyards(12pm) 
• ⭐Newtown: Fine Cigars Night at Aquila's Nest Vineyards(5:30pm) 
• ⭐ Newtown: Elton John Tribute Show at Aquila's Nest Vineyards(6pm) 
• ⭐ Newtown: The Lord of the Rings: The War of the Rohirrim (PG-13) at Edmond Town Hall(1pm) 
• Newtown: Judson Jazz LIVE at Reverie Brewing Company(2pm-5pm) 
• Newtown: The Fall River Line Band at Newsylum Brewing Co(2pm-5pm) 
• Norwalk: Silver Steele Band at Calf Pasture Beach(5:00pm – 7:00pm) 
• Norwalk: Neal Francis w/Gavin McGee at Bayley Beach(5:30PM) 
• Norwalk: The Low Darts LIVE at 314 Beer Garden(3pm-6pm) 
• ⭐ Norwalk: St. Ann Feast '25(3pm-8pm) 
• Norwalk: Neal Francis w/Gavin McGee at Bayley Beach(5:30pm) 
• ⭐Stamford: Maria Tiscia and Rio Bound at Bartlett Arboretum & Gardens (5-7pm) 
• Stamford: HEY STAMFORD FOOD FESTIVAL in Mill River Park(12pm) 
• ⭐ Stamford: Comedians Dan St. Germain, Divya Gunasekaran, Max Antonucci, Courtney Fearrington at New York Comedy Club Stamford(7pm) 
• ⭐Stamford: Stamford Arts Festival(10am-5pm) 
• Shelton: Elle Sera at Jones Winery(2–4pm) 
• Shelton: Billy G and Friends LIVE at Spotted Horse Tavern Shelton, Ct.(4pm) 
• Shelton: Tangled Vine LIVE at Pier131 Kitchen + Bar(5:30pm) 
• Stratford: Cruise-In Car Show LIVE at Two Roads Brewing(9am-1pm) 
• Stratford: Christina + Gab LIVE at Blackbird’s Nest!(11am-2pm) 
• Stratford: Frank Chiafari LIVE at Outriggers(2pm-5pm) 
• Stratford: Mighty Souldrivers LIVE at Joey C's Boathouse Cantina & Grill(3pm) 
• Trumbull: The Kenn Morr Band at Trumbull Sunday Concert Series at Town Gazebo(4:00 PM) 
• Washington: Champian Fulton Trio at the Litchfield Jazz Festival (Jazz Brunch)(12 pm) 
• Washington: 30th Annual Litchfield Jazz Festival(12:00pm) 
• Weston: Summer Sundays at Weston History & Culture Center(1pm-4pm) 
• Weston: Hitch and the Giddyup at Weston History & Culture Center's Music at the Barn(5:30pm-7pm) 
• Westport: Hot Club of Black Rock LIVE at Walrus Alley(5pm-7:30pm) 
• Westport: Leonardo Suarez-Paz: Piazzolla100 TANGO LIVE at Levitt Pavilion(7pm) 
• Woodbury: Cris Vitarello and the Brewmasters LIVE at Woodbury Brewing Company(8:30pm) 

🎶 Monday, July 28 

🔥 Highlighted Events: 

• 🐯 Beardsley Zoo – Now Part of the CT Season Pass! (10am) 
• 🎸 Jukebox 45 at Southbury Outdoor Summer Concerts (6pm) 
• 🎤😄 Open Mic Night at New York Comedy Club Stamford (7:30pm) 

🎤 Tuesday, July 29 

🔥 Highlighted Events: 

• 🍕🍷 Pizza Making Class at Aquila’s Nest Vineyards (5:30pm) –  perfect pairing! 
• 🎶 One Bad Oyster at Black Rock Summer Concert Series (6:30pm) 
• 🎸 Junco Partners at Ballard Park (7pm) 

More Tuesday Treats: 

• 🧒 Lynn Lewis & Friends – Newtown Kids’ Concerts (11am) 
• 🎨 Sunny Train Kids’ Series – Trumbull (10am) 
• 🎷 Connecticut Ballet at Levitt Pavilion (7:30pm) 

🎶 Live music  in Stamford, Oxford, Trumbull and more! 

• Bridgeport: One Bad Oyster at Black Rock Summer Concert Series(6:30pm – 8:30pm) 
• Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Newtown: Lynn Lewis and Friends at Newtown's Tuesday Tunes Kids' Concerts(11 AM - 12 PM) 
• Newtown: Pizza Making Class at Mangia Mi East at Aquila's Nest Vineyards(5:30pm) 
• Oxford: Luke James Band at Jackson Cove Summer Concert(6:30pm) 
• Ridgefield: Junco Partners at Ballard Park(7:00 PM)   
• Stamford: PJ Boatwright aka Purvis at 355 Atlantic Street(6pm-8pm) 
• Stamford: Tim Brandt at Ferguson Library Plaza(6pm-8pm) 
• Stamford: Maria Tiscia is Rio Bound at Villa Italia Stamford(6:30pm) 
• Trumbull: The Barons at Trumbull Summer Concert Series(7:00 pm) 
• Trumbull: Sunny Train Music LIVE at Trumbull's Kids Summer Concerts(10:00am) 
• Westport: Connecticut Ballet LIVE at Levitt Pavilion(7:30pm) 

🎺 Wednesday, July 30 

🔥 Highlighted Events: 

• 🎶 TOTO, Christopher Cross & Men at Work at Hartford HealthCare Amphitheater (6:45pm) 
• 🧈 Peanut Butter Jam with Al Decant at Fairfield Sherman Green Gazebo (10:15am–11am) 
• 🍷 Fairfield Alumni Happy Hour at Aquila's Nest (6pm) 

More Wednesday Events: 

• 🔔 Carillon Concert in Danbury (1pm) 
• 🎭 Open Mic at Third Place by Half Full Brewery (7pm) 
• 🎶 Epic Soul at Calf Pasture, Anthem in Shelton, Gunsmoke in Greenwich, and more! 
• Amp(6:45pm) 
• Bethel: Rick Reyes & The Buena Vista Social Club Tribute at La Zingara(7pm) 
• Danbury: Carillon Concert Series: Kristin O'Conner Vece(1pm-2pm) 
• Fairfield: Peanut Butter Jam Concert with Al Decant & Joy Blooms at the Sherman Green Gazebo(10:15 AM – 11:00 AM) 
• Fairfield: Mixtape Match at Elicit(7pm) 
• Greenwich: Gunsmoke at Roger Sherman Baldwin Park (7pm) 
• Monroe: Steve Elci at Family Character Night Series(5:30pm-7pm) 
• Norwalk: Epic Soul at Calf Pasture Beach (7:00 pm) 
• Newtown: Fairfield Alumni Happy Hour at Aquila's Nest Vineyards(6pm) 
• Stamford: Wednesday Night Comedy at New York Comedy Club Stamford (7pm) 
• Stamford: Open Mic LIVE at Third Place by Half Full Brewery(7pm-9pm) 
• Shelton: Anthem at Music Under the Stars Summer Concert Series(7pm) 
• Westport: Flor Bromley :: Children’s Series LIVE at Levitt Pavilion(7pm)

😂 Thursday, July 31 

🔥 Highlighted Events: 

• 😂That’s Fair Comedy at SONO 1420 (8pm) – Local comedians take the stage at the distillery! 
• 🍷 Tarot Reading + Pinot & Pilates at Aquila’s Nest (6pm) 
• 🎶 The Geoff Hartwell Band at Waveny Park (7:30pm) 

More Thursday Highlights: 

• 🌿 Stamford Standards at Veterans Park (6pm) 
• 🏛️ Weston Summer Thursdays (1pm–4pm) 

🎶 Live Jazz, Havana Night, and Acoustic evenings in Milford, Wilton, Ridgefield and more! 

• Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Bridgeport: Hurley Hour LIVE at BRYAC Black Rock(6pm) 
• Bridgeport: Nick Fesko LIVE at The Castle Black Rock(7pm-10pm) 
• Fairfield: The Low Darts at Sherman Green Gazebo (6:30-8pm) 
• Fairfield: Affinity Big Band LIVE at Elicit Brewing(6:30pm) 
• Fairfield: Some Hacks LIVE at Sinclair(8:30pm) 
• Greenwich: Acoustic Kovac Brothers - LIVE at Clubhouse at the Griff(5pm-8pm) 
• Milford: Terri La Chance LIVE at Cafe Atlantique(5pm) 
• Milford: HAVANA NIGHT LIVE at Stonebridge(6pm) 
• New Canaan: THE GEOFF HARTWELL BAND at Waveny Park (7:30-9:30pm)   
• Newtown: One Track Mind at Newtown Summer Concert Series(6:30 PM - 8 PM) 
• Newtown: Pinot and Pilates at Aquila's Nest Vineyards(6pm) 
• Newtown: Tarot Reading with Jenny Gypsy at Aquila's Nest Vineyards(6pm) 
• Norwalk: THAT'S FAIR COMEDY at SONO 1420 America's Maritime Distillery(8:00pm) 
• Norwalk: Downstairs Joe LIVE at Washington Social(8pm-12pm) 
• Piermont, NY: Jazz Thursdays with Scott Robinson + Kevin Lovejoy at Otto's(6pm-9pm) 
• Ridgefield: Sam Morrow Band at Ballard Park(7:00 PM) 
• Rowayton, CT: Arildo D'Souza LIVE at Sails(6pm-9pm) 
• Stamford: Comedian Nicole Burch New York Comedy Club Stamford(7:00pm) 
• Stamford: Stamford Standards at Veterans Park(6pm-8pm) 
• Stamford: The Modifieds at Columbus Park(6pm-8pm) 
• Stratford: Anthony Edley LIVE at Outriggers(5pm-8pm) 
• Stratford: Rob Glassman Band LIVE at Joey C's Boathouse Cantina & Grill(6pm) 
• Shelton: Jamie Cairney Acoustics LIVE at Caloroso(6pm-9pm) 
• Shelton: Jamie Cairney Acoustics LIVE at Caloroso(6pm-9pm) 
• Weston: Summer Thursdays at Weston History & Culture Center(1pm-4pm) 
• Westport: Argonaut & Wasp w/s/g Wild & Co. LIVE at Levitt Pavilion(7pm) 
• Westport: Jim Royle's Caribbean Jazz Connection at Jazz on Post(7:30pm-10pm) 
• Wilton: Summer Music Concert Series Featuring Captain Obvious(5pm-6:30pm)

🎸 Friday, August 1 

🔥 Highlighted Events: 

• 🎶 Owen Daniel & The Breakers at Music on Church Lane – Westport (6pm–9pm) 
• 🎤 Hooch at Port 5 – Bridgeport (5pm–8:30pm) 
• 🍻 On The Rocks at Woodbury Brewing Co. (8:30pm) 

More Friday Fun: 

• Bridgeport: Hooch at Port 5 (5-8:30 pm)   
• Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Bethlehem: Morgan Skelly & The Old Crows at Friends Friday Summer Concerts at March Farm(6–8 PM)  
• Brookfield: Nashville Drive LIVE at Brookfield's Concerts in the Park(6:30 PM) 
• Danbury: Sister Funk at Danbury's Summer Concert Series(7pm - 9:30pm) 
• Fairfield: Jim Royle’s Caribbean Connection at Jazz Fridays(6:30 PM – 8:00 PM) 
• Monroe: The Future Heavies at Wolfe Park Summer Concert Series(7:30 PM – 9:00 PM) 
• Mahopac, NY: Bon Jovi and Pat Benatar LIVE at Putnam County Golf Course(6:30pm) 
• Milford: Moxanne LIVE at Cafe Atlantique(6:30pm) 
• Newtown: Chocolate Fondue Dip & Sip at Aquila's Nest Vineyards(12pm) 
• Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm) 
• Newtown: DJ JR In The Mix LIVE at Perfusion(8pm-1pm) 
• Newtown: Touchdown Boys Live LIVE at Reverie Brewing(6pm-9pm) 
• Norwalk: Live Music With Geoff Hartwell!(10pm) 
• Ridgefield: The Hot Club of Black Rock LIVE at Nod Hill Brewery(6:30pm) 
• Stamford: Comedian Kevin Herrera at New York Comedy Club Stamford(7:00 pm - 9:30 pm) 
• Shelton: Holley McCreary at Jones Winery(5–7pm) 
• Stratford: Dawn & Greg LIVE at Outriggers(5:30pm-8:30pm) 
• Westport: Owen Daniel & The Breakers at Music on Church Lane(6:00pm – 9:00pm) 
• Woodbury: On The Rocks LIVE at Woodbury Brewing Company(8:30pm) 

🎉 Saturday, August 2 

🔥 Highlighted Events: 

• 🎨 SONO Arts Festival – Norwalk (10am–6pm) 
• 🎭 Disney Drag Music Show at Aquila's Nest (7pm) 
• 🍻 Hop Yard Hoedown at Two Roads Brewing (12pm–4pm) 

Even More Saturday Fun: 

• 🧀 Chocolate Fondue Dip & Sip at Aquila's Nest (12pm) 
• 😂 Early Bird Comedy + Kevin Herrera at NY Comedy Club Stamford 

🎶 Live Music on Church Lane, Shippan Landing, Outriggers, Perfusion, Reverie, and more! 

• Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) 
• Bethel: Bobby Morill LIVE at Broken Symmetry(6pm) 
• Fairfield: Hermann & Company at Sherman Green Gazebo (6:30-8pm) 
• Fairfield: Shakedown Citi LIVE at StageOne in FTC(8pm) 
• Milford: SpacedRum71 LIVE at Cafe Atlantique(6:30pm) 
• Newtown: Disney Drag Music Show at Aquila's Nest Vineyards(7pm) 
• Newtown: Shay Sullivan LIVE at Perfusion(8pm-11pm) 
• Norwalk: Summer Concert with the Silver Steel Band at Norwalk Green Summer Concerts(7:00pm – 9:00pm) 
• Norwalk: SONO Arts Festival(10am-6pm) 
• Ridgefield: Eddy Lee Ryder LIVE at Nod Hill Brewery(5pm) 
• Stamford: Early Bird Comedy at New York Comedy Club Stamford(4:30pm) 
• Stamford: Comedian Kevin Herrera at New York Comedy Club Stamford(7:00pm-9:00pm) 
• Stamford: Live Music by Last Hoorah at The Beer Garden (Shippan Landing)(5pm-8pm) 
• Stratford: Hop Yard Hoedown LIVE at Two Roads Brewing(12pm-4pm) 
• Stratford: Chris Marolda LIVE at Outriggers(5:30pm-8:30pm) 
• Westport: John Richers at Music on Church Lane(6:00pm – 9:00pm) 
• Woodbury: Crossfire Hurricane LIVE at Woodbury Brewing Company(8:30pm)