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What to Expect at the Chester Fair

Chester, Connecticut, is a small town with less than 4,000 residents that enjoys a scenic location on the Connecticut River.

Chester is perhaps best known as the Pattaconk Recreation Area's home, although the abundance of marinas just outside the downtown area is also notable.

Chester doesn't attract the same crowds in the summer as nearby Old Saybrook and Westbrook because it isn't a beach community. However, for a few days every August, Chester becomes the place to be in Coastal Connecticut because of the Chester Fair, an annual event that got its start in 1877.

Here's some information on attending the Chester Fair and what you can expect once you get there.

The Fair's History

Known locally as simply The Fair, this event started in 1877 when some local men wanted to create a society to support the town economy's main drivers: farming and mechanics.

The idea was to organize an exhibition to help fund these industries, and the men held the first event later that year. Although it was a small gathering, it paved the way for The Fair to grow in the coming years. 

The event was finally able to charge admission in 1880, and its expansion took off from there, attracting new exhibits every year.

Today, the Chester Fair has its own grounds just off Water Street and draws residents from all over the Connecticut Shoreline when it takes place every August.

The Midway

One of the main annual attractions at the Chester Fair is the Midway, which features all of the rides you'd expect at a fairground. Whether you're into riding on the Ferris Wheel or putting the kids on the Carousel, the Chester Fair has something everyone is sure to enjoy.

There are carnival games and concessions throughout the Midway, too, and it's open all three days that the fair runs, including from early in the morning until late at night on the Saturday.

Live Entertainment

Even if you aren't into the Midway rides, you can enjoy the live entertainment at the Chester Fair. There are options for the entire family, including live music, dog agility displays, tractor pulls, livestock judging, and sheep herding demonstrations.

Some of the most popular events at The Fair are the pig races, which take place around an oval track and always attract a crowd.

There are children's activities, including balloon art, animal encounters, acrobats, and pedal tractor races, too.

The entertainment is nearly endless at the Chester Fair, giving locals more than enough reason to visit annually.

Concessions and Vendors

We mentioned that there are concessions at the Midway, and you'll find other food vendors all over the grounds. There's a beer tent, too, so you can grab a cold one while the kids go on some rides or after taking in an exciting pig race. 

You can also buy crafts, and other handmade items, much like you'd find at a flea market. This inclusion allows local vendors to sell their products to community members, which is in the spirit of why organizers started The Fair in the first place.

Getting There and Admission

The Chester Fair takes place every year toward the end of August. It runs for three days - Friday, Saturday, Sunday - with the gates being open from 8:00 AM until 11:00 PM on the Saturday.

Admission to The Fair is $8 for adults, and $6 for seniors, while children 12 and under are free. Adults can also grab a pass for all three days for $21. 

There's a large parking lot at the venue that is free to use for the entire weekend. Officials do a pretty good job organizing the parking area, helping it remain accessible despite the large crowds.

As for the Midway, you can purchase a wristband on the Saturday and Sunday for unlimited rides or pay for individual rides throughout the day.

Getting to the Chester Fair is simple, as the venue is on Kirtland Terrace, which enjoys a convenient position where Water Street and Middlesex Avenue meet. 

A Must-Do For Chester, CT Residents

The Chester Fair is known as a gathering spot for residents every year. This event provides a chance to connect with people you haven't seen in a while or meet new friends after relocating to this small community near the Connecticut Shoreline.

You might not understand what The Fair means to the people who live here until you experience it yourself, but once you buy a home in Chester, CT, you'll quickly fit in after your first visit to this event.


Published February 26, 2021 in Exploring Our Area