Looking for the best ways to spend your weekend in and around Fairfield County? From live music and comedy to fairs, festivals, and family fun 🎡👨‍👩‍👧, there’s something for everyone. Here are the top picks for each day, Wednesday through Sunday: Wednesday, September 3 🎶 Charlie Apicella & Iron City LIVE – Catch this jazz-soul fusion at La Zingara in Bethel (7–9:15pm). 🦁 Beardsley Zoo Joins the CT Season Pass – A family-friendly outing in Bridgeport (10am). 🎶 The Short Bus Band at Waveny Park – Free outdoor concert in New Canaan (7:30–9:30pm). 📣 Newtown: Book Signing with Author Maria Flores at Aquila's Nest Vineyards(6pm) 📣 Newtown: Salsa & Bachata Dance Night at Aquila's Nest Vineyards(6pm) 📣 Newtown: Sunset Sound Bath at Aquila's Nest Vineyards(6:30pm) Stamford: Open Play Chess in Veterans Memorial Park – Stamford(12pm-2pm) Stamford: Jazz Trio in Kiwanis Park(6pm) 📣 Stamford: Comedians James Goff, Lauren Hope Krass, Joe Mahoney, Ben Kirschenbaum at New York Comedy Club Stamford (7pm) Thursday, September 4 🎶 Sun Kings: A Beatles Tribute – Live on the Great Lawn in Cos Cob (6:30–8pm). 🎡 North Haven Fair – Classic rides, games, and fair food (5–10pm). 😂📣 Josh Wolf: The Campfire Tour – Nationally known comedian at Edmond Town Hall, Newtown (8–10pm). Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) Danbury: Line Dancing at Elicit Brewing Danbury(7pm) Danbury: Thursday Open Jam w/ Sugar House LIVE at Sugar Hollow Taproom(8pm-11pm) Fairfield: Fai Laci W/ The Tines | Showpony LIVE at StageOne FTC(7pm) Fairfield: CT Seaport Car Club's Car Cruises at Elicit Brewing Fairfield(5pm) New Canaan: THE EFFECT(7:30pm) 📣Newtown: Llamas and Llibations at Aquila's Nest Vineyards(5:30pm) 📣Newtown: Emma Henning LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) 📣Newtown: Wine, Words & Wisdom Book Club Series at Aquila's Nest Vineyards(6:30pm) 📣Newtown: Glen Roth LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) Old Greenwich: Mojo LIVE at Bosco's Bar and Grill(9pm-12am) Ridgefield: Ramblin' Dan Stevens LIVE at Nod Hill Brewery(6:30pm) Sherman: Open Mic Night - JCC in Sherman(6:30pm-8:45pm) Weston: Summer Thursdays at Weston History & Culture Center(1pm-4pm) Friday, September 5 🎡📣 Norwalk Oyster Festival – A beloved tradition with music, food, and fun (6–11pm). 🎶📣 Eliot Lewis (from Hall & Oates) LIVE – Reverie Brewing, Newtown (7–10pm). 🎤📣 Funny Marco – Comedy night at New York Comedy Club, Stamford (7–9pm). Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) Bridgeport: Ethyl Flying Solo LIVE at Port 5(5pm-8:30pm) Bethlehem: Bethlehem Fair(5pm-10pm) Bethel: BARN RATS LIVE at Notch8(8pm) 📣Danbury: Danbury’s Brazilian Festival(12pm-10pm) Danbury: Five to One w/ Bad Spell LIVE at Sugar Hollow Taproom(8:30pm) Fairfield: Jukebox Radio at Elicit Brewing Fairfield(9pm) North Haven: North Haven Fair(3pm-11pm) Naugatuck: St. Michael's Village Green Fair – Naugatuck(10am-8pm) Newtown: Jessi Rose LIVE at Perfusion Bar(8-11pm) 📣Newtown: Round Two Acoustical Duo LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) 📣Newtown: Friends & Family Glow Night in the Vines at Aquila's Nest Vineyards(6pm) 📣Newtown: Girl Scout Cookies & Wine Pairing at Aquila's Nest Vineyards(6pm) 📣Newtown: Local Cheese & Wine Pairing at Aquila's Nest Vineyards(6pm) 📣Newtown : Bobby Wheeler LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm) Newtown: Eliot Lewis (From Hall & Oates) LIVE at Reverie Brewing(7pm-10pm) 📣Norwalk: Oyster Festival(6pm-11pm) Norwalk: Geoff Hartwell at O'Neils(10pm) 📣Norwalk: Henry Jones LIVE at SONO 1420(6pm-9pm) Norwalk: Sonic Bullet LIVE at 314 Beer Garden(7:30pm-10:30pm) Old Greenwich: The Wankers LIVE at Bosco's Bar and Grill(9pm-12am) Ridgefield: Brian Dolzani LIVE at Nod Hill Brewery(6:30pm) Redding: Mike Milazzo LIVE at The Redding Roadhouse(7pm-10pm) Rowayton: Tangled Vine LIVE at Sails American Grill(9:30pm-12am) Shelton: Carrie Ashton at Jones Winery(5–7pm) Stratford: Jordan LIVE at Outriggers(5:30pm-8:30pm) 😂📣Stamford: Comedian Funny Marco at New York Comedy Club Stamford(7pm-9pm) Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm) 📣Westport: Steve Keith at Music on Church Lane(6:00pm – 9:00pm) Westport: Retro Express LIVE at Black Duck Cafe(9:30pm) Saturday, September 6 🎉📣 14th Annual Health, Wellness & Lifestyle Expo – Stamford’s Harbor Point (10am–5pm). 🎶 Mihali (Full Band Show) – Levitt Pavilion, Westport (5pm). 🎡 North Haven Fair – A full day of rides, food, and entertainment (10am–11pm). Bridgeport: HarborFest w/Shameless at Port 5(3pm) 📣Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) Bridgeport: Bridgeport Green Festival(12pm-6pm) Bridgeport: Ladies Game Day at Port 5 Naval Vets(1pm-3pm) 📣Bethlehem: Bethlehem Fair(8am-9pm) Bethel: ERIK RABASCA LIVE at Shakedown Street(6:30pm) Bethel: LOST REBEL LIVE at Notch8(8pm) 📣Danbury: Danbury’s Brazilian Festival(12pm-8pm) Danbury: Tony & The West Siders at Charter Oak Brewing(4pm-7pm) Danbury: Pimpinella LIVE at Sugar Hollow Taproom(8:30pm) Darien: ZULLY & THE OGS LIVE at The Goose(9pm-12am) Fairfield: Jamie Hulley Arts Foundation presents Jay Stollman and the All-Stars(6:30pm-10pm) Fairfield: The Reverend Peyton's Big Damn Band W/ The Hooten Hallers LIVE at StageOne FTC(7pm) Fairfield: Not My Problem LIVE at Elicit Brewing Fairfield(9pm) Greenwish: Kovac Brothers LIVE at Clubhouse at the Griff(7pm-10pm) Glastonbury: 2025 Glastonbury Fine Art and Craft Show(10am-5pm) Lebanon: 27th Annual Connecticut Renaissance Faire(10:30-6pm) 📣Monroe: St. Peter’s Grace Apple Festival(10am-5pm) 📣Milford: Milford Elks Health & Wellness Fair(10am-5pm) New Canaan: MIND THE GAP LIVE at Gates Restaurants and Bar(11:30pm) 📣Newtown: Cheese Fondue Dip & Sip at Aquila's Nest Vineyards(12pm) 📣Newtown: Mutts Gone Nuts at Edmond Town Hall(2pm-4pm) 📣Newtown: Teacup Sallie LIVE at Aquila's Nest Vineyards(2pm-5pm) 📣Newtown: A Night of Timeless Classics at Aquila’s Nest Vineyards(6pm-9pm) 📣Newtown: Frandango LIVE at Aquila's Nest Vineyards(2:30pm-5:30pm) Newtown: Newtown All Stars ft. Luke Bemand, Ben Atkind, & Jared Sage Cowen LIVE at Reverie Brewing(3pm-6pm) Newtown: Scratch LIVE at Blimp Fest 2025(3pm-6pm) Newtown: Between The Keys LIVE at Perfusion Bar(8-11pm) Norwalk: Ellis Island Band LIVE at 314 Beer Garden(7:30pm-10:45) North Haven: North Haven Fair(10am-11pm) North Branford: North Branford Fall Craft Fair(9am-2pm) 📣New London: CT Maritime Heritage Festival(10am-5pm) Naugatuck: St. Michael's Village Green Fair – Naugatuck(10am-7pm) 📣Norwalk: Oyster Festival(11am-11pm) Ridgefield: Fat Boi's Brass Band LIVE at Nod Hill Brewery(5pm) Redding: Captain Obvious LIVE at Milestone(9pm-12am) Sherman: Sherman Chamber Ensemble at Sherman Summer Concert Series(4:00pm – 7:00pm) Stamford: Open Play Chess in Latham Park – Stamford(1pm-3pm) Stamford: Hot Mezz at The Beer Garden (Shippan Landing)(5pm-8pm) 😂📣Stamford: Comedian Funny Marco at New York Comedy Club Stamford(7pm-9:30pm) Stratford: Chris Marolda LIVE at Outriggers(5:30pm-8:30pm) 📣Southbury: Southbury Celebration(4:30pm-9pm) 📣Westport: Owen Daniel (Solo) at Music on Church Lane(6:00pm – 9:00pm) Westport: MIHALI * Full Band Show * w/s/g Soule Monde and w/ Mr. Mota LIVE at Levitt Pavilion(5pm) Westport: Cooked Up LIVE at Black Duck Cafe(9:30pm) Wethersfield: Wethersfield Cornfest(10am-6pm) Wilton: 'TheDisneyPinventory' Pin Trading Event(11:30am-3pm) Sunday, September 7 🎡 Norwalk Oyster Festival – Family fun, live music, and great seafood (11am–8pm). 🎶 📣 Memories of Patsy – Tribute Show – The Palace Danbury Theatre (3pm). 🐝 Honey Harvest Festival – A sweet day out at Stamford Museum & Nature Center (11am–3pm). Bridgeport: KT Lay LIVE at Port 5( 3:00 PM) Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am) Bridgeport: Peace Talks Reception at Crown Gallery at Metro Art Studios(1pm-3pm) Bridgeport: The Lonetown Boys at Park City Music Hall(6pm-9pm) Bethlehem: Bethlehem Fair(8am-5:30pm) Bethel: DEAN SNELLBACK LIVE at Shakedown Street(12pm) Bethel: FIVE TO ONE LIVE at Notch8(5pm) Danbury: Barry Blumenfield at Charter Oak Brewing(3pm-5pm) Glastonbury: 2025 Glastonbury Fine Art and Craft Show(10am-5pm) Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm) 📣Monroe: St. Peter’s Grace Apple Festival(10am-4pm) New London: CT Maritime Heritage Festival(10am-5pm) North Haven: North Haven Fair(10am-7pm) 📣Newtown: Italian Music Brunch with Primavera Band at Aquila's Nest Vineyards(11:30pm) 📣Newtown: Myron and the Jam Fam LIVE at Aquila's Nest Vineyards(2pm-5pm) 📣Newtown: Tom Petty Tribute Show at Aquila’s Nest Vineyards(6pm-9pm) Newtown: Iris Lies LIVE at Newsylum Brewing Co(2pm-5pm) 📣Norwalk: Oyster Festival(11am-8pm) Norwalk: Fan Fiction LIVE at 314 Beer Garden(2:30pm-6pm) Ridgefield: The Dave Savitsky Trio LIVE at Nod Hill Brewery(2:30pm) Redding: Owen Daniel LIVE at Milestone(4pm-7pm) Redding: Captain Obvious LIVE at Milestone(9pm-12am) Shelton: Dan Carlucci at Jones Winery(2–4pm) Stamford: Honey Harvest Festival(11am-3pm) Weston: Summer Sundays at Weston History & Culture Center(1pm-4pm) Weston: One Bad Oyster at Music at the Barn(5:30pm-7pm) Westport: Amy Irving LIVE at Levitt Pavilion(7pm) 👉 Whether you’re into live concerts, community festivals, or family fun, this week is packed with experiences that bring people together. Grab your friends and family, and make the most of this long list of things to do in and around Fairfield County!

From piano bars to center stage, Sean O’Reilly is redefining the local music scene with a sound that blends harp, piano, and poetic lyricism. Influenced by Tori Amos and Jeff Buckley, Sean’s music fuses classical depth with indie edge—offering a performance that feels more like a conversation than a concert. Catch him September 17, 2025, at Park City Music Hall in Black Rock , where he’ll debut his brand-new five-piece band. Expect lush arrangements, original songs, and a few surprises. 🎟️ Tickets: ParkCityMusicHall.com