There’s something about fall in Connecticut that just makes you want to grab a sweater, jump in the car and head to a farm. Pumpkin patches are opening, cider donuts are calling, corn mazes are ready to be conquered, and our Fairfield County countryside is about to put on its annual show of spectacular fall color. Whether you're searching for the perfect pumpkin to carve, planning a family outing with the kids, looking for a fall date-day destination or simply want an excuse to get outside and enjoy autumn, Fairfield After Dark has rounded up some of our favorite pumpkin-picking destinations in and around Fairfield County. And we’re not stopping at the county line! We’ve included farms in neighboring New Haven and Litchfield Counties, plus some great destinations just across the New York border in Westchester, Putnam and nearby Dutchess County. FAIRFIELD COUNTY PUMPKIN PATCHES BETHEL Blue Jay Orchards - 125 Plumtrees Road, Bethel A Fairfield County fall classic! Blue Jay Orchards combines its beautiful orchard setting with a seasonal pumpkin patch, farm market and bakery. The 2026 pumpkin patch opened September 12 with pumpkins ranging from decorative minis and specialty varieties to jumbo jack-o'-lantern candidates. Be sure to make time for cider and those famous cider donuts before heading home. EASTON Silverman's Farm - 451 Sport Hill Road, Easton Silverman’s has been part of the Easton landscape for generations and remains one of Fairfield County’s quintessential fall destinations. Stop for pumpkins and fall decorations, visit the country market for pies, cider and seasonal goodies, and make some time for the farm’s popular Animal Farm. NEWTOWN Castle Hill Farm - Sugar Lane, Newtown If you want the full pumpkin-picking experience, Castle Hill deserves a spot on your fall bucket list. The family farm features a four-acre pick-your-own pumpkin patch with dozens of varieties of pumpkins, gourds and squash, along with its popular corn maze and hayrides. It’s one of those places where pumpkin picking can easily turn into an entire fall afternoon. REDDING Warrup’s Farm - 11 John Read Road, Redding For those who prefer a smaller, old-fashioned farm experience, Warrup’s is a wonderful Redding tradition. The working family farm has long been associated with seasonal produce and fall pumpkin activities and offers a decidedly more rustic alternative to some of the larger fall attractions. SHELTON Pumpkinseed Hill Farm of Jones Family Farms 120 Beardsley Road, Shelton One of the biggest names in Connecticut pumpkin picking, Jones Family Farms turns Pumpkinseed Hill into a fall destination each year. Search the fields for pumpkins in all shapes, colors and sizes, explore the farm, tackle the mini corn maze and add a tractor-drawn hayride to your visit. Reservations are encouraged for the Pumpkinseed Hill Exploration, particularly on busy weekends. Wells Hollow Farms - 656 Bridgeport Avenue, Shelton Another Shelton option for families looking to make an afternoon of it. Wells Hollow offers a festive farm atmosphere with pumpkins, seasonal decorations, a corn maze, animals and plenty of opportunities to enjoy a classic New England fall day. STAMFORD St. John's Luthern Church – 884 Newfield Avenue, Stamford The St. John’s Lutheran Church Pumpkin Patch is an annual October tradition and mission fundraiser featuring hundreds of pumpkins for sale throughout the month. Best of all, proceeds from every pumpkin sold are donated to support those in need. TRUMBULL Plasko's Farm Creamery & Cafe - 670 Daniels Farm Road, Trumbull A longtime Trumbull farm and a fun stop during fall. Plasko’s combines its farm setting with a bakery, café and homemade ice cream, making it an easy addition to a Fairfield County fall drive — especially when cider donuts and ice cream are part of the plan. JUST OVER THE FAIRFIELD COUNTY LINE Some of Connecticut's best pumpkin-picking destinations are only a short drive beyond Fairfield County. These New Haven and Litchfield County farms are particularly convenient for residents of northern and eastern Fairfield County. NEW HAVEN COUNTY BETHANY Clover Nook Farm - 50 Fairwood Road, Bethany This historic family farm dates back generations and offers a traditional farm-market experience. During fall, pumpkins join the farm’s lineup of seasonal produce, flowers, corn stalks, mums and other harvest favorites. Connecticut tourism resources also identify Clover Nook as a pick-your-own pumpkin destination. ORANGE Treat Farm 361 Old Tavern Road, Orange Treat Farm is a great choice for families who like a less commercial farm experience. In addition to seasonal farm offerings, its corn maze has become a fall attraction of its own. It’s an easy trip from lower Fairfield County and the Valley. OXFORD Belinsky Farm - 124 Moose Hill Road, Oxford Right above the Fairfield County line, Belinsky Farm is a terrific option for residents of Shelton, Monroe and Newtown. This smaller family farm offers an old-school farm atmosphere with seasonal pick-your-own crops and fall favorites including pumpkins, gourds and squash. LITCHFIELD COUNTY — WORTH THE SHORT DRIVE NORTH BETHLEHEM March Farm - 160 Munger Lane, Bethlehem This one deserves a fall road trip. March Farm's Hilltop offers beautiful Litchfield County views along with pick-your-own apples and pumpkins, a corn maze, hayrides, food and seasonal activities. Pick-your-own pumpkins generally begins in late September or early October and continues through October. Weekend visits can also include rotating food vendors and live music. WOODBURY Logue Farms, Inc. - Woodbury Looking for a classic country pumpkin-picking experience? Logue Farms is known for its seasonal pumpkin patch and hayride experience. It’s a particularly convenient Litchfield County destination from Southbury, Newtown and northern Fairfield County. LITCHFIELD Bunnell Farm - 498 Maple Street, Litchfield Make a fall foliage drive out of this one. Bunnell Farm's pumpkin season is typically centered around weekends and combines a traditional farm setting with some beautiful Litchfield County scenery. Fox and the Buck Farm, Inc. - 280 Northfield Road, Litchfield If unusual pumpkins are more your style, put Fox and the Buck on your radar. The seasonal family farm specializes in flowers and heirloom pumpkins — perfect for anyone searching for something a little different for the front porch. PUMPKIN PICKING JUST ACROSS THE NEW YORK BORDER Fairfield County residents shouldn't forget about our neighbors to the west. Northern Westchester and Putnam County are practically an extension of our fall playground, and several farms are an easy drive from Greenwich, Stamford, New Canaan, Ridgefield, Danbury and surrounding towns. NORTH SALEM, WESTCHESTER COUNTY Outhouse Orchards - 139 Hardscrabble Road, North Salem If you're looking for a full-scale fall festival, this is one to know. Outhouse Orchards' 2026 Fall Festival runs from August 30 through November 1 and includes a pumpkin patch, apple picking, corn maze, hayrides, photo opportunities, family attractions, farm market, food and seasonal treats. Admission is ticketed during the festival, so check ahead before heading across the border. Harvest Moon Farm & Orchard - 130 Hardscrabble Road, North Salem Practically next door to Outhouse Orchards, Harvest Moon is another popular Westchester fall destination. Expect the combination of orchard scenery, seasonal pumpkin experiences, family activities, food, cider and plenty of fall photo opportunities. GRANITE SPRINGS / SOMERS, WESTCHESTER COUNTY Stuarts Farm - 62 Granite Springs Road, Granite Springs If the giant fall-festival atmosphere isn't your thing, Stuart's is worth considering. This longtime family farm offers a more traditional Hudson Valley orchard experience with seasonal pumpkin picking, apples, a farm stand, bakery treats and a relaxed country setting. BREWSTER, PUTNAM COUNTY Salinger's Orchard - 230 Guinea Road, Brewster Salinger's is an easy ride from the Danbury and Ridgefield areas and a great stop for anyone who loves the farm-market side of fall. The longtime family orchard is especially known for its bakery, pies, cider donuts and seasonal produce. Think of this one more as a fall farm-market destination than a major pick-your-own pumpkin attraction. PAWLING, DUTCHESS COUNTY Dykeman Farm - 31 Dykeman Lane, Pawling Just beyond Putnam County, Dykeman Farm is worth adding to the list for northern Fairfield County residents. The fourth-generation family farm is known for a genuine pick-your-own pumpkin experience with a huge variety of pumpkins and a refreshingly traditional farm atmosphere. 🎃 MAKE A DAY OF IT! One of the best things about living in Fairfield County is that you don't have to travel very far to experience a picture-perfect New England fall. Start close to home in Bethel, Easton, Newtown, Redding, Shelton, Westport, Ridgefield or Trumbull — or turn pumpkin picking into a fall road trip through the rolling hills of Litchfield County or across the border into Westchester and the Hudson Valley. Pack the kids. Grab the camera. Bring home a pumpkin — or five. And whatever you do, don't forget the cider donuts! FAD TIP: Pumpkin availability, hayrides, corn mazes and special activities can change because of weather and crop conditions. Always check directly with the farm before heading out, particularly later in October. Happy Pumpkin Picking from Fairfield After Dark! 🎃🍎🍂