Chester, CT is an incredibly attractive and charming small town with a plethora of great dining options. I mean seriously, some of my favorite restaurants in Connecticut are in Chester. Also, some of the best restaurants in the state are in Chester. So don’t sleep on this small town and its yummy food. Did I mention the food was great?! Keep scrolling to find the 6 best restaurants in Chester, CT.
At Pragmatic Travelers, we only recommend what we have actually experienced and eaten. We wouldn’t recommend a restaurant we haven’t eaten at.
Make a full day of it in Chester with our favorite things to do in Chester, CT.
Grano Arso- $$$
Let’s start with the heavyweight. Grano Arso is one of the best restaurants in CT, let alone Chester. It has won numerous awards for its stunning food. You will think of their homemade pasta long after the meal is finished. Ingredients are mostly local and based on the season. Their cocktails are truly something special like the Grano Old Fashioned. The interior is both cozy and trendy. I honestly can’t say enough good things about this restaurant. However, it is very expensive so I would categorize it as a special occasion restaurant. Reservations are always a good idea.
River Tavern-$$$
River Tavern doesn’t get enough recognition. This is a great restaurant in Chester that specializes in local flavors and products. It is very small inside with some great outdoor seating overlooking the main street of Chester. Reservations are always a good idea. The food is interesting, fresh and very delicious. The date pudding is what dreams are made of. Another great option for cocktails in the area. Cocktails and golden hour with their outdoor seating…chef’s kiss!
Honeycone Craft Ice Cream-$
I didn’t know I needed small-batch artisan ice cream in my life until I went to Honeycone Craft Ice Cream. Sweet mother of all things good. This place is amazing. Nearly everything is made in-house: the cones, ice cream, sprinkles, marshmallows, European hot chocolate, etc. And you can tell. The quality of this ice cream stands out. They have yearlong flavors but the seasonal ones are something else and keep you coming back for more. I am obsessed with their pecan pie ice cream with chunks of actual pecan pie running through it. I would trade part of my soul to have that available outside of November.
Otto Pizza-$/$$
Otto’s pizza is fantastic and is up there among my favorite pizza places in Connecticut. This is a great pizza joint with a very thin crust, fresh toppings, and innovative pies. Not to mention a great local beer list and an amazing outdoor seating area. This seating area is under a massive tent right on a small river. Gorgeous. Don’t skip this!
Rustica Ristorante-$$/$$$
Rustica Ristorante is an excellent spot for homemade/fresh pasta. The pasta is very good but then nothing can beat freshly made pasta. It is not as glamorous as Grano Arso and the cocktails are not as good. However, it is a solid spot for pasta and a bit more affordable. It is also outside of the main bit of town so the location isn’t as exciting. However, it is still a very good restaurant. You won’t be disappointed.
Thai Riverside-$/$$
I was pleasantly surprised with Thai Riverside. The food is incredibly good and affordable. I loved the papaya salad and Thai street noodles. The menu is large and has something for everyone. It is a small but cute restaurant with excellent service. It is a great affordable option while exploring Chester. I highly recommend it.
Your Thoughts…
Here are the 6 best restaurants in Chester, CT. Have you tried them? Where else do you like to eat in/near Chester, CT? Leave a comment below.
