Essex, CT | A New England Halloween Town

Growing up in Connecticut, I didn’t know about Route 9 until my late 20’s.  Crazy, right?  I passed by it all the time, but I never took the time to venture off of I-95 to go see where it went.  The Chester Bowles Highway is the section of Route 9 that stretches from Old Saybrook to Cromwell, and it encompasses the gems Essex, Deep River, Chester, East Haddam, and Durham.

Our walking tour today brings us to the village of Essex.  Much to my surprise, this trip to Main Street in Essex was my first, and it was long overdue.  I can’t believe I’ve missed out on it all this time!  I went to Essex thinking I was going to take photos of a small New England village during fall, but I quickly found out I would be experiencing so much more.






I arrived at 8:30 a.m. and started my walk down Main Street.  People were so friendly;  how refreshing!  Two people stopped to talk to me, suggesting parts of the town I should photograph, and others said good morning while walking by or running past me.   There were also a lot of people that were walking their dogs and they would stop and talk to other dog walkers.  This close knit, lively community was really making me feel like I had picked the wrong town to live in!  I wanted to be there every week to walk down Main Street and experience their version of small town New England living.







I quickly realized, while walking around, that the residents of Essex really get their creativity flowing and go all out for Halloween!  I was in awe while I stopped to look at each person’s Halloween display.  Many of the displays you see are not your typical Halloween displays – from Frankenstein greeting you, to skeleton dogs, to a creepy butler.  The town also participates in the Scarecrows of the Three Villages competition, so many of the poles in the village are embellished with scarecrows.  The winner of the scarecrow competition gets announced at the Ivoryton Pumpkin Festival at the end of October.  If you are ever in the area during October, I highly suggest you take the time to walk down Main Street to see the displays the residents have taken the time to put together for all to enjoy.
















Much of the town was closed during my visit, but I did make it a point to stop at the Essex Coffee & Tea Company, a charming little coffee shop that had an assortment of baked goods, lattes, and teas.  Their shop’s sitting area brings you back to the way life was before technology with a windowsill adorned with books and an 1980ish stereo standing in the back of the room that’s filled with old records in its encasement.





I also stopped at Gracie’s Corner Toys Ahoy, a gift shop on Main Street, which was just opening as I was starting to head back to my car.  The shop is multiple rooms with souvenirs, collectibles, pet items, toys, games, jewelry, and much much more.  It’s definitely worth a visit if you’re passing through town or you’re a dog lover.  You can see more of what they offer on their Facebook page.





In the market for a new home?  Much to my surprise, there is a lot of real estate on the market in and around the center of town, many of which are beautiful historical colonials.  After my visit, I’m surprised anybody would want to leave this charming New England town.

I did venture off of Main Street for a little while and found a cute little park, that’s open to the public, surrounded by a stone wall with wrought iron fences and inside, a few benches and green crab apple trees.  It seems like a great place to just hang out and read a book during the spring and summer.







I really do need to go back and explore more of Essex because there is so much that I didn’t get to see, but the lighting was getting harsh, and as a photographer, I can’t bring myself to fight with harshly lit photos in Photoshop, so I’m sure you’ll be seeing more of Essex on my blog in the future!












Landmarks Mentioned in Blog Post

Essex Coffee & Tea Company | 51 Main St, Essex, CT 06426

Gracie’s Corner / Toys Ahoy | 43 Main St, Essex, CT 06426

Dickinson Park | Intersection of Prospect Street and North Main Street, Essex, CT

Have you ever been to Essex?  What did you love about it? Feel free to share your experience with me in the comments below!


  1. Gorgeous pictures! I’ve visited Essex a few times in the summer, it’s a beautiful town. Love the New England feel, the lovely shops, the great views of rhe Connecticut River, and of course the historic Griswold Inn. I will have to try to get down there next fall!

  2. just next door is my fav of the tri-town area. Deep River has it’s own charm but tends to get lost by it’s bookends Chester and Essex. You should come the third Saturday of July for the Deep River Muster. You would have a field day photographing the multiple fife and drum corps from around the world and all the Americana that lines the streets.
    BTW your photo’s are GORGEOUS!

    • Thank you Vicki! I will have to note the July date on my calendar, sounds like fun! I came through Deep River because I plan on doing a post on it, but there was a lot of construction that day, so I need to go back!

  3. I’m late to the Essex party here, but my husband and I have been planning our move to small town Connecticut recently. We’re going this October to visit Essex, so I’ve been trying to research all i can online and stumbled on this blog post! WHAT A DREAM! I nearly teared up reading about the people and hospitality you found on the street! I can’t wait to see it in person! I’m also excited to peruse your blog more! We need to jot down an itinerary of places to go while there, I find your blog very helpful.


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