5 Connecticut/ Travel

8 Fun Fall Things to Do in Connecticut

Apple Picking Lyman Orchards

Hard to believe it’s officially September — and almost a week into it, too!  While I’m off at NYFW having an absolute (crazy) blast, I’m secretly so excited to get back to CT and start enjoying all of my favorite fall activities.  We were traveling in Europe through most of September and October last year, so I’m pumped to be here during my favorite season this time around!

I’m sharing my 8 favorite things to do in Connecticut during the fall season — everything from pumpkin and apple picking, to some of my favorite events throughout the next few months that you should get on your radar!

Apple Picking at Lyman Orchards.  I’m an apple lover (favorite fruit EVER), so I’m in my element during the fall season, especially here in CT.  I could seriously eat an apple every single day (always with almond butter), so I stock up on a bundle of apples and love picking them and taking in the gorgeous views!  Lyman Orchards in central in CT and easy to get to from just about anywhere.

Grabbing an apple cider donut and fresh apple cider from Beardsley Farms.  I’m partial to this because I grew up within walking distance from here  (in Shelton, CT) and I’ve become somewhat of an apple cider donut snob due to their sheer amazingness.  It’s hard for me to even compare other apple cider donuts to these.  They are BEYOND.  They also make their apple cider and serve in hot in a “serve yourself” area within the shop.  It’ll be hard for you not to walk out with a dozen pastries and everything from sauce to salsa to jam made with the Beardsley apples.

Greenwich Food & Wine Festival.  Hands down, one of the best CT Food & Wine fests there is.  Tim McGraw is headlining it this year — and there’s always so many celebrity chefs making appearances.  What I love about this festival is there is actual FOOD.  Not even bites.  FOOD.  We’ve gone to plenty where it’s a free for all with booze and they skimp on the food.  You can grab some of the best food from around the state while watching chefs cook and compete with one another, and then finish the night with a country concert.  We’ll be away at the Newport Food and Wine festival this year for a project during the same weekend — otherwise, we would be here!

Pumpkin Picking at Jones Family Farms.  Another farm right around the corner from my parent’s house in Shelton, CT (and the house I grew up in), I make it a point to go here every single year with my mom and it’s always so much fun.  We are obsessed with the tiny white pumpkins and the Cinderella pumpkins and always come home with waaaay too many!  This is such a family friendly place too, so if you have little ones — take them on a hay ride and let them meet the farm animals!

Wine Tasting at Gouvea Vineyards.  You’re not here for the wine as much as you are for the view.  Pack a picnic and head over to this absolutely breathtaking vineyard to see the most stunning rolling hills with all the foliage.

Hiking to Heublein Tower.  After guzzling too much wine and eating waaaay too many ACDs — we’re usually itching for a little excercise.  We love hiking to the top of Talcott Mountain in Simsbury to take in the most gorgeous views in our area.  Once you reach the top, you can actually take a tour inside the tower (which used to be a residence).  I won’t spoil it, but there’s a really fun backstory for why there’s a tower that big in the middle of the woods!

Warming up with a coffee at Dom’s Coffee.  My favorite local coffee spot that has the absolute CUTEST fall decor ever.  You’ll see why I can spend all day here — especially in the cooler months!

Get scared AF at a haunted house.  Actually more like a haunted trail… we’ve gone to the Trail of Terror in Wallingford and it’s INSANITY.  So much fun and good for a group if you’re looking for something to do one night!

Pumpkin Picking Jones Family Farms
Connecticut Foliage

Apple Cider Donuts Connecticut

Pumpkin Picking Connecticut

What are your favorite things to do in Connecticut and New England?!  Let me know in a comment!


  • Reply
    September 5, 2018 at 10:10 pm

    Great post. Can’t wait for the fall!



  • Reply
    September 6, 2018 at 1:12 am

    Wine tasting and pumpkin picking are something I always do each Fall! 🙂


  • Reply
    September 9, 2018 at 11:23 am

    Love that you have two Simsbury/Avon things on this list! Both the Tower and Dom’s are around the corner from where I live! The tower is such an easy pretty hike and Doms coffee is the best! The decor there is amazing AND Dom’s also has an amazing cheese shop right inside. Thanks so much for this list and for your blog! Love it!

  • Reply
    September 17, 2018 at 11:36 am

    Do you buy the tickets to Greenwich wine and food festival? If yes then where? And what day would you recommend to go on? Thanks

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