Fall Activities Near Fairfield County

Your Guide to the Best Fall October Activities Near Fairfield County, Connecticut

October in Fairfield County, Connecticut is one of the most magical times of the year, when the air gets crisp, the leaves turn golden, and pumpkin-spiced everything takes over! I really have been meaning to do this post for the longest time. There is always something fall-ish to do in Connecticut in the month of October. Whether you’re looking for festive pumpkin patches, family-friendly farms, or spooky Halloween events, there’s no shortage of fall activities to celebrate the season. Here’s a roundup of the best fall activities near Fairfield County Connecticut this October!

Before we jump to the post, check out these other Fall Activities:

• Apple Picking Season
• Pumpkin Patch with Older Kids
• New England Fall Activities
• Fall To-Do List

Visit Pumpkin Patches and Farms

October isn’t complete without a trip to the pumpkin patch, and Fairfield County has some of the best spots to pick out the perfect pumpkin and enjoy fall on the farm.

• Silverman’s Farm (Easton, CT): This beloved farm offers a fun pumpkin patch where you can pick your own pumpkins, a scenic tractor-pulled hayride to their apple orchard, and a petting zoo the kids will love. Be sure to check out their farm market, which is stocked with fresh apples, apple cider, homemade pies, and all the fall goodies you can imagine! Their apple cider donuts are some of the best! While you are there, pick-your-own apples. See more of our Silverman’s Farm adventure.
• Jones Family Farms (Shelton, CT): Known for its stunning fall foliage, Jones Family Farms is a must-visit in October, and one of our favorite fall spots. Take a ride on the Harvest Experience Hayride and wander through the Pumpkin Valley to find your perfect pumpkin. They have pumpkins still on the vine in their pumpkin field–our favorite way to pick our pumpkins. Their corn maze is small, but still so fun! We also love their sunflower and zinnia field for pretty photo ops.
• Blue Jay Orchards (Bethel, CT): Blue Jay Orchards is full of fun fall days with gorgeous landscapes of apple trees and pumpkins. They have fairly large farmer’s market with homemade goodies, local jams and sauces and apples.
• Lyman Orchards (Middlefield, CT): A little further from Fairfield County, this 275-year-old farm is definitely worth the trip. The landscape is so beautiful with changing of fall leaves, and the orchard is huge! Enjoy a crisp day in the orchards picking apples, one of Connecticut’s top apple orchards and nationally rated. They also have pumpkins patch with pumpkins still on the vine. Lyman is also known for their 3-acre corn maze! It’s huge and so fun to get lost in. Each year they change the design of the maze with a fun artwork. Definitely worth the fun. They have a beautiful selection of pumpkins, gourds, and fall decorations in their market. And warm up with their fresh apple cider donuts–simply the best and one of our favorite.

Explore Nature Centers and Scenic Spots

Fall is the perfect time to get outside and enjoy Connecticut’s natural beauty. The brilliant colors of the trees, cool weather, and peaceful trails make exploring nature centers and parks a refreshing way to embrace autumn.

• The Stamford Museum & Nature Center (Stamford, CT): This family-friendly spot features nature trails, a working farm, and a seasonal exhibit called “Heckscher Farm Harvest Festival.” Kids will love seeing the animals and learning about sustainable farming, while adults can admire the foliage on scenic walks. They also offer fun events like their Fall Family Fest Sunday Harvest Festival, with apple slingshots and pumpkin decorating. And also trick- or-treat in Heckscher Farm for their members.
• Mather’s Homestead (Darien, CT): A beautiful historical landmark with home and property, Mather’s Homestead is open to the public and has numerous Fall activities. Our favorite one is the Fall Harvest Festival with apple bobbing, hay rides, crafts, games, face painting and a visit from George Washington and his horse.
• Audubon Greenwich (Greenwich, CT): If you’re looking for a tranquil escape to enjoy the fall foliage, Audubon Greenwich is the place to go. With over 700 acres of woodlands, wetlands, and meadows, it’s an excellent spot for hiking and bird-watching.
• Weir Farm National Historical Park (Wilton, CT): For art and nature lovers, Weir Farm is a peaceful haven offering beautiful landscapes and a peek into the world of American Impressionist art. In the fall, the grounds are a palette of orange, red, and gold—a perfect backdrop for a relaxing walk and some artistic inspiration.
• Muscoot Farm (Katonah, NY): A little farther from Fairfield County, but definitely worth the drive to see the fall leaves and enjoy the farm life. Muscoot Farm is a working farm and has so many fun animal interaction activities for children. They also have a pumpkin picking weekend. And bookmark for their maple sugar program in the winter months.
• Kent Falls (Kent, CT): If you want to see fall leaves and enjoy a hike in nature, Kent Falls is a beautiful spot just outside Fairfield County. The red covered bridge makes the scenery picturesque. Grab lunch in the charming town of Kent!

Historic Hudson Valley: Fall and Halloween Festivities

Just a short drive from Fairfield County, the Hudson Valley is steeped in Halloween history at Sleepy Hollow and offers some of the most memorable fall experiences in the region. From farm-to-table dining at Stone Barns to Halloween thrills at the Great Jack O’Lantern Blaze, here’s what you can enjoy across the New York border.

• Stone Barns Center for Food & Agriculture (Pocantico Hills, NY): For those interested in sustainable farming and fine dining, a visit to Stone Barns is a must. This working farm and educational center offers tours where you can learn about regenerative agriculture while admiring the fall foliage. Afterward, enjoy an unforgettable meal at the world-renowned Blue Hill restaurant, which sources ingredients straight from the farm.
• Rockefeller State Park Preserve (Pleasantville, NY): This stunning park is perfect for a fall hike or horseback ride. The park’s scenic carriage roads, which wind through forests and open meadows, offer some of the best leaf-peeping in the area. The views of the rolling hills and nearby Pocantico River make it a peaceful retreat during autumn. You can also see visit of the Hudson River.
• Hudson River Valley Historical Mansions (Hudson River Valley, NY): There are numerous Rockefeller and Vanderbilt estates along the Hudson River. Take a beautiful fall afternoon to go and explore these historical country homes. The backdrop of the Hudson River is gorgeous along with the colorful fall leaves.
• The Great Jack O’Lantern Blaze (Croton-on-Hudson, NY): A must-see fall spectacle, the Great Jack O’Lantern Blaze features over 7,000 hand-carved, illuminated pumpkins arranged into jaw-dropping displays. From towering dinosaurs to spooky tunnels of glowing pumpkins, this family-friendly event is sure to enchant visitors of all ages. Be sure to book tickets early, as this popular event sells out quickly.
• Sleepy Hollow Haunted Attractions (Sleepy Hollow, NY): For those seeking some Halloween thrills, head to Sleepy Hollow, the famous town known for Washington Irving’s The Legend of Sleepy Hollow. Visiting Sleepy Hollow is one of our FAVORITE Halloween activities! This historic village goes all out for Halloween, offering lantern tours of the Sleepy Hollow Cemetery, haunted hayrides, and tales of the Headless Horseman. It’s the perfect destination for anyone looking for a spooky (yet historic) experience. Make sure to also check out Historic Hudson Valley to see the many Halloween Events that they offer. We usually book one of their Halloween activities and they do not disappoint.

Spooky Halloween Events Near Fairfield County

October is Halloween season, and Fairfield County offers a mix of spooky, fun, and family-friendly activities to celebrate!

• Legends of Fear (Shelton, CT): If you’re in the mood for a real fright, Legends of Fear is an award-winning haunted attraction set on Fairview Tree Farm. Brace yourself for a hair-raising walk through the Haunted Forest and the Hallow, or take a spooky hayride through the farm’s eerie woods.
• Boo at the Zoo (Bridgeport, CT): The Beardsley Zoo offers a family-friendly Halloween event featuring trick-or-treating, scavenger hunts, and costume contests. It’s a fun way to enjoy Halloween with younger kids in a safe and festive environment.
• Halloween on the Green (Fairfield, CT): This family-friendly event is held on the Fairfield Museum Commons and includes trick-or-treating, a parade, a haunted house, and tons of games and activities for kids. It’s the perfect way to get into the spirit of Halloween without being too spooky for little ones.
• Ambler Farm Fright Night (Wilton, CT): Creepy sights and mysterious sounds abound when the moon rises at Ambler Farm. This is not-too frightful evening of spooky stories, a haunted hayride, and some sweet treats for children in grades 3rd-5th.

Whether you’re looking for classic pumpkin patch outings, scenic fall hikes, or spooky Halloween thrills, Fall activities near Fairfield County and its surrounding areas are bursting with autumn adventures for every age and interest. So grab your coziest sweater, sip some hot apple cider, and make the most of October in one of Connecticut’s most beautiful regions!