Fall Activities For Kids In Connecticut

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Thank you to Backcountry and ShopStyle for sponsoring this post.

While many of you may not be local – I wanted to round up some of my favorite fall activities for kids in Connecticut and perhaps you can find something similar in your area.   Whether you have kids or not, these are fun ways to get out on the weekends and the outfits are the icing on the cake.   I’m partnering with Backcountry today to share outfits for the family to keep them looking stylish while active.   Backcountry has offered a special discount to Pinteresting Plans readers:  15% off on first purchase  with code “RACHELM15” – woot woot!!

Fall Activities for Kids in Connecticut

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fall activities for kids in connecticut - cute Fall outfit with sorel wedge boots on pinteresting plans fashion blog

Shop Rachel’s Look:  Dylan Flannel and Sherpa Vest XS |  Backcountry White Henley XS  |  Herschel Supply Camo Backpack  |  Alo High Waisted Leggings XS  |  Sorel Joan of Arctic Wedge Shearling Boots  (sized up .5)


Backcountry is my favorite spot to shop for outdoor gear.   They carry an amazing selection of my favorite cold weather boots for the family.  SOREL boots are my fall and winter jam and Backcountry has the best selection!

I started investing in Sorel boots when my older son was born and I was terrified by the fact that I could no longer hibernate inside during snow storms.   Those first Sorel boots I bought 6 years ago are still in amazing shape despite the many Winters they’ve faced.   Backcountry carries so many fashionable pairs of Sorel boots.  I personally find the wedge boots the most flattering because they give the illusion of longer legs.

family in sorel boots - fall activities for kids in connecticut

I can’t get over how adorable the boys’ Sorel boots are but mine take the cake!!    In my shearling lined wedge boots I’m feeling so après ski ready (despite never skiing).  I plan to rewear the Dylan flannel/sherpa vest above with sweater dresses and over sweaters and jeans.

Aside from the cute outfits, I wanted to share a few fall activities in my local area that we make sure to squeeze in each fall.   If you’re passing through Connecticut in the fall – not only check these out – but do say hi while you’re here!

1. Pickin’ Patch (Avon, CT)

I grew up taking hayrides out into the pumpkin patch here.   Because my Dad has been in the hospital we haven’t made it there this year and I heard the pickins may be slim this season?    Fear not!!  They also have a very cute farmstand that sells all sort of funky squashes (and other vegetables) as well as gigantic mum plants.    There is also a food truck on site making apple fritters.  #musthave

2. Heublein Tower Hike (Simsbury, CT)

This quick but beautiful hike is located in my hometown!!  I’ve been making the trek up to the tower for over 30 years.   The initial hike is fairly steep so little ones may need to be carried in a backpack or other carrier, but it’s a quick trip to the top and the view is worth it.   Leaves around where I live don’t usually start to peak until mid October so the hike will be very busy this time of year.   You can bring a picnic, but from the entrance of the hike to the tower will take 30-45 minutes depending how many times you stop to admire the gorgeous view from the top.

3. Fair Weather Acres Fall Festival and Corn Maze (Cromwell, CT)

We haven’t been yet this year but I’ve shared a lot of Fall photos from this pumpkin heaven in years prior.   There are tons of kids activities – not limited to a corn maze and a semi enclosed playground filled with corn kernels.   I avoid filling my pockets and underpants with corn kernels but my kids are all in on that attraction.   My husband loves to go for the cider donuts.

4. Belltown Orchard (Glastonbury, CT)

This pick your own apple orchard (pears also available for picking) gets very packed on the weekends.   They have a snack bar that serves cider donuts and tractor rides around the farm.  Last year I got scolded for taking a photo there – hence why you don’t see me picking apples in any of these photos :).

5.  Westmoor Park (West Hartford, CT)

Nestled in our current hometown Westmoor Park is great for smaller kids who aren’t interested in a longer foliage hike.  The park has live animals you can get up close and personal with as well as short, flat walking trails small children will tolerate much better.    They used to offer a free fall family fair but it looks like now you register for similar events.    The park relies on donations so they have a lot of fundraisers – like a “feast on the farm” dinner.

We visit Westmoor Park year round because it’s just a few minutes from our house.

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(and don’t forget you can get 15% off discount code on first purchase “RACHELM15”)

Rachel’s Outfit:  

Shop my Sorel wedge boots (sized up 5.) here, brimmed knit beanie, and Alo leggings (wearing XS) here and the tops below:

Chris’ Outfit:  Shop the camo backpack here, the rest of his outfit below:

My Kids’ Outfits:


Thanks for stopping by!   There are so many things to do in Connecticut in the Fall.   If you’re local I’d love to hear your favorite activities.  Please drop a comment below!




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