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“What’s Happening This Week in and around Fairfield County: Seasonal Picks & Local Highlights”
Fairfield County is bursting with things to do this season, offering a perfect mix of fall charm and local entertainment. From scenic pumpkin and apple picking outings to thrilling haunted attractions, elegant wine pairings, and outstanding live music performances, there’s something for everyone to enjoy. Explore this week’s curated list of happenings in and around Fairfield County and make the most of this vibrant autumn.
Thursday, October 9
- Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(11am-5pm)
- Danbury: Line Dancing every Thursday night at Elicit Brewing Danbury(7pm)
- Danbury: Thursday Open Jam w/ Sugar House LIVE at Sugar Hallow Taproom(8pm-11pm)
- Fairfield: Some Hacks LIVE at The Sinclair(8:30pm)
- Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm)
- Higganum: Pumpkin Patch at Halfinger Farms(9am-6pm)
- Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm)
- 📣Newtown: Brennan Orie LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm)
- Norwalk: Live music with STEVEN KEITH!(5:30pm-8:30pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm)
- South Windsor: Foster Family Farm Corn Maze(10am-6pm)
- Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm)
- Old Greenwich: Mojo LIVE at Bosco's Bar & Grill(9pm-12am)
- Ridgefield: Dr. Caterwaul's Cadre of Clairvoyant Claptraps LIVE at Nod Hill Brewery(6:30pm)
- 📣Stamford: Comedian Phil Hanley at New York Comedy Club Stamford(7pm)
Friday, October 10
- Bridgeport: Gab Kallay LIVE at Port 5(5pm-8:30pm)
- Bethel: SHAWN TAYLOR LIVE at Shakedown Street(6:30pm)
- Bethel: GORJA LIVE at Notch 8(8pm)
- 📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm)
- Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(11am-5pm)
- Cos Cob: The Bar Car Band LIVE at St. Lawrence Society(7pm-10am)
- Danbury: DJ J.R LIVE at Elicit Brewing Danbury(10pm)
- Danbury: Shot Down LIVE at Elicit Brewing Danbury(9pm)
- Danbury: Glenn Roth LIVE at Charter Oak Taproom(6:30pm-8:30pm)
- Fairfield: DJ SKILLZ LIVE at Elicit Brewing Fairfield(10pm)
- Fairfield: Harvest Fair Halloween Haunt(7pm-10pm)
- Fairfield: Rhythm City LIVE at Elicit Brewing Fairfield(8pm)
- Fairfield: The Amish Outlaws LIVE at The Warehouse FTC(8pm)
- Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm)
- Higganum: Pumpkin Patch at Halfinger Farms(9am-6pm)
- Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm)
- 📣Newtown: Yappy Hour - Bring Your Furry Friends at Aquila's Nest Vineyards(6pm)
- 📣Newtown: Arberesh Music with Peppa Marriti Band at Aquila’s Nest Vineyards(6pm)
- Newtown: Birdsey Beers LIVE at Reverie Brewing(6pm-9pm)
- Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm)
- 📣Newtown: Magical Mystery Doors at Edmond Town Hall(8pm-10pm)
- Newtown:Al Rivoli LIVE at Perfusion Bar(8pm-11pm)
- 📣Norwalk: Quinn & Trug LIVE at SONO 1420(6pm-9pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Norwalk: DKP Band LIVE at Odeen’s Norwalk(7pm)
- Norwalk:What Up Funk Band LIVE at 314 Beer Garden(7:30pm-10:30pm)
- North Salem, NY: Mystic Moon at Harvest Moon Farm and Orchards(7pm)
- North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm)
- New Haven: Ghosts of New Haven(7:30pm)
- Rye, NY: Scarded By The Sound at Playland(11pm)
- Ridgefield: Paris Monster LIVE at Nod Hill Brewery(6pm)
- Rowayton: Tin Sandwich LIVE at Sails American Grill(9:30pm)
- Shelton: Pimpinella LIVE at Pier 131(9:30pm)
- Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm)
- 📣Stamford: Comedian Phil Hanley at New York Comedy Club Stamford(7pm-9:30pm)
- 📣Stamford: Trey Kennedy at The Palace Stamford(8pm)
- South Windsor: Foster Family Farm Corn Maze(10am-6pm)
- Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm)
- Westport: Vertigo LIVE at Black Duck Cafe(9:30pm)
Saturday,October 11
- Bethlehem: Garlic & Harvest Festival(9am-6pm)
- Bethel: IRIS LIES LIVE at Shakedown Street(6:30pm)
- Bethel: LOST REBEL LIVE at Notch 8(8pm)
- 📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm)
- Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(10am-5pm)
- Danbury: DJ DOUBLE G LIVE at Elicit Brewing Danbury(10pm)
- Danbury: The Archives LIVE at Elicit Brewing Danbury(9pm)
- Danbury: PIMPINELLA LIVE at Sugar Hallow Taproom(8:30pm)
- Easton: Pumpkin Patch at Silverman's Farm(9am-5pm)
- Fairfield: DJ PUZZO LIVE at Elicit Brewing Fairfield(10pm)
- Fairfield: The Pop Rocks LIVE at Elicit Brewing Fairfield(9pm)
- Fairfield: Struggle Monkey LIVE at Elicit Brewing Fairfield(9pm)
- Fairfield: Symbio – Dinner and Concert(6pm-9pm)
- Fairfield: Roomful of Blues LIVE at StageOne FTC(8pm)
- Goshen: Fall Festival on the Zoo Farm - Action Wildlife Foundation(5pm)
- Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm)
- Higganum: Pumpkin Patch at Halfinger Farms(9am-5pm)
- Hunter, NY: OKTOBERFEST at Hunter Mountain(11am-6pm)
- Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm)
- Lebanon: Adults-Only Halloween Party at The Connecticut Renaissance Faire(6pm-9pm)
- Litchfield: Bunnell Farm Corn Maze & Pumpkin Patch(10am-5pm)
- Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm)
- Milford: WRATHCHILD Iron Maiden tribute at Anthony D's(9:30pm)
- New Canaan: Captain Obvious LIVE at Gates Restaurant & Bar(8:30pm-11:30pm)
- New Canaan: Allman Brothers Tribute @ Carriage Barn Art Center(6pm-10pm)
- New Milford: Scarrybrooke Park CT's Haunted Trail(6pm)
- 📣Newtown: Fall Belgian Chocolate and Wine Pairing at Aquila's Nest Vineyards(12pm)
- 📣Newtown: Sentinel Salt LIVE at Aquila's Nest Vineyards(2pm-5pm)
- Newtown: Lakeside LIVE at Newsylum Brewing(3pm-6pm)
- 📣Newtown: Country Music Tribute ft Casey Wayne at Aquila’s Nest Vineyards(6pm)
- Newtown: MOMbies DJ Night: Raising Spirits & Funds at Aquila's Nest Vineyards(6:30pm)
- Newtown: The Headliners Club featuring Graham Kay, Erin Maguire, Gastor Almonte at Edmond Town Hall(8pm)
- Newtown: Nick DiMaria Jazz Quartet LIVE at Perfusion Bar(8pm-11pm)
- Newtown: Fall Festival at Castle Hill Farm(10am-5pm)
- Norwalk:Live Himalayan Music at Himalaya SoNo(8:30pm)
- Norwalk: Mind The Gap LIVE at 314 Beer Garden(7pm-11pm)
- North Salem, NY: Mystic Moon at Harvest Moon Farm and Orchards(7pm)
- North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm)
- New Haven: Ghosts of New Haven(7:30pm)
- Old Greenwich: Cooked Up LIVE at Bosco's Bar & Grill(9pm-12am)
- Prospect: 21st Annual Town of Prospect Pumpkin Festival(4pm-8pm)
- Redding: Mr. Know It All LIVE at Milestone(8pm)
- Ridgefield: Frank Viele LIVE at Nod Hill Brewery(4pm)
- Shelton: Legends of Fear(7pm)
- Shelton: Happy Sally LIVE at Pier 131(9:30pm-12am)
- Sherman: Cover to Cover LIVE at JCC In Sherman(7pm-9pm)
- Stamford: That's Amore! Italian Fest in Mill River Park(12pm-9pm)
- 📣Stamford: Swan Lake at The Palace Stamford(7pm)
- 📣Stamford: Comedian Phil Hanley at New York Comedy Club Stamford(7pm-9:30pm)
- Stamford: Blood-Manor(6pm-10pm)
- South Windsor: Foster Family Farm Corn Maze(10am-6pm)
- Trumbull: Trumbull Health & Wellness Fair(10am-2pm)
- Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm)
- Wilton: Beauty is Resistance: art as antidote(11am-6pm)
- Westport: MoCA\CT Sessions: Latinx Musical Identities(7pm-9pm)
- Westport: Pimpinella LIVE at Black Duck Cafe(9:30pm)
- Windsor: Pumpkin Patches, Hay Rides and Mazes / Corn at Brown's Harvest(10am-5pm)
Sunday,October 12
- Bethlehem: Garlic & Harvest Festival(9am-5pm)
- Bridgeport: Sal Grillo LIVE at Port 5(3pm)
- Bethel: BRUNCH - ROBERT FULLERTON LIVE at Shakedown Street(12pm)
- Bethel: Mystery Train LIVE at Notch 8(4pm)
- Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(10am-5pm)
- Danbury: Pets in the Park(11am-4pm)
- Danbury: Dirty Doorknockers + Dad’s Grill LIVE at Charter Oak Taproom(3pm-5pm)
- Easton: Pumpkin Patch at Silverman's Farm(9am-5pm)
- Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm)
- Higganum: Pumpkin Patch at Halfinger Farms(9am-5pm)
- Hunter, NY: OKTOBERFEST at Hunter Mountain(11am-6pm)
- Lebanon: 27th Annual Connecticut Renaissance Faire(10:30pm-6pm)
- Litchfield: Bunnell Farm Corn Maze & Pumpkin Patch(10am-5pm)
- Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm)
- Newtown: Chris Cavaliere LIVE at Reverie Brewing(2pm-5pm)
- Newtown: Jeff Summa & The Roasters LIVE at Newsylum Brewing(2pm-5pm)
- 📣Newtown: Tony & The West Siders LIVE at Aquila's Nest Vineyards(2pm-5pm)
- 📣Newtown: Fleetwood Mac Tribute Show at Aquila’s Nest Vineyards(6pm)
- Newtown: Fall Festival at Castle Hill Farm(10am-5pm)
- Norwalk: Traffic Jam LIVE at 314 Beer Garden(3pm-6pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- New Haven: Ghosts of New Haven(7:30pm)
- Ridgefield: Dan Tressler & Friends LIVE at Nod Hill Brewery(2pm)
- Stamford: That's Amore! Italian Fest in Mill River Park(12pm-9pm)
- Wilton: Beauty is Resistance: art as antidote(11am-6pm)
- Windsor: Pumpkin Patches, Hay Rides and Mazes / Corn at Brown's Harvest(10am-5pm)


Westport, CT - Verso Studios, the media arm of The Westport Library, is excited to announce its first-ever Battle of the Bands , an electrifying live music event celebrating the next generation of Fairfield County talent. Taking place Saturday, January 10, in the Library’s incomparable Trefz Forum, the high-energy showcase will feature four standout teen and college-aged bands: The Breakers, Clockwork, Caravan, and MOSS . Doors open at 7 pm , with the show beginning at 8 pm . Tickets are $10 for students and $20 for general admission, and can be purchased here . More than just a concert, this interactive competition puts the outcome entirely in the hands of the audience. Attendees will vote at the end of the night to determine the winner, awarding a $500 grand prize to first place and $250 to second place. Verso Studios is dedicated to amplifying creativity, collaboration, and community, and the debut of this Battle of the Bands marks an exciting new initiative in support of local live music. The event brings together emerging artists and music fans for a night that celebrates original sound, high-energy performance, and grassroots support for the local music scene. Whether attendees come to support a favorite band or discover something new, the event promises an unforgettable experience where community engagement plays a central role. Event Details Location: Trefz Forum, The Westport Library, 20 Jesup Road, Westport, CT 06880 Doors: 7 pm Show: 8 pm Bands: The Breakers, Clockwork, Caravan, MOSS Audience-voted competition with cash prizes Tickets and additional information: https://westportlibrary.org/event/verso-studios-presents-battle-of-the-bands/

Brookfield Film Festival: A Small Town with a Big Film Legacy Brookfield, CT - Brookfield, Connecticut may be a small town, but it holds a meaningful place in the regional film community. Located in Fairfield County within the southern foothills of the Berkshire Mountains, Brookfield is bordered by Candlewood Lake and Lake Lillinonah and sits just 43 miles northeast of New York City. With a population of approximately 17,000, the town has become a welcoming hub for independent filmmakers. Now in its 18th year, the Brookfield Film Festival continues to gain momentum inside the historic Brookfield Theatre for the Arts. Sponsored by the all-volunteer Brookfield Arts Commission, the festival not only celebrates independent film, but also supports arts education. Proceeds benefit the Brookfield Arts Commission Arts Scholarship Award, presented annually to a graduating Brookfield high school senior pursuing a degree in the arts. This year’s two-day festival features four curated program blocks. Regional Indie Afternoon showcases films from Connecticut and neighboring states, followed by filmmaker Q&A discussions. Read-Through Indie Morning, presented with the Brookfield Theatre for the Arts, gives screenwriters the opportunity to hear their work read aloud and network with actors and filmmakers in a collaborative setting, complete with complimentary coffee and pastries. Shorts and to the Point highlights a handpicked selection of Oscar-nominated and award-winning short films, while Music Indie Evening features original music videos from regional artists and filmmakers. The Brookfield Film Festival takes place March 27 through March 29 at the Brookfield Theatre for the Arts, located at 184 Whisconier Road in Brookfield, CT. A $15 suggested donation supports festival programming and scholarships. Light refreshments and festival merchandise will be available throughout the weekend. With its intimate atmosphere, diverse programming, and strong community focus, the Brookfield Film Festival proves that big creative impact can come from a small town.

Stamford, Ct - Stamford Downtown is excited to announce the return of the beloved Fire & Ice Winter Festival , bringing warmth, artistry, and winter fun back to Columbus Park on Saturday, January 24, 2026, from 1:00 to 5:00 PM . A favorite seasonal tradition, Fire & Ice offers a dynamic afternoon for all ages. Visitors can gather around cozy fire pits, watch live ice sculpting demonstrations by talented professional artists, and enjoy live music throughout the park. Nearby Columbus Park restaurants will add to the experience with inviting indoor and outdoor dining options, creating a lively and welcoming winter atmosphere. This FREE community festival celebrates the best of winter in Stamford Downtown—bundled-up fun, glowing fires, sparkling ice, and shared moments. Don’t miss this signature winter event!



