Chester, Connecticut is a small rural town sandwiched between Essex and East Haddam. I discovered this town a few years ago in May during their town wide tag sale. They hold one annually around Memorial Day weekend. It’s so good that I’ve gone there three years now. I wondered what Chester looked like on an ordinary day so I took a drive up one Sunday.
When I arrived, I had came right at the end of their Sunday Farmers Market (drats!). They shut down the main street every Sunday from 10am-1pm for the farmers market from June-October. I saw a few vendors and was impressed enough that I wish I had came a little earlier!
The main street sits in the village center where there are many unique shops, restaurants, coffee shops and galleries. I felt like I was in a time warp! The village had many historical buildings. There was an Italian restaurant in a bank building. The majority of historical houses had shops. Chester was carefully landscaped to enhance the beauty of its historical charm.
I started out with a lunch at Simon’s Marketplace. I was overwhelmed by the dining selection on main street but it was the general store vibe that drew me in. Simon’s Marketplace is a gourmet general store offering sandwiches, soups, salads and desserts. There was a coffee bar too. The place felt like a combination of a deli and cafe creating a very cozy environment. There was a small gift shop of unique gifts. I had my dog with me for the day so I couldn’t dine inside, but they had tables out front of the store. The store was perfect centered on the main street so it was a great spot for people-watching! I ate the Mayflower wrap - a taste of Thanksgiving with turkey, cranberry and stuffing. Yum!
My furkid was itching to explore so I took her to the pet supplies store - Strut Your Mutt. It was a cute small shop with all goodies for pets. There were local made treats to purchase too! The staff was very friendly and talked to everyone that came in the shop. She told me more about the farmers market that I had just missed. She was helpful with giving me a brochure listing all shops and events in Chester. I wasn’t sure how dog friendly Chester was, she informed me that pretty much all stores allowed dogs including the brewery that was across the street!
I checked out a few shops on the main street. First store I stopped in was The Perfect Pear, a kitchenware store. Their dutch door was adorable! I have never see many stores with that kind door! I definitely walked into a foodie’s dream store. It was well stocked with kitchen goodies and decor for your home.
Blackkat Leather probably had my favorite smell of any shops I walked into. Leather. It smelled so new! The shop was full of handmade leather goods such as purses, wallets, belts, bracelets, etc. I admit that I’m not typically into leather goods but I could tell that the craftsmanship of the products was impressive.
My favorite gift shop was The French Hen - Gift Boutique. I had visited this shop when I came through Chester before during the town wide tag sale. There are unique gifts for every occasion. The shop was carefully organized by theme of the products. My favorite section was the nautical table, of course! This shop is always a stop every time I come to Chester.
I was very intrigued when I walked into Cait Shea - a women’s clothing store. The owner, Cait actually designs and handmade all of her clothing right there in Chester. I love that her clothing isn’t mass produced so if you purchase something from her shop, you have a one of kind piece! Her shop was combined with Sprouted - a coffee & tea bar. They serve organic coffee and local made teas. (NOTE: Cait is moving her shop to Ivoryton, CT which borders Essex. You will have to put this on your Essex must see list!)
The last shop I visited was The E List - another women’s clothing store. I was particularly excited when I recognized the logo from the website. I learned about the website after seeing Erica hosting a book tour with Nicholas Sparks when he visited New London, CT. Her website had guides of where to see, eat, do on CT shoreline. I had no idea that she expanded into a storefront in Chester. The store had apparently opened this past spring. The shop was housed in a beautiful historical building. There was a good selection of women’s designers clothing. The clothing is beautiful!
To end the lovely Sunday afternoon in Chester, I went to Little House Brewing Company. You can’t miss the gray house with the brewery logo. The house itself was a historical, built in 1836. There were outdoor patio seating which was full - no surprise because it was a beautiful summer day! There were more outdoor garden patio out back. I walked inside to a tavern setting with high tables, couches and bar counter seating. I decided to sit on the comfy couch near the front window that overlooked the village of Chester. They offered a variety of beer but I got the cherry cider. I’m obsessed with anything cherry flavored. Lemme tell you, this cherry cider was AMAZING. I wish they sold it in bottles for me to take home! Right now, their products are only sold in house and at some bars across CT. The brewery was started from a Kick Starter project! I really enjoyed the relaxing atmosphere. The folks were so friendly and you could feel the sense of community. The best part is that it was super dog friendly. They even have an adorable brewpug running around named Kirby.
At a first glance, you will be surprised at how small Chester main street is - only half mile long. I promise that it is worthwhile to visit the village. I really enjoyed the slow paced afternoon socializing with all the friendly townspeople and appreciating the historical charm. The town wide tag sale in May is always amazing so be sure to check that out too! It’s fun meeting people and seeing the beautiful homes all over the town of Chester. The community is so friendly that you feel like you’re a local.