
My family and I love day trips, especially in the summer. New England has no shortage of wonderful places to visit! Recently, we found a Connecticut town so full of charm, we can’t get enough of it! Grab a lemonade and come take a visit with me to Chester, Connecticut!
We have lived in Connecticut, in Sandy Hook, for over thirty years. My husband has traveled all over the state for his job, and we have gone on road trips here and there across the New England area since we moved here over three decades ago. We thought we had seen most everything in the state. When my daughter found a town we had not heard of before, we were intrigued!
An hour and ten minutes from where we live, Chester, Connecticut is a small coastal town, nestled along the Connecticut River, with a population under 4000 in the last census. The town is bursting with charm! The homes, the buildings such as the library, and the surrounding area are so quaint and charming, and it is a friendly town. Rich in history, the Main Street looks like it could be part of a movie or storybook, reminiscent of a small hamlet you might find in Europe, perhaps.



We were first recently drawn to Chester when my daughter saw an Instagram ad for a small local store there. We LOVE to read, and love many of the same books and genres, one being romance. There is THE most wonderful romance-only bookstore in Chester.


This bookstore, Montgomery and Taggert, is so charming, it looks like the store itself looks as if it is out of a novel! Walking through the parking lot to the entrance, you cross under a beautiful archway covered in vines, to the beautiful English-style garden full of flowers and herbs, where you almost expect to see Mr. Darcy!



Inside the store, there are all sorts of beautiful books and gifts. There are all types of romance-themed books, from Jane Austen and other classics, to modern-day “cozy” and “cottage core” romance novels, with plenty of beautiful “painted edge” books that I love so much!

Walk from the bookstore to the corner, and there is the bustling, quaint Main Street. Planters brimming with flowers, cobblestone in the sidewalks, amazing restaurants and stores with artisan wares make Chester a perfect destination.








Ask the shopkeepers in town for a good restaurant, and the answer is the same: all the restaurants in Chester are noteworthy and delicious! The first time we went to Chester, it was just my daughter and myself in early June. We walked around, and ate lunch outside on the patio of the Pattaconk 1850 pub. It was so delicious, we ate there again when we returned to Chester last week with my friend, Alison, and her daughter for a fun “girls day out”!
After our lunch, the four of us ended up walking all the way to the end of Main Street, to a local beautiful cemetery, open to the public. It was hauntingly beautiful and peaceful.




On both visits, we ended the day on my favorite note – ice cream! The BEST ice cream I have EVER had is found in Chester, at Honeycone Craft Ice Cream. Owned by a mother-daughter team, the ice cream is truly Heavenly. The vegan ice cream is to die for (Vegan Coconut Cream was delightful), but right now I am just over the moon for their dreamy Blackberry Basil ice cream (we bought pints to bring home it is so scrumptious)!


On Father’s Day, we even drove to Chester just for an ice cream at Honeycone, and brought home a delicious wood-fired pizza home for dinner from OTTO pizza.

After living over thirty years in Connecticut, Chester is on my list of favorite places to visit, and certainly worth checking out if you are in New England! There are art galleries, shops, and special events that occur downtown – “Chester’s First Fridays”, special Friday evenings where stores and galleries stay open late, with live music and other specials. A visit to Chester is refreshing! I am so glad we found such a tranquil, beautiful little village. Tell me, do YOU have a favorite town or area that you love to visit for the day? Share with me in the comments!

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