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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)
Celebrate 3 years of laughs on March 1 at 4:30 PM with a special matinee showcase featuring top comics, great vibes, and nonstop stand-up fun.
Connecticut folk-rock favorites The Moonrise Cartel bring soaring harmonies and high-energy Americana to Daryl’s House in Pawling, NY on April 9. Get tickets now.
Enjoy a free “Blues & Beyond” concert at First Congregational Church of Stamford in Stamford, exploring African American history through music. Reserve seats now.
Join Team Woofgang & Co. for Bunco Blast on Feb 26—games, drinks, and fun supporting adults with disabilities. First session sold out; limited spots left for the 2nd session!
Experience Drew Angus live at SHU Community Theatre March 21 for a powerful night of timeless rock and storytelling.
Best-selling author Claire Dederer joins Hilarie M. Sheets at Verso Fest'26 - March 28th to discuss Monsters: A Fan’s Dilemma and the ethics of art.