This Is Connecticut's Quirkiest Little Town
At first glance, Chester, Connecticut, may appear just like any other small New England village. However, its quirky personality quickly becomes apparent. Settled in 1692, the town has had centuries to become a unique and creative hub. It is home to the Chester-Hadlyme Ferry, one of the oldest continuously operating ferries in the country, running since 1769. The town also hosts the Chester Fair, a beloved tradition dating back to 1877. Its peaceful river valley setting has attracted a thriving art community, with galleries scattered throughout town. While the calm atmosphere may be what draws you in, Chester’s eccentric spirit might convince you to stay a little longer.
Art Scene
Chester’s art community is active and well-established, with several art galleries to check out in town. Located on Main Street, travelers will find the Lori Warner Studio/Gallery, which has been a town staple for over 17 years. Here, visitors will find a range of creative and thought-provoking media, including glassblowing, jewelry, paintings, embroidered cashmeres, furniture, and metalworks. Fans of impressionism should also check out the Leif Nilsson Spring Street Studio and Gallery. Nilsson draws inspiration from the natural beauty of the Lower Connecticut River Valley, often painting scenes from in and around Chester. His gallery features landscapes that include views of the Connecticut River, the coastline, local gardens, and the village itself.
In addition to its permanent galleries, Chester hosts a monthly First Friday Stroll that celebrates and promotes the local art community. On the first Friday of every month, from 5 to 8 pm, visitors can stroll down Main Street of Chester Village, appreciating new art exhibitions, live music, seasonal menus, and ice cream flavors. There will also be plenty of opportunities to shop! The next art stroll will be taking place on June 6th of this year.
Music Scene
The music scene in Chester is just as impressive as its art scene. If you enjoy listening to music in an intimate yet elegant setting, you must book one of the Robbie Collomore Concert Series shows. This concert series includes a range of music genres, with upcoming performances including classical music trios, roots & soul bands, and jazz quartets. The location of these concerts in the historic Chester Meeting House makes the events even more special. This meeting house, which dates back to the late 18th century, is one of the few in New England that has been in continual use for over two centuries. It was also extensively refurbished during the 20th century, making the interior just as much of a treat.
If you will be visiting Chester in the summer, you might consider checking out the Concerts in the Garden schedule. Hosted by the Leif Nilsson Spring Street Studio and Gallery, this concert series takes place on Saturday evenings in July and August and features an eclectic mix of jazz and bluegrass tunes. With outdoor bistro-style seating, visitors are encouraged to bring their own picnic and drinks.
Chester Fair
In early 1877, a group of local residents came together to discuss the formation of a society that could promote the town’s agricultural and mechanical industries. Later that fall, the Chester Fair was born as a result. What started as a small gathering back then has turned into one of the county’s largest annual festivals, with people from all over the region coming into town to enjoy the festivities.
There are all kinds of activities to enjoy throughout the weekend, including an antique tractor pull, a livestock competition, a frying pan toss contest, rope making demonstrations, beef jerky making demonstrations, and fiddling demonstrations. There are also plenty of activities for children, like balloon art, a nature center exhibit, stilt walking, and a frog jumping contest. The dates for the Chester Fair this year will be August 22nd through the 24th, so make sure to mark your calendar!
Chakana Sky Alpacas
Anyone curious about meeting an alpaca up close should keep Chakana Sky Alpacas in mind. Inspired by the heritage of Indigenous peoples and animals of the Andes, this Chester alpaca farm has been operating since 2016. This farm is dedicated to responsible care and breeding practices, raising alpacas for sale and producing fiber products that are available in the on-site farm store. Travelers can book a tour of the farm, where Farmer Bill guides guests through the process of raising and caring for alpacas while sharing stories from life on the farm.
Cockaponset State Forest
After spending a day or two exploring Chester’s art, music, and agricultural scene, you will want to make sure to set aside some time to explore the great outdoors! Luckily, the Cockaponset State Forest is right in Chester’s backyard. As the second-largest state forest in Connecticut, this area covers more than 17,000 acres and is distributed across two counties and 11 towns.
Opportunities for outdoor recreational activities are abundant. There are over 100 miles of trails, along with pristine streams, overlooks, and Pattaconk Lake. A few of the potential outdoor activities include hiking, mountain biking, swimming, kayaking, and horseback riding.
If you are looking to explore a different side of Connecticut this year, Chester is a wonderful town to keep in mind. With the summer coming up, music series like the Concerts in the Garden are a great way to learn about local artists. Annual events like the Chester Fair, meanwhile, showcase some of the town’s quirky and most unique and longstanding traditions. Sometimes, the most surprising discoveries are found closer to home than you might expect!
