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"Can't-Miss Concerts, Festivals, & Fairs in and around Fairfield County: Your Ultimate Guide to Summer Fun!"
Local summer concerts may be winding down, but the fun isn’t stopping! 🍉🎶 With festivals, carnivals, and plenty of fruit and vegetable picking in full swing, this week is packed with events across the region. 🌻🎡 Whether you’re in the mood for some live music, want to indulge in delicious food, or looking for a family-friendly day out, we’ve got you covered. Pick your town, pick your event, click for updates, and GO! 🚗✨
Tuesday, August 20
- Bridgeport: Tangled Vine – St. Ann’s Church – 481 Brewster St (6:30-8:30pm)
- Derby: Silver Steel Band – Derby Green – 105 Elizabeth St (7-9pm)
- Newtown/Sandy Hook: NYC's Jazzy R&B Soulful Sounds & Wine – Aquila's Nest Vineyards – 56 Pole Bridge Rd (6pm-9pm)
- Norwalk: Open Jam in Freese Park (7-10pm)
- Oxford: Nashville Drive – Jackson cove Town Park – 98 Jackson Cove Rd (6:30pm)
- Ridgefield: Sue Foley Trio – Ballard Park – 485 Main St (7-9pm)
- Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stratford: Afinke Band – Paradise Green – 121 Huntington Rd (7pm)
- Trumbull: Floydian Trip – Trumbull Town Green & Gazebo – 5866 Main St (7pm)
- Westport: LaMP (Russ Lawton, Scott Metzger, Ray Paczkowski) - Levitt Pavilion – 40 Jesup Rd (7pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-10pm)
Wednesday, August 21
- Danbury: San Gennaro Festival – Danbury City Center Green – 1 Ives St (5-11pm)
- Greenwich: Billy and The Showmen – Roger Sherman Baldwin Park – 100 Arch St (7pm)
- New Canaan: Fairfield Counts Band – Waveny Park – 677 South Ave (7:30pm)
- Norwalk: The Sound Waves – Pinkney Park – 177 Rowayton Ave (5:30 pm)
- Norwalk: The Stevie Experience – Calf Pasture Beach – Calf Pasture Rd (7:30pm)
- Shelton: The Bernadettes – Shelton Huntington Green – Huntington St. (7pm)
- Southbury: Deuces Wild Duo – River Glen Health Care Center – 162 S. Britain Rd (6:30pm)
- Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stamford: Comedian Heather Shaw – New York Comedy Club Stamford – 230 Tresser Blvd (7pm)
- Westport: Lobesterfest at Campo Beach (3-7pm)
- Westport: Miss Tutti & The Fruity Band – Children's Series –Levitt Pavilion 40 Jesup Rd (7pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-10pm)
Thursday, August 22
- Bridgeport: Impractical Jokers – Hartford HealthCare Amphitheatre – 500 Broad St (7:30pm)
- Brooklyn: Brooklyn Fair – 15 Fairgrounds Rd - (4pm-11pm)
- Danbury: San Gennaro Festival – Danbury City Center Green – 1 Ives St (5-11pm)
- Fairfield: Donavon Frankenreiter – The Lot at FTC – 70 Sanford St (8pm)
- Greenwich: Sun Kings (A Beatles Tribute) - Greenwich Historical Society – 47 Strickland Rd (6:30pm)
- New Fairfield: Split Decision Band – New Fairfield Gazebo – Rt 39 (6:30pm)
- New Milford: The Pop Rocks – Downtown New Milford – 25 Main St (6:30-8:30pm)
- Newtown/Sandy Hook: Sean McNamara Duo – Aquila's Nest Vineyards – 56 Pole Bridge Rd (5:30-8:30pm)
- Newtown/Sandy Hook: Wine & Wheels Car Show – Aquila's Nest Vineyards – 56 Pole Bridge Rd (6pm)
- Orange: West Rocks – Orange Fairgrounds – 525 Orange Center Rd (6-8pm)
- Ridgefield: The Steel Wheels – Ballard Park – 485 Main St (7-9pm)
- Stamford: Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stamford: Fred & Ethal – Street Beats – Bedford Street (6-8pm)
- Stamford: The Mojomatics – Street Beats – Columbus Park – Main St (6-8pm)
- Stamford: Vicky Dussich & Friends – Street Beats – Lower Summer St (6-8pm)
- Stamford: Comedian Ahren Belisle “America's got Talent” - New York Comedy Club Stamford – 230 Tressler Blvd (7pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-10pm)
Friday, August 23
- Bridgeport: John Goode – National Association of Naval Veterans – 69 Brewster St. (5:30-8:30pm)
- Bridgeport: Tedeschi Trucks Band w/special guest Margo Price – Hartford HealthCare Ampitheater – 500 Broad St. (7pm)
- Brookfield: Dan’s Garage – Brookfield Town Hall – 100 Pocono Rd (6:30pm)
- Brooklyn: Brooklyn Fair – 15 Fairgrounds Rd - (10am-11pm)
- Chester: Chester Fair – 11 Kirtland Terrace (6pm-11pm)
- Danbury: San Gennaro Festival – Danbury City Center Green – 1 Ives St (5-11pm)
- Newtown/Sandy Hook: Filo Fox – Aquila's Nest Vineyards – 56 Pole Bridge Rd (6pm)
- Newtown/Sandy Hook: Family Glow Nights – Aquila's Nest Vineyards –56 Pole Bridge Rd (6:30pm)
- Shelton: Dan Carlucci – Jones Family Farms – 606 Walnut Tree Hill Rd (5-7pm)
- Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stamford: Comedian Aida Rodriguez – New York Comedy Club Stamford –230 Tresser Blvd (7pm & 9:30pm)
- Westport: Steve Keith – Music on Church Lane (6pm-9pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-10pm)
Saturday, August 24
- Black Rock: PorchFest at Norden Club – 4 Seabright Ave (11am – 8pm)
- Bridgeport: Skateport Roller Skating Event – 1155 Main St (4pm-8pm)
- Bridgeport: Tedeschi Trucks Band w/special guest Margo Price – Hartford HealthCare Ampitheater – 500 Broad St. (7pm)
- Brooklyn: Brooklyn Fair – 15 Fairgrounds Rd - (9am-11pm)
- Chester: Chester Fair – 11 Kirtland Terrace (8am-11pm)
- Clinton: SummerFest & Fireworks – 1 Waterside Lane (4pm-9pm)
- Danbury: San Gennaro Festival – Danbury City Center Green – 1 Ives St (1-11pm)
- Fairfield: Greenfield Hill Grange Agricultural Fair – 1873 Hillside Rd (10am-3pm)
- Fairfield: DNR – Sherman Town Green – 1451 Post Rd (6:30pm)
- Newtown/Sandy Hook: Tony & The West Siders – Aquila's Nest Vineyards – 56 Pole Bridge Rd (2:30-5:30pm)
- New Haven: International Cultural Arts Fusion Festival – Edgewood Park –Edgewood Ave (11am-5pm)
- New Milford: ACE & Friends – New Milford Town Green – 25 Main St (7pm)
- Norwalk: Pisani Music Co ft. Ms. Rhonda Denet – Calf Pasture Beach (7pm)
- Southbury: CT Arts & Eats – Southbury Town Hall – 501 Main St. S (10am-4pm)
- Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stamford: Comedian Je Devito – New York Comedy Club Stamford – 230 Tessler Blvd (7pm)
- Stamford: Comedy Showcase with Kristal Adams, Maximilian Spinelli, J.P. Mcdade, Max Antonucci at New York Comedy Club Stamford - 230 Tresser Blvd (9:30pm)
- Westport: Madelyn Spera – Church Lane (6pm-9pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-10pm)
Sunday, August 25
- Bridgeport: Ear Candy Duo – National Assoc. Of Naval Vets – 69 Brewster St (3pm)
- Brooklyn: Brooklyn Fair – 15 Fairgrounds Rd - (9am-6pm)
- Chester: Chester Fair – 11 Kirtland Terrace (9sm-6pm)
- Danbury: San Gennaro Festival – Danbury City Center Green – 1 Ives St (1-10pm)
- Greenwich: Sound Beach Community Band – Binney Park – 130 Arch St (7pm)
- Milford: Avenue Groove Band – Walnut Beach Pavillion – 353 E Broadway (4pm-7pm)
- Newtown/Sandy Hook: Frandango Trio – Aquila's Nest Vineyards – 56 Pole Bridge Rd (2:30-5:30pm)
- Newtown/Sandy Hook: Comedian Carmen Lagala – Aquila's Nest Vinewards – 56 Pole Bridge Rd (7pm)
- Norwalk: The Barons – Calf Pasture Beach (5pm-7pm)
- Norwalk: Magic – Pinkney Park – 177 Rowayton Ave (5:30pm)
- Redding: Floydian Trip (Pink Floyd) - Redding Town Green – 15 Cross Hwy (6pm-8pm)
- Shelton: Danny Trzcinski – Jones Family Farms – 606 Walnut Tree Hill Rd (2pm-4pm)
- Stamford Downtown Restaurant Weeks – View participating Restaurants
- Stamford: Sun Kings – Bartlett Arboretum – 151 Brookdale Rd (5-7pm)
- Stamford: Very Good Comedy ft: Lorrie Brownstone, Aric Grooms, Sheba Mason, Robert Punchur at New York Comedy Club Stamford-230 Tresser Blvd (7pm)
- Trumbull: Bob Button Band – Trumbull Town Hall & Gazebo – 5866 Main St (4pm)
- Rhinebeck, NY: The Dutchess County Fair – 6636 US-9 (10am-8pm)
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.