There is something magical about fall in New England. Having been born and raised in Connecticut, I absolutely love this time of year: the warm days, cool mornings and nights, and all the fun, festive activities that aren’t in 90-degree heat. I am a sucker for all things pumpkin, apple cider, and all the other cozy, comfort things that come with fall (I can’t wait for football and wings!).
I’ve compiled my family-friendly fall destinations in and around Fairfield County that check off all the fall-themed vibes anyone could ask for!
Tucked away in Norwalk, 314 Beer Garden offers 8,000 sqft of space for drinks, food, fire pits, and games. They offer 14 beers on draft and a full bar plus 314 Wood Fired Pizza, which is super tasty! What I love about this cute spot is how family-friendly (and dog-friendly) it can be. We often see kids playing lawn games while parents sit back and relax.
I also have to applaud them for keeping their event schedule jam-packed. 314 Beer Garden offers live music on the weekends, regular trivia, and pop-up events such as calligraphy and bonsai tree classes. They had a beautiful setup for fall last year with a great pumpkin-filled photo op area and s’mores kits for the fire pit area. Definitely add this to your list on a beautiful day!
This cute spot has so much more to offer than meets the eye! Aside from their very well-known ice cream, Plasko’s offers produce, a nursery, a country store, and a full bakery. They boast about maintaining the rural charm that characterizes Trumbull and draws in crowds year-round. Beginning Saturday, October 2, Plasko’s Corn Maze, featuring an interactive game, will be open to the public every weekend through November 7. Pop in to try their delicious treats and exceptional ice cream (I love their coconut, almond, and chocolate!), grab some pumpkins, and let the kids run off that sugar in the maze. Don’t forget to pick up on some bakery staples like fresh bread and pies to-go!
A fourth-generation family-owned farm is a local treasure offering seasonal activities that are family and dog-friendly! Get lost in their 7-acre corn maze that changes each year to a unique design that is simply breathtaking. They also offer a nightmare, which adds to the spookiness of all things fall with a live band and food trucks. Explore their beautiful sunflower field, enjoy a hayride, check out the farm animals, enjoy treats from their farm stand, and grab your pumpkins! Be sure to check out their event schedule for fun activities such as a Trick or Treating and Fall Festival.
Located in the White Hills part of Shelton, crowds flock to this seasonal destination offering pick-you-own apples with more varieties than I have ever seen! While the entrance is always busy, once you hit the fields, you have wide open spaces for your little ones to run around and taste-test the apples. Once you’ve gathered your harvest (perfect for snacking, apple sauce, pies, and so much more!), head to the bakery to stock up on their famous pies, locally grown honey, cider, and much more!
Head up a bit north to central Connecticut’s rolling hills, and you’ll find Hogan’s Cider Mill, which has been producing cider since 1912. This Instagram-worthy spot offers fun, seasonal treats such as “Blueberry Pancake” (a blueberry brew and maple leaf hard cider drink) and “Potter Potion” (served in a mini caldron, a mocktail blend of creamy caramel and apple with a slight fizz) along with a variety of locally brewed drinks (alcoholic and non-alcoholic). Hosting a massive lawn area with picnic tables, corn hole, mini golf, and more, this family-friendly spot can easily entertain your group for the day. With food trucks and a shop with ice cream, snacks, and salads, you can enjoy this scenic spot on those beautiful fall afternoons!
Head west to Westchester County to check out this family-owned apple orchard that has so much more to offer! While primarily an orchard with seasonal apple picking, Harvest Moon offers a variety of vegetables and stone fruits available at their farm stand along with a CSA program sourced from other local farmers. They produce their own cider and make fresh cider donuts daily, along with other baked goodies that you can enjoy while overlooking their farm. Check regularly for seasonal events, such as Hardscrabble Cider Live Music and pizza nights!
Every year, I attend this ever-changing massive jack-o-lantern exhibit. Located on the grounds of an 18th-century estate on the banks of the Croton River in Westchester, Van Cortlandt Manor hosts this annual event that draws in hundreds of thousands of guests. You will be in awe of the creative designs and massive undertaking to put up this walk–through show.
It takes about 20-40 minutes to walk through but will leave you wanting to go back and do it all over again! With a farm-style pop-up tent filled with Halloween and fall-themed goodies (apparel to snacks and pantry staples) and food and drink stations to keep you warm as you enjoy the display. If you want to make a day of it, visit some of Hudson Valley’s other spooky experiences, such as Spirits of Sleepy Hollow: A Night of Legendary Magic.
Our very own local zoo puts on an amazing Glow Wild Lantern Festival with beautiful, illuminated, larger-than-life lanterns inspired by their wild world. The festival will showcase over 35 large-scale illuminated displays featuring hundreds of beautiful individual and interactive lanterns. Hosted from September 14 through December 2, every Thursday-Sunday (5:30 p.m. – 9:30 p.m. for the glow), this exhibit is also beautiful to enjoy during the day, but certainly visit after dark for the full experience.
Growing up in Monroe, Jones was a staple in our seasonal stops. With 400 acres of pick-your-own fruits and the newest addition of a gift shop, winery, kitchen, and live music, this destination will undoubtedly keep all family members happy! Their Market Yard features farm animals, hayrides, a corn maze, fall flowers, fresh apples, and piles of autumn squash. I always recommend heading early as this is a huge destination spot in the area, so you’ll want to grab your spot at the winery early!
This beautiful spot has so much to offer! The SM&NC has over 80 acres of hiking trails, including The Wheels in the Woods trail which gives people of all abilities the opportunity to enjoy the sights and sounds that our natural setting has to offer (LOVE this inclusivity!) along with the Hecksher Farm with loads of cute animals, playground, an otter pond, maple sugar house and cidery (which produces over 60 gallons of pure Connecticut maple syrup) and a manor which you can explore. Lastly, they just broke ground for a new 11,000 sqft Planetarium II! Check out their calendar for events added regularly, such as a clambake and cider tasting!