Fall is calling! Cooler days, changing leaves, apple picking, cider donuts, country fairs, pumpkin patches and fall festivals are returning throughout Connecticut and the Hudson Valley. One of the best things about living in Fairfield County is how many great fall destinations are within an easy drive. You can stay close to home, head toward the Connecticut shoreline or Litchfield Hills, or cross the New York border for a Hudson Valley fall road trip. Fairfield After Dark has rounded up some of our Hot Picks for Fall 2026 . Grab your sweater and start planning! 🍎 FAIRFIELD COUNTY Blue Jay Orchards — Bethel A local fall favorite for pick-your-own apples, pumpkins, a farm market and those must-have cider donuts. Silverman’s Farm — Easton Apple picking, pumpkins, a country market and animal farm make Silverman’s an easy family fall outing. Beardsley’s Cider Mill & Orchard — Shelton Pick apples and stock up on fresh cider, cider donuts, pies and other bakery favorites. Aki Matsuri Fall Festival — Westport | Sept. 19 Japanese culture takes over Jesup Green with taiko drumming, dancing, martial arts, activities and a marketplace. Westoberfest — Westport | Oct. 3 Downtown Westport celebrates Oktoberfest with local and regional beer, live music and fall fun. NICE Festival — Norwalk | Oct. 3 Oyster Shell Park comes alive with international food, music, dance, arts, crafts and cultural performances. 🍏 NEW HAVEN COUNTY Bishop’s Orchards Fall Festival — Guilford | Through Nov. 1 One of FAD’s biggest fall picks with apple picking, a corn maze, wagon rides, pumpkins, food and seasonal activities. Rose Orchards — North Branford Apples, pumpkins, corn maze, wagon rides, farm market and creamery make this a full fall afternoon. Blue Hills Orchard — Wallingford A traditional Connecticut orchard experience with seasonal apple picking and wagon rides. Guilford Fair — Sept. 18–20 A classic agricultural fair with rides, animals, exhibits, food, crafts and entertainment. Orange Country Fair — Sept. 19–20 Old-fashioned country-fair fun filled with agriculture, food, entertainment and family activities. Seymour Pumpkin Festival — Sept. 20 French Memorial Park fills with arts, crafts, food and family activities celebrating fall. Milford Oktoberfest — Sept. 25–26 Head to Fowler Field for beer, food, music and traditional Oktoberfest festivities. 🍂 LITCHFIELD COUNTY Averill Farm — Washington Depot Pick apples and pears while enjoying one of the most picturesque old-fashioned farm experiences in the Litchfield Hills. March Farm — Bethlehem Pick-your-own fruit, a farm market, bakery, animals, corn maze and weekend hayrides. The Farm — Woodbury | Through Oct. 30 Corn maze, pumpkins, hayrides, sunflowers, music and seasonal farm fun. Harwinton Fair — Oct. 2–4 Pig races, tractors, animals, bluegrass, food and plenty of old-fashioned country-fair traditions. Connecticut Garlic & Harvest Festival — Bethlehem | Oct. 10–11 Garlic, harvest foods, vendors and fall festivities take over the Bethlehem Fairgrounds. 🍎 WESTCHESTER COUNTY, NY Harvest Moon Farm & Orchard — North Salem Apple picking meets fall festival with hayrides, live music, cider donuts, seasonal food and pumpkins. Outhouse Orchards — North Salem Apples, pumpkins, corn maze, hayrides and cider donuts make this another North Salem favorite. Stuart’s Fruit Farm — Granite Springs A traditional apple-picking destination with a farm stand, bakery and weekend hayrides. Wilkens Fruit & Fir Farm — Yorktown Heights Apple picking, farm-market goodies and seasonal treats make Wilkens another Westchester fall tradition. 🍎 PUTNAM COUNTY, NY Salinger’s Orchard — Brewster No pick-your-own here, but definitely worth a stop for locally grown apples, cider donuts, pies and its Farm Market & Bakery. 🍏 DUTCHESS / RENSSELAER COUNTIES, NY Fishkill Farms — Hopewell Junction Apple and pumpkin picking, wagon rides, cider donuts, seasonal food and Treasury Cider make this a great Hudson Valley day trip. Goold Hill Estate – Castleton-on-Hudson Goold Hill Estate is now open, welcoming guests for apple picking, family-friendly farm experiences, live music and events, artisan markets, seasonal treats, locally crafted ciders, and a glimpse at its future Estate wines. Barton Orchards — Poughquag Go big with apple and pumpkin picking, family attractions, food, entertainment and fall festival weekends. Meadowbrook Farm — Wappingers Falls A smaller farm experience for apples, pumpkins, cider donuts and seasonal farm-market shopping. Hudson Valley Wine & Food Festival — Rhinebeck Make it a grown-up fall road trip with regional wines, craft beverages, food and Hudson Valley producers. 🍎🍩 FAD’s Fall Advice: Never Skip the Cider Donuts! Whether you stay close to home in Fairfield County, head north into the Litchfield Hills or cross the border into New York, there’s plenty of fall fun waiting within an easy road trip. Remember: Apple varieties, picking conditions, hours and activities can change throughout the season. Check directly with farms and festivals before heading out, especially when pick-your-own apples are the main reason for your visit. Now grab the family, your friends — or your favorite fall date — and go enjoy autumn! Keep checking FairfieldAfterDark.com for more Fall Happenings, Halloween Events, Fairs, Festivals, Live Music and Things To Do in and around Fairfield County.
September 14–20, 2026 Fall entertainment is kicking into high gear, and Fairfield After Dark has your week covered! From comedy and live music to vineyard happenings, a legendary cultural commentator and artisan shopping, there are plenty of reasons to get out this week. Here are FAD’s Top Picks for September 14–20! 🍷 TUESDAY, SEPTEMBER 15 | AQUILA’S NEST VINEYARDS — NEWTOWN Kick off the week at Aquila’s Nest Vineyards with Whispers From Heaven with Patricia Griffin . Enjoy the vineyard setting while checking out one of the many special experiences happening throughout the week. 👉 GET THE DETAILS & PLAN YOUR VISIT HERE 😂 WEDNESDAY, SEPTEMBER 16 | NEW YORK COMEDY CLUB — STAMFORD Need a midweek laugh? Mike Cannon hits the stage at New York Comedy Club Stamford Wednesday at 7 PM . 👉 GRAB YOUR TICKETS HERE 🍷 WEDNESDAY, SEPTEMBER 16 | AQUILA’S NEST VINEYARDS — NEWTOWN Put on those boots and head to Newtown! Country Line Dancing is on the schedule Wednesday at Aquila’s Nest Vineyards. 👉 GET THE DETAILS HERE 💕 WEDNESDAY, SEPTEMBER 16 | ODEEN’S at Oak Hills - Norwalk Meet local singles ages 25–39 face-to-face at ODEEN’S Oak Hills for a fun, low-pressure evening of speed dating, guided conversations, and the chance to make a real connection. 👉 Tickets are limited GRAB YOUR TICKETS HERE 🎹 THURSDAY, SEPTEMBER 17 | THE BILLY JOEL LEGACY — THE PALACE STAMFORD The music of the Piano Man comes alive when The Billy Joel Legacy: A Tribute Experience takes the stage at The Palace Stamford Thursday at 7:30 PM . Billy Joel fans, this one's for you! 👉 GRAB YOUR TICKETS HERE 🍷 THURSDAY, SEPTEMBER 17 | AQUILA’S NEST VINEYARDS — NEWTOWN Aquila’s Nest keeps the week going with several Thursday experiences, including Pilates, Plant Bingo and special workshops . 👉 GET THE DETAILS HERE 🎤 FRIDAY, SEPTEMBER 18 | FRAN LEBOWITZ — EDMOND TOWN HALL, NEWTOWN Known for her razor-sharp wit, unapologetic opinions and hilarious observations on modern life, Fran Lebowitz comes to Edmond Town Hall Friday at 8 PM . Doors open at 7 PM. 👉 GRAB YOUR TICKETS HERE 🎤 FRIDAY, SEPTEMBER 18 | SIMPLY THE BEST — THE PALACE STAMFORD Get ready for the music of Tina Turner! Simply The Best: A Tribute to the Music of Tina Turner takes over The Palace Stamford Friday at 8 PM . 👉 GRAB YOUR TICKETS HERE 😂 FRIDAY, SEPTEMBER 18 | CAITLIN PELUFFO — NEW YORK COMEDY CLUB STAMFORD Start your weekend laughing with Caitlin Peluffo , performing two shows Friday night at 7 PM and 9:30 PM . 👉 GRAB YOUR TICKETS HERE 🦙🍷 FRIDAY, SEPTEMBER 18 | AQUILA’S NEST VINEYARDS — NEWTOWN Friday brings even more fun to Aquila’s Nest with Llamas & Llibations and Cruise Night . 👉 GET THE DETAILS HERE 🛍️ SATURDAY, SEPTEMBER 19 | POP SHOP MARKET — DARIEN COMMONS Shop small and discover something different when PopShop Market returns to Darien Commons Saturday from 11 AM–5 PM . Explore a curated collection of independent makers and small businesses offering apparel, jewelry, home décor, self-care products, gifts and plenty of one-of-a-kind finds. 👉 GET ALL THE DETAILS HERE 😂 SATURDAY, SEPTEMBER 19 | NEW YORK COMEDY CLUB — STAMFORD Saturday starts early with Early Bird Comedy at 4:30 PM , followed by another performance from Caitlin Peluffo at 7 PM . 👉 GRAB YOUR TICKETS HERE 🍷🎸 SATURDAY, SEPTEMBER 19 | THE 80s ROCK EXPERIENCE — AQUILA’S NEST VINEYARDS Turn back the clock at Aquila’s Nest with The 80s Rock Experience Tribute Show , happening Saturday from 6–9 PM . 👉 GRAB YOUR TICKETS & GET THE DETAILS HERE 🎹 SATURDAY, SEPTEMBER 19 | THE MIGHTY FRANKLIN BROTHERS — THE PALACE DANBURY Steely Dan fans, this one's for you! The Mighty Franklin Brothers take over The Palace Danbury Saturday at 7:30 PM . Led by brothers Jay and Carl Franklin and backed by a powerhouse lineup of musicians and horns, the band brings the sophisticated arrangements, soulful vocals and unmistakable sound of Steely Dan to the stage. 👉 GRAB YOUR TICKETS HERE 🎬🎶 SATURDAY, SEPTEMBER 19 | LABYRINTH IN CONCERT — THE PALACE STAMFORD Celebrate 40 years of a cult classic with Jim Henson’s Labyrinth: In Concert — 40th Anniversary at The Palace Stamford Saturday at 7:30 PM. 👉 GRAB YOUR TICKETS HERE 🎶 SUNDAY, SEPTEMBER 20 | GREEN EYED LADY — ODEEN’S OAK HILLS, NORWALK Wrap up the weekend with dinner and live music! Green Eyed Lady performs at Odeen’s Oak Hills Sunday from 4–7 PM . 👉 Make a Reservation here! ⭐ GET OUT & HAVE SOME FUN! From Newtown to Stamford, Darien, Danbury, Ridgefield, New Canaan and Norwalk , there’s plenty happening this week. These are just a few of FAD’s Top Picks — grab your tickets, make those reservations and start planning your week early! 🎶 😂 🍷 🛍️ 🎭 Get Out. Have Fun. Live Local. See even more concerts, comedy, festivals, fairs, fall happenings and Things To Do in and around Fairfield County at FairfieldAfterDark.com.
Milford, CT: Downtown Milford will come alive with the sounds of jazz on Saturday, October 3, 2026 , as the Milford Arts Council presents the inaugural Jazz’n Downtown , a new immersive celebration combining live music, local art, dining and the charm of one of Connecticut’s favorite shoreline downtowns. Presented with lead Presenting Sponsor Coastal Bridge Advisors , Jazz’n Downtown is designed to be explored at your own pace. Visitors can arrive by train, car, boat, bike or foot and spend the day strolling Milford’s historic neighborhoods, waterways, boutiques, restaurants and artisan displays — all while live jazz provides the soundtrack. Jazz Throughout Downtown Milford Award-winning jazz performers will take the stage at three outdoor venues , including locations along Milford’s scenic waterfront. The music continues throughout the downtown experience, with solo and duo jazz performers appearing at participating restaurants during brunch, lunch and dinner. It’s more than a traditional music festival. Jazz’n Downtown brings music, art, food and community together throughout the heart of Milford, allowing guests to create their own experience and discover something new around every corner. An Evening Celebrating Ella & Louis The celebration continues that evening at Parsons Veterans’ Memorial Hall with a special tribute concert honoring two of jazz music’s most legendary performers, Ella Fitzgerald and Louis Armstrong . The evening concert requires a separate ticket, while VIP packages offer an enhanced Jazz’n Downtown experience with reserved seating areas, an early reservation window for brunch, lunch and dinner, parking and reserved seating for the evening concert. About the Milford Arts Council Founded in 1972, the Milford Arts Council (MAC) is a nonprofit organization dedicated to connecting and enriching the community through music, theater, visual arts, dance, film and creative expression. MAC presents more than 200 events annually and operates from the beautifully restored historic eastbound Milford train station, as well as the Firehouse Gallery at Walnut Beach. Jazz’n Downtown 📅 Saturday, October 3, 2026 📍 Downtown Milford, Connecticut 🎷 Event Information: jazzndowntown.org 🎟️ Tickets: Eventbrite – Jazz’n Downtown: The Ultimate Jazz & Arts Experience 🎨 Milford Arts Council: milfordarts.org ☎️ Information: 203-878-6647 Come for the jazz, explore downtown Milford, discover local artists, enjoy great food and make a full day — and night — of this brand-new Connecticut arts experience.
Stamford, CT: Early Bird pricing ends Sept. 15 at 11:59 PM for WineFest on Bedford, happening Oct. 3 at Latham Park in Stamford Downtown.
Fall is calling! Cooler days, changing leaves, apple picking, cider donuts, country fairs, pumpkin patches and fall festivals are returning throughout Connecticut and the Hudson Valley. One of the best things about living in Fairfield County is how many great fall destinations are within an easy drive. You can stay close to home, head toward the Connecticut shoreline or Litchfield Hills, or cross the New York border for a Hudson Valley fall road trip. Fairfield After Dark has rounded up some of our Hot Picks for Fall 2026 . Grab your sweater and start planning! 🍎 FAIRFIELD COUNTY Blue Jay Orchards — Bethel A local fall favorite for pick-your-own apples, pumpkins, a farm market and those must-have cider donuts. Silverman’s Farm — Easton Apple picking, pumpkins, a country market and animal farm make Silverman’s an easy family fall outing. Beardsley’s Cider Mill & Orchard — Shelton Pick apples and stock up on fresh cider, cider donuts, pies and other bakery favorites. Aki Matsuri Fall Festival — Westport | Sept. 19 Japanese culture takes over Jesup Green with taiko drumming, dancing, martial arts, activities and a marketplace. Westoberfest — Westport | Oct. 3 Downtown Westport celebrates Oktoberfest with local and regional beer, live music and fall fun. NICE Festival — Norwalk | Oct. 3 Oyster Shell Park comes alive with international food, music, dance, arts, crafts and cultural performances. 🍏 NEW HAVEN COUNTY Bishop’s Orchards Fall Festival — Guilford | Through Nov. 1 One of FAD’s biggest fall picks with apple picking, a corn maze, wagon rides, pumpkins, food and seasonal activities. Rose Orchards — North Branford Apples, pumpkins, corn maze, wagon rides, farm market and creamery make this a full fall afternoon. Blue Hills Orchard — Wallingford A traditional Connecticut orchard experience with seasonal apple picking and wagon rides. Guilford Fair — Sept. 18–20 A classic agricultural fair with rides, animals, exhibits, food, crafts and entertainment. Orange Country Fair — Sept. 19–20 Old-fashioned country-fair fun filled with agriculture, food, entertainment and family activities. Seymour Pumpkin Festival — Sept. 20 French Memorial Park fills with arts, crafts, food and family activities celebrating fall. Milford Oktoberfest — Sept. 25–26 Head to Fowler Field for beer, food, music and traditional Oktoberfest festivities. 🍂 LITCHFIELD COUNTY Averill Farm — Washington Depot Pick apples and pears while enjoying one of the most picturesque old-fashioned farm experiences in the Litchfield Hills. March Farm — Bethlehem Pick-your-own fruit, a farm market, bakery, animals, corn maze and weekend hayrides. The Farm — Woodbury | Through Oct. 30 Corn maze, pumpkins, hayrides, sunflowers, music and seasonal farm fun. Harwinton Fair — Oct. 2–4 Pig races, tractors, animals, bluegrass, food and plenty of old-fashioned country-fair traditions. Connecticut Garlic & Harvest Festival — Bethlehem | Oct. 10–11 Garlic, harvest foods, vendors and fall festivities take over the Bethlehem Fairgrounds. 🍎 WESTCHESTER COUNTY, NY Harvest Moon Farm & Orchard — North Salem Apple picking meets fall festival with hayrides, live music, cider donuts, seasonal food and pumpkins. Outhouse Orchards — North Salem Apples, pumpkins, corn maze, hayrides and cider donuts make this another North Salem favorite. Stuart’s Fruit Farm — Granite Springs A traditional apple-picking destination with a farm stand, bakery and weekend hayrides. Wilkens Fruit & Fir Farm — Yorktown Heights Apple picking, farm-market goodies and seasonal treats make Wilkens another Westchester fall tradition. 🍎 PUTNAM COUNTY, NY Salinger’s Orchard — Brewster No pick-your-own here, but definitely worth a stop for locally grown apples, cider donuts, pies and its Farm Market & Bakery. 🍏 DUTCHESS / RENSSELAER COUNTIES, NY Fishkill Farms — Hopewell Junction Apple and pumpkin picking, wagon rides, cider donuts, seasonal food and Treasury Cider make this a great Hudson Valley day trip. Goold Hill Estate – Castleton-on-Hudson Goold Hill Estate is now open, welcoming guests for apple picking, family-friendly farm experiences, live music and events, artisan markets, seasonal treats, locally crafted ciders, and a glimpse at its future Estate wines. Barton Orchards — Poughquag Go big with apple and pumpkin picking, family attractions, food, entertainment and fall festival weekends. Meadowbrook Farm — Wappingers Falls A smaller farm experience for apples, pumpkins, cider donuts and seasonal farm-market shopping. Hudson Valley Wine & Food Festival — Rhinebeck Make it a grown-up fall road trip with regional wines, craft beverages, food and Hudson Valley producers. 🍎🍩 FAD’s Fall Advice: Never Skip the Cider Donuts! Whether you stay close to home in Fairfield County, head north into the Litchfield Hills or cross the border into New York, there’s plenty of fall fun waiting within an easy road trip. Remember: Apple varieties, picking conditions, hours and activities can change throughout the season. Check directly with farms and festivals before heading out, especially when pick-your-own apples are the main reason for your visit. Now grab the family, your friends — or your favorite fall date — and go enjoy autumn! Keep checking FairfieldAfterDark.com for more Fall Happenings, Halloween Events, Fairs, Festivals, Live Music and Things To Do in and around Fairfield County.
September 14–20, 2026 Fall entertainment is kicking into high gear, and Fairfield After Dark has your week covered! From comedy and live music to vineyard happenings, a legendary cultural commentator and artisan shopping, there are plenty of reasons to get out this week. Here are FAD’s Top Picks for September 14–20! 🍷 TUESDAY, SEPTEMBER 15 | AQUILA’S NEST VINEYARDS — NEWTOWN Kick off the week at Aquila’s Nest Vineyards with Whispers From Heaven with Patricia Griffin . Enjoy the vineyard setting while checking out one of the many special experiences happening throughout the week. 👉 GET THE DETAILS & PLAN YOUR VISIT HERE 😂 WEDNESDAY, SEPTEMBER 16 | NEW YORK COMEDY CLUB — STAMFORD Need a midweek laugh? Mike Cannon hits the stage at New York Comedy Club Stamford Wednesday at 7 PM . 👉 GRAB YOUR TICKETS HERE 🍷 WEDNESDAY, SEPTEMBER 16 | AQUILA’S NEST VINEYARDS — NEWTOWN Put on those boots and head to Newtown! Country Line Dancing is on the schedule Wednesday at Aquila’s Nest Vineyards. 👉 GET THE DETAILS HERE 💕 WEDNESDAY, SEPTEMBER 16 | ODEEN’S at Oak Hills - Norwalk Meet local singles ages 25–39 face-to-face at ODEEN’S Oak Hills for a fun, low-pressure evening of speed dating, guided conversations, and the chance to make a real connection. 👉 Tickets are limited GRAB YOUR TICKETS HERE 🎹 THURSDAY, SEPTEMBER 17 | THE BILLY JOEL LEGACY — THE PALACE STAMFORD The music of the Piano Man comes alive when The Billy Joel Legacy: A Tribute Experience takes the stage at The Palace Stamford Thursday at 7:30 PM . Billy Joel fans, this one's for you! 👉 GRAB YOUR TICKETS HERE 🍷 THURSDAY, SEPTEMBER 17 | AQUILA’S NEST VINEYARDS — NEWTOWN Aquila’s Nest keeps the week going with several Thursday experiences, including Pilates, Plant Bingo and special workshops . 👉 GET THE DETAILS HERE 🎤 FRIDAY, SEPTEMBER 18 | FRAN LEBOWITZ — EDMOND TOWN HALL, NEWTOWN Known for her razor-sharp wit, unapologetic opinions and hilarious observations on modern life, Fran Lebowitz comes to Edmond Town Hall Friday at 8 PM . Doors open at 7 PM. 👉 GRAB YOUR TICKETS HERE 🎤 FRIDAY, SEPTEMBER 18 | SIMPLY THE BEST — THE PALACE STAMFORD Get ready for the music of Tina Turner! Simply The Best: A Tribute to the Music of Tina Turner takes over The Palace Stamford Friday at 8 PM . 👉 GRAB YOUR TICKETS HERE 😂 FRIDAY, SEPTEMBER 18 | CAITLIN PELUFFO — NEW YORK COMEDY CLUB STAMFORD Start your weekend laughing with Caitlin Peluffo , performing two shows Friday night at 7 PM and 9:30 PM . 👉 GRAB YOUR TICKETS HERE 🦙🍷 FRIDAY, SEPTEMBER 18 | AQUILA’S NEST VINEYARDS — NEWTOWN Friday brings even more fun to Aquila’s Nest with Llamas & Llibations and Cruise Night . 👉 GET THE DETAILS HERE 🛍️ SATURDAY, SEPTEMBER 19 | POP SHOP MARKET — DARIEN COMMONS Shop small and discover something different when PopShop Market returns to Darien Commons Saturday from 11 AM–5 PM . Explore a curated collection of independent makers and small businesses offering apparel, jewelry, home décor, self-care products, gifts and plenty of one-of-a-kind finds. 👉 GET ALL THE DETAILS HERE 😂 SATURDAY, SEPTEMBER 19 | NEW YORK COMEDY CLUB — STAMFORD Saturday starts early with Early Bird Comedy at 4:30 PM , followed by another performance from Caitlin Peluffo at 7 PM . 👉 GRAB YOUR TICKETS HERE 🍷🎸 SATURDAY, SEPTEMBER 19 | THE 80s ROCK EXPERIENCE — AQUILA’S NEST VINEYARDS Turn back the clock at Aquila’s Nest with The 80s Rock Experience Tribute Show , happening Saturday from 6–9 PM . 👉 GRAB YOUR TICKETS & GET THE DETAILS HERE 🎹 SATURDAY, SEPTEMBER 19 | THE MIGHTY FRANKLIN BROTHERS — THE PALACE DANBURY Steely Dan fans, this one's for you! The Mighty Franklin Brothers take over The Palace Danbury Saturday at 7:30 PM . Led by brothers Jay and Carl Franklin and backed by a powerhouse lineup of musicians and horns, the band brings the sophisticated arrangements, soulful vocals and unmistakable sound of Steely Dan to the stage. 👉 GRAB YOUR TICKETS HERE 🎬🎶 SATURDAY, SEPTEMBER 19 | LABYRINTH IN CONCERT — THE PALACE STAMFORD Celebrate 40 years of a cult classic with Jim Henson’s Labyrinth: In Concert — 40th Anniversary at The Palace Stamford Saturday at 7:30 PM. 👉 GRAB YOUR TICKETS HERE 🎶 SUNDAY, SEPTEMBER 20 | GREEN EYED LADY — ODEEN’S OAK HILLS, NORWALK Wrap up the weekend with dinner and live music! Green Eyed Lady performs at Odeen’s Oak Hills Sunday from 4–7 PM . 👉 Make a Reservation here! ⭐ GET OUT & HAVE SOME FUN! From Newtown to Stamford, Darien, Danbury, Ridgefield, New Canaan and Norwalk , there’s plenty happening this week. These are just a few of FAD’s Top Picks — grab your tickets, make those reservations and start planning your week early! 🎶 😂 🍷 🛍️ 🎭 Get Out. Have Fun. Live Local. See even more concerts, comedy, festivals, fairs, fall happenings and Things To Do in and around Fairfield County at FairfieldAfterDark.com.
Milford, CT: Downtown Milford will come alive with the sounds of jazz on Saturday, October 3, 2026 , as the Milford Arts Council presents the inaugural Jazz’n Downtown , a new immersive celebration combining live music, local art, dining and the charm of one of Connecticut’s favorite shoreline downtowns. Presented with lead Presenting Sponsor Coastal Bridge Advisors , Jazz’n Downtown is designed to be explored at your own pace. Visitors can arrive by train, car, boat, bike or foot and spend the day strolling Milford’s historic neighborhoods, waterways, boutiques, restaurants and artisan displays — all while live jazz provides the soundtrack. Jazz Throughout Downtown Milford Award-winning jazz performers will take the stage at three outdoor venues , including locations along Milford’s scenic waterfront. The music continues throughout the downtown experience, with solo and duo jazz performers appearing at participating restaurants during brunch, lunch and dinner. It’s more than a traditional music festival. Jazz’n Downtown brings music, art, food and community together throughout the heart of Milford, allowing guests to create their own experience and discover something new around every corner. An Evening Celebrating Ella & Louis The celebration continues that evening at Parsons Veterans’ Memorial Hall with a special tribute concert honoring two of jazz music’s most legendary performers, Ella Fitzgerald and Louis Armstrong . The evening concert requires a separate ticket, while VIP packages offer an enhanced Jazz’n Downtown experience with reserved seating areas, an early reservation window for brunch, lunch and dinner, parking and reserved seating for the evening concert. About the Milford Arts Council Founded in 1972, the Milford Arts Council (MAC) is a nonprofit organization dedicated to connecting and enriching the community through music, theater, visual arts, dance, film and creative expression. MAC presents more than 200 events annually and operates from the beautifully restored historic eastbound Milford train station, as well as the Firehouse Gallery at Walnut Beach. Jazz’n Downtown 📅 Saturday, October 3, 2026 📍 Downtown Milford, Connecticut 🎷 Event Information: jazzndowntown.org 🎟️ Tickets: Eventbrite – Jazz’n Downtown: The Ultimate Jazz & Arts Experience 🎨 Milford Arts Council: milfordarts.org ☎️ Information: 203-878-6647 Come for the jazz, explore downtown Milford, discover local artists, enjoy great food and make a full day — and night — of this brand-new Connecticut arts experience.
Stamford, CT: Early Bird pricing ends Sept. 15 at 11:59 PM for WineFest on Bedford, happening Oct. 3 at Latham Park in Stamford Downtown.
Fall is calling! Cooler days, changing leaves, apple picking, cider donuts, country fairs, pumpkin patches and fall festivals are returning throughout Connecticut and the Hudson Valley. One of the best things about living in Fairfield County is how many great fall destinations are within an easy drive. You can stay close to home, head toward the Connecticut shoreline or Litchfield Hills, or cross the New York border for a Hudson Valley fall road trip. Fairfield After Dark has rounded up some of our Hot Picks for Fall 2026 . Grab your sweater and start planning! 🍎 FAIRFIELD COUNTY Blue Jay Orchards — Bethel A local fall favorite for pick-your-own apples, pumpkins, a farm market and those must-have cider donuts. Silverman’s Farm — Easton Apple picking, pumpkins, a country market and animal farm make Silverman’s an easy family fall outing. Beardsley’s Cider Mill & Orchard — Shelton Pick apples and stock up on fresh cider, cider donuts, pies and other bakery favorites. Aki Matsuri Fall Festival — Westport | Sept. 19 Japanese culture takes over Jesup Green with taiko drumming, dancing, martial arts, activities and a marketplace. Westoberfest — Westport | Oct. 3 Downtown Westport celebrates Oktoberfest with local and regional beer, live music and fall fun. NICE Festival — Norwalk | Oct. 3 Oyster Shell Park comes alive with international food, music, dance, arts, crafts and cultural performances. 🍏 NEW HAVEN COUNTY Bishop’s Orchards Fall Festival — Guilford | Through Nov. 1 One of FAD’s biggest fall picks with apple picking, a corn maze, wagon rides, pumpkins, food and seasonal activities. Rose Orchards — North Branford Apples, pumpkins, corn maze, wagon rides, farm market and creamery make this a full fall afternoon. Blue Hills Orchard — Wallingford A traditional Connecticut orchard experience with seasonal apple picking and wagon rides. Guilford Fair — Sept. 18–20 A classic agricultural fair with rides, animals, exhibits, food, crafts and entertainment. Orange Country Fair — Sept. 19–20 Old-fashioned country-fair fun filled with agriculture, food, entertainment and family activities. Seymour Pumpkin Festival — Sept. 20 French Memorial Park fills with arts, crafts, food and family activities celebrating fall. Milford Oktoberfest — Sept. 25–26 Head to Fowler Field for beer, food, music and traditional Oktoberfest festivities. 🍂 LITCHFIELD COUNTY Averill Farm — Washington Depot Pick apples and pears while enjoying one of the most picturesque old-fashioned farm experiences in the Litchfield Hills. March Farm — Bethlehem Pick-your-own fruit, a farm market, bakery, animals, corn maze and weekend hayrides. The Farm — Woodbury | Through Oct. 30 Corn maze, pumpkins, hayrides, sunflowers, music and seasonal farm fun. Harwinton Fair — Oct. 2–4 Pig races, tractors, animals, bluegrass, food and plenty of old-fashioned country-fair traditions. Connecticut Garlic & Harvest Festival — Bethlehem | Oct. 10–11 Garlic, harvest foods, vendors and fall festivities take over the Bethlehem Fairgrounds. 🍎 WESTCHESTER COUNTY, NY Harvest Moon Farm & Orchard — North Salem Apple picking meets fall festival with hayrides, live music, cider donuts, seasonal food and pumpkins. Outhouse Orchards — North Salem Apples, pumpkins, corn maze, hayrides and cider donuts make this another North Salem favorite. Stuart’s Fruit Farm — Granite Springs A traditional apple-picking destination with a farm stand, bakery and weekend hayrides. Wilkens Fruit & Fir Farm — Yorktown Heights Apple picking, farm-market goodies and seasonal treats make Wilkens another Westchester fall tradition. 🍎 PUTNAM COUNTY, NY Salinger’s Orchard — Brewster No pick-your-own here, but definitely worth a stop for locally grown apples, cider donuts, pies and its Farm Market & Bakery. 🍏 DUTCHESS / RENSSELAER COUNTIES, NY Fishkill Farms — Hopewell Junction Apple and pumpkin picking, wagon rides, cider donuts, seasonal food and Treasury Cider make this a great Hudson Valley day trip. Goold Hill Estate – Castleton-on-Hudson Goold Hill Estate is now open, welcoming guests for apple picking, family-friendly farm experiences, live music and events, artisan markets, seasonal treats, locally crafted ciders, and a glimpse at its future Estate wines. Barton Orchards — Poughquag Go big with apple and pumpkin picking, family attractions, food, entertainment and fall festival weekends. Meadowbrook Farm — Wappingers Falls A smaller farm experience for apples, pumpkins, cider donuts and seasonal farm-market shopping. Hudson Valley Wine & Food Festival — Rhinebeck Make it a grown-up fall road trip with regional wines, craft beverages, food and Hudson Valley producers. 🍎🍩 FAD’s Fall Advice: Never Skip the Cider Donuts! Whether you stay close to home in Fairfield County, head north into the Litchfield Hills or cross the border into New York, there’s plenty of fall fun waiting within an easy road trip. Remember: Apple varieties, picking conditions, hours and activities can change throughout the season. Check directly with farms and festivals before heading out, especially when pick-your-own apples are the main reason for your visit. Now grab the family, your friends — or your favorite fall date — and go enjoy autumn! Keep checking FairfieldAfterDark.com for more Fall Happenings, Halloween Events, Fairs, Festivals, Live Music and Things To Do in and around Fairfield County.
September 14–20, 2026 Fall entertainment is kicking into high gear, and Fairfield After Dark has your week covered! From comedy and live music to vineyard happenings, a legendary cultural commentator and artisan shopping, there are plenty of reasons to get out this week. Here are FAD’s Top Picks for September 14–20! 🍷 TUESDAY, SEPTEMBER 15 | AQUILA’S NEST VINEYARDS — NEWTOWN Kick off the week at Aquila’s Nest Vineyards with Whispers From Heaven with Patricia Griffin . Enjoy the vineyard setting while checking out one of the many special experiences happening throughout the week. 👉 GET THE DETAILS & PLAN YOUR VISIT HERE 😂 WEDNESDAY, SEPTEMBER 16 | NEW YORK COMEDY CLUB — STAMFORD Need a midweek laugh? Mike Cannon hits the stage at New York Comedy Club Stamford Wednesday at 7 PM . 👉 GRAB YOUR TICKETS HERE 🍷 WEDNESDAY, SEPTEMBER 16 | AQUILA’S NEST VINEYARDS — NEWTOWN Put on those boots and head to Newtown! Country Line Dancing is on the schedule Wednesday at Aquila’s Nest Vineyards. 👉 GET THE DETAILS HERE 💕 WEDNESDAY, SEPTEMBER 16 | ODEEN’S at Oak Hills - Norwalk Meet local singles ages 25–39 face-to-face at ODEEN’S Oak Hills for a fun, low-pressure evening of speed dating, guided conversations, and the chance to make a real connection. 👉 Tickets are limited GRAB YOUR TICKETS HERE 🎹 THURSDAY, SEPTEMBER 17 | THE BILLY JOEL LEGACY — THE PALACE STAMFORD The music of the Piano Man comes alive when The Billy Joel Legacy: A Tribute Experience takes the stage at The Palace Stamford Thursday at 7:30 PM . Billy Joel fans, this one's for you! 👉 GRAB YOUR TICKETS HERE 🍷 THURSDAY, SEPTEMBER 17 | AQUILA’S NEST VINEYARDS — NEWTOWN Aquila’s Nest keeps the week going with several Thursday experiences, including Pilates, Plant Bingo and special workshops . 👉 GET THE DETAILS HERE 🎤 FRIDAY, SEPTEMBER 18 | FRAN LEBOWITZ — EDMOND TOWN HALL, NEWTOWN Known for her razor-sharp wit, unapologetic opinions and hilarious observations on modern life, Fran Lebowitz comes to Edmond Town Hall Friday at 8 PM . Doors open at 7 PM. 👉 GRAB YOUR TICKETS HERE 🎤 FRIDAY, SEPTEMBER 18 | SIMPLY THE BEST — THE PALACE STAMFORD Get ready for the music of Tina Turner! Simply The Best: A Tribute to the Music of Tina Turner takes over The Palace Stamford Friday at 8 PM . 👉 GRAB YOUR TICKETS HERE 😂 FRIDAY, SEPTEMBER 18 | CAITLIN PELUFFO — NEW YORK COMEDY CLUB STAMFORD Start your weekend laughing with Caitlin Peluffo , performing two shows Friday night at 7 PM and 9:30 PM . 👉 GRAB YOUR TICKETS HERE 🦙🍷 FRIDAY, SEPTEMBER 18 | AQUILA’S NEST VINEYARDS — NEWTOWN Friday brings even more fun to Aquila’s Nest with Llamas & Llibations and Cruise Night . 👉 GET THE DETAILS HERE 🛍️ SATURDAY, SEPTEMBER 19 | POP SHOP MARKET — DARIEN COMMONS Shop small and discover something different when PopShop Market returns to Darien Commons Saturday from 11 AM–5 PM . Explore a curated collection of independent makers and small businesses offering apparel, jewelry, home décor, self-care products, gifts and plenty of one-of-a-kind finds. 👉 GET ALL THE DETAILS HERE 😂 SATURDAY, SEPTEMBER 19 | NEW YORK COMEDY CLUB — STAMFORD Saturday starts early with Early Bird Comedy at 4:30 PM , followed by another performance from Caitlin Peluffo at 7 PM . 👉 GRAB YOUR TICKETS HERE 🍷🎸 SATURDAY, SEPTEMBER 19 | THE 80s ROCK EXPERIENCE — AQUILA’S NEST VINEYARDS Turn back the clock at Aquila’s Nest with The 80s Rock Experience Tribute Show , happening Saturday from 6–9 PM . 👉 GRAB YOUR TICKETS & GET THE DETAILS HERE 🎹 SATURDAY, SEPTEMBER 19 | THE MIGHTY FRANKLIN BROTHERS — THE PALACE DANBURY Steely Dan fans, this one's for you! The Mighty Franklin Brothers take over The Palace Danbury Saturday at 7:30 PM . Led by brothers Jay and Carl Franklin and backed by a powerhouse lineup of musicians and horns, the band brings the sophisticated arrangements, soulful vocals and unmistakable sound of Steely Dan to the stage. 👉 GRAB YOUR TICKETS HERE 🎬🎶 SATURDAY, SEPTEMBER 19 | LABYRINTH IN CONCERT — THE PALACE STAMFORD Celebrate 40 years of a cult classic with Jim Henson’s Labyrinth: In Concert — 40th Anniversary at The Palace Stamford Saturday at 7:30 PM. 👉 GRAB YOUR TICKETS HERE 🎶 SUNDAY, SEPTEMBER 20 | GREEN EYED LADY — ODEEN’S OAK HILLS, NORWALK Wrap up the weekend with dinner and live music! Green Eyed Lady performs at Odeen’s Oak Hills Sunday from 4–7 PM . 👉 Make a Reservation here! ⭐ GET OUT & HAVE SOME FUN! From Newtown to Stamford, Darien, Danbury, Ridgefield, New Canaan and Norwalk , there’s plenty happening this week. These are just a few of FAD’s Top Picks — grab your tickets, make those reservations and start planning your week early! 🎶 😂 🍷 🛍️ 🎭 Get Out. Have Fun. Live Local. See even more concerts, comedy, festivals, fairs, fall happenings and Things To Do in and around Fairfield County at FairfieldAfterDark.com.
Milford, CT: Downtown Milford will come alive with the sounds of jazz on Saturday, October 3, 2026 , as the Milford Arts Council presents the inaugural Jazz’n Downtown , a new immersive celebration combining live music, local art, dining and the charm of one of Connecticut’s favorite shoreline downtowns. Presented with lead Presenting Sponsor Coastal Bridge Advisors , Jazz’n Downtown is designed to be explored at your own pace. Visitors can arrive by train, car, boat, bike or foot and spend the day strolling Milford’s historic neighborhoods, waterways, boutiques, restaurants and artisan displays — all while live jazz provides the soundtrack. Jazz Throughout Downtown Milford Award-winning jazz performers will take the stage at three outdoor venues , including locations along Milford’s scenic waterfront. The music continues throughout the downtown experience, with solo and duo jazz performers appearing at participating restaurants during brunch, lunch and dinner. It’s more than a traditional music festival. Jazz’n Downtown brings music, art, food and community together throughout the heart of Milford, allowing guests to create their own experience and discover something new around every corner. An Evening Celebrating Ella & Louis The celebration continues that evening at Parsons Veterans’ Memorial Hall with a special tribute concert honoring two of jazz music’s most legendary performers, Ella Fitzgerald and Louis Armstrong . The evening concert requires a separate ticket, while VIP packages offer an enhanced Jazz’n Downtown experience with reserved seating areas, an early reservation window for brunch, lunch and dinner, parking and reserved seating for the evening concert. About the Milford Arts Council Founded in 1972, the Milford Arts Council (MAC) is a nonprofit organization dedicated to connecting and enriching the community through music, theater, visual arts, dance, film and creative expression. MAC presents more than 200 events annually and operates from the beautifully restored historic eastbound Milford train station, as well as the Firehouse Gallery at Walnut Beach. Jazz’n Downtown 📅 Saturday, October 3, 2026 📍 Downtown Milford, Connecticut 🎷 Event Information: jazzndowntown.org 🎟️ Tickets: Eventbrite – Jazz’n Downtown: The Ultimate Jazz & Arts Experience 🎨 Milford Arts Council: milfordarts.org ☎️ Information: 203-878-6647 Come for the jazz, explore downtown Milford, discover local artists, enjoy great food and make a full day — and night — of this brand-new Connecticut arts experience.
