Chester, CT might just be the most charming small town in New England. It is quaint, unique, artistic, and damn cute. (Yes, I said cute!) The main street is filled with small boutiques, galleries, and truly excellent dining. There is engaging architecture, hiking trails, marinas, waterfalls, and state forests. Chester, CT is filled with great things to do and see. It is the perfect day trip destination and would be great for a date night. (I should know I live close to Chester!) So keep scrolling for the 8 best things to do in Chester, CT.
At Pragmatic Travelers, we only recommend what we have actually done and eaten. We never recommend something we haven’t experienced. .
Explore Chester’s Main Street (Downtown)
Downtown Chester is a must-go when visiting the small town. This is where you find most of the restaurants, galleries, and boutiques. Make sure to check out Lark. It is filled with goodies to browse through. It is in a beautiful brick building. I also like browsing Blackkat which is a leather goods store. You can watch them at work while you visit. Take your time and enjoy this main street. Maybe with an ice cream in your hand.
Eat The Food in Chester
Speaking of ice cream. You must dine at one of the restaurants in Chester. For such a small town, they are filled with very high-quality restaurants. Like the small batch ice cream shop called Honeycone.
Check out our best restaurant guide to Chester for more details.
Grab a pint at Little House Brewing Company
Wash down your meal or ice cream with a cold pint from Little House Brewing Company. This is a microbrewery with indoor and outdoor seating. It is located in the heart of Chester’s historic downtown. Adorable brewery with great beer. A wonderful addition to your time exploring Chester.
Attend a First Friday
On the First Friday of every month the historic downtown of Chester comes alive. Stores stay open later and offer special sales, restaurants offer special appetizers or drinks and so much more. It changes each month and could be a great beginning to a date night.
Catch a show at Goodspeed Opera House
Goodspeed has its Opera House in East Haddam (very close to Chester) and uses the Norma Terris Theater in Chester as well. SO this counts as something to do in Chester. The Goodspeed hosts new and newly revived musicals all year. The Opera House is a historic building right on the river. It is gorgeous. Combine a show with dinner in Chester and boom perfect date night!
Visit Chester Village’s Starry Night
This is one of my absolute favorite things about Chester. During the holiday season, the entire village twinkles with over 150 glowing stars. This is an art installation by local artist Christopher Owens. This makes shopping and dining so magical. The entire family will love wandering around Chester as it glows. Please watch the video below from drone operator Frank DiNardi as it does a much better job of demonstrating how beautiful this is.
Visit Cockaponset State Forest
Cockaponset is the second-largest state park in Connecticut. This beautiful state park is filled with different activities like fishing, hiking, swimming, mountain biking, and so on. The Pattaconk Reservoir Trail is a great easy walk around the lake. A great day trip could include a hike through the forest followed by ice cream at Honeycone.
Visit Gillette Castle
Ok, so this is technically not in Chester but it is only a 20-minute drive away and even less if you take the ferry. The Chester Hadlyme Ferry is located in Chester so I stand by my decision to include this. This castle was built by actor William Hooker Gillette in the early 1900s. It was built to look medieval on the outside but the inside is much more modern. It is a funky place to visit with sweeping views and loads of walking trails. Highly recommend.
Your Thoughts…
These are the best things to do in Chester, CT. What are your favorite things to do in Chester, CT? Leave a comment.
