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Fun Things To Do This Weekend in and around Fairfield County.
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:
🎶 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)
🎶 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)
🎡📣 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)
🎉📣 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)
🎡 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!
Discover Fairfield County’s best weekend events—from live music to comedy—no holiday themes needed. Enjoy pure fun and great nights out with our curated guide.
Experience the magic of Mannheim Steamroller Christmas on December 7 at The Palace Theatre Stamford. A festive night of timeless holiday music and tradition awaits.
Discover Fairfield County’s top holiday events, including Newtown’s Holiday Festival, sip & shops, tree lightings, festive shows, and Repeal Day celebrations.
Country fans, mark your calendars — Julia Cole is coming to The Palace Theatre Stamford on December 6, 2025, and this is one high-energy show you won’t want to miss. Please note: the originally scheduled September 27 & 28 performances have been rescheduled to December 6 , and all tickets from those dates will be honored. The show has also moved from the UpStage to the Mainstage and will remain general admission . Nashville recording artist Julia Cole continues her rapid rise as one of country music’s most empowering and influential new voices. With over 500 million streams , more than 2 million social followers , and a debut on the Grand Ole Opry , Julia’s star power is undeniable. She’s been named a CMT Next Woman of Country and featured on CMT, SiriusXM, Circle TV, CBS, The CW, and more. Blending authentic country storytelling with real-life moments, Julia’s musical journey began singing the national anthem at her high school volleyball games—eventually performing for NFL, MLB, MLS, NASCAR, and ESPN crowds of 75,000. She’s toured internationally, opening for major acts like Dierks Bentley, Dan + Shay, Jon Pardi, Carrie Underwood, Kenny Chesney, Kane Brown, The Chainsmokers, Lee Brice and more. 🎟️ Tickets are on sale now! Purchase here: palacestamford.org Don’t miss Julia Cole live at The Palace Theatre Stamford’s Mainstage!
Celebrate Repeal Day at SONO 1420 with a Great Gatsby Party featuring Prohibition cocktails, a Land & Sea menu, and live jazz from DTHREE Music.
Enjoy five live jazz performances, gourmet food trucks, and cozy vibes at Aquila’s December Jazz Fest in Newtown, CT. Tickets just $20 for the full weekend.