Fall Is In The Air…

Fall is my favorite season! The crisp air, the sunny days, the smell of a crock pot working all day, the festivities…I seriously think there is no better season!!  There are so many fun, seasonal activities to do in Connecticut with my son Jaxson and I’m sharing my favorites with you as well as some new ones that made it to our list our “Fall Bucket List”. No matter your city or neighborhood, you’re sure to find some festive activities around your area this Fall!

Chowda Fest in Westport

For $20 on October 1, enjoy unlimited sampling from over 40 vendors and rate the chowdas that are your favorite. It’s kid and dog friendly too! This event runs from 11am to 3pm so get there early!  Bring your appetite, try some culinary creativity, enjoy some chowda, brew, and water views. I love a good chowda and this is the event to NOT MISS!

Fairfield Food Truck Festival at Jennings Beach

Who doesn’t love sampling food from local food trucks?! From noon to 7pm this Sunday and for only $5 (children under 12 eat free), you’ll get to sample from a variety of food trucks. The wristband you’ll get will last you all day, so you can come for lunch, leave, and come back for dinner. $5 for two meals?! Count us in! Some of our favorite food trucks will be there, including Super Duper Weenie, Fire Engine Pizza, The Local Meatball, Happy Ray’s Ice Cream and more!  We will be there, and I am sure the kids will build up an appetite at the playground first!

Apple and Pumpkin Picking

Apple and pumpkin picking – a staple of Fall activities! Bundle up your kids in their boots and scarves and head over to an orchard. Luckily for us, Connecticut has a TON of orchards packed full of apples and pumpkins ripe for the picking. We love Lyman Orchards, Jones Family Farm, Silverman’s Farm, Blue Jay Orchards and Beardsley Cider Mill.  Truth be told, this Fall hasn’t felt like Fall, rather we have been experiencing summer temperatures SO….apple picking is still on our to-do-list but this weekend you can find us at Jones Family Farm, picking up pumpkins, going for hayrides, and enjoying the day with our friends!

Railroad Museum of New England’s Fall Foliage & Pumpkin Patch

Ahh… is there anything better in the fall than riding a train over the river and through the woods through beautiful Naugatuck Valley and seeing the beautiful foliage? We sure don’t think so. This train ride stops at a pumpkin patch and kids can choose their own pumpkin to take back with them. It’s a fun activity (and has been on our list to do) that’s sure to keep kids (and adults!) of all ages entertained…what kid doesn’t love a train ride?!

Greenfield Hill’s Pumpkin Festival

From 10am to 3pm on October 7th in picturesque Greenfield Hill, you’ll get to experience Fall in all it’s glory. From hayrides and scarecrow making to pumpkin decorating and Audubon exhibits, this has it all! I think it’ll be a great place to gather with friends, have the kids run around, and take some pretty photos against the cornfields and pumpkin patches. I love to support the local farms…I think this event is a town favorite and tends to have a great turnout!  The setting is just perfect, the kids run into friends from school, there are tons of crafty activities, fresh apple cider and baked goods!

The Great Jack O’Lantern Blaze in Croton-on-Hudson, NY

To get in the spirit of Halloween, start off with a visit to Hudson Valley’s Great Jack O’Lantern Blaze. Open most of October and select weekend days in November, this is a fun trip for people of all ages! This will be our first year experiencing the Blaze and I think it will be a hit!

Fall Hikes With Kids

This is a fun one and oh so convenient. We hit up our favorite brunch at the Gray Goose (I can never say no to their lobster eggs benedict) and head over to Southport Park. It has a cute tree house, slide, a river, and it’s an easy and quick walk. Jaxson looks forward to exploring in the woods and looking for cheetahs (hey, a kid can dream). We also love Brett Woods, the CT Audubon Society and Lake Mohegan. We are so lucky that Fairfield has so many parks and trails, and with the leaves changing colors soon, our hikes are sure to be magical!  After the hike, the kids can get creative and decorate a “Haunted Cookie House”…stop into any Trader Joes and buy a kit!

Stew Leonard’s Fall Events

What’s Fall without a hay ride? Our favorite grocery store, Stew Leonard’s, is hosting a ton of events all throughout the season, including their famous hay rides.

Halloween on the Green in Fairfield

Reason 1,385,826,927 I love living in Fairfield!  On October 29, put on your Halloween costumes and get down to the Fairfield Museum & History Center for a ton of activities and fun! Formerly called “Trick or Treat on Safety Street,” this town-wide event includes a costume party, crafts, games, displays and so much more. We can’t pick a favorite event, there are too many to choose!

I could go on and on about things to do in and around Fairfield County in the Fall…I could also repeatedly tell you how much I love the Fall and why but instead, make note of some of these kid-friendly events on your calendar and go enjoy!! You won’t be sorry!


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Shoshana Snyder

Shoshana Snyder


Sarah Pritchard

Sarah Pritchard


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