The Chester squirrel designed by graphic artist Peter Good, a longtime Chester resident, has become an iconic emblem of the town, particularly on T-shirts at the Fourth of July road race. But now Rebecca Joslow MacGregor, involved in the community-wide Reopen Chester initiative, and the Chester Historical Society have created additional squirrel tributes: two walking tours of the town named, in honor of Chester’s favorite rodent, Chasing Squirrels.

The tours, with information provided by the historical society, highlight the town’s history through descriptions of landmarks along the walking route. Maps are available at the historical society’s website, and using the numbers marked on the map, walkers can stop at each site and read the accompanying story. Joslow MacGregor has also stenciled squirrels in front of the landmarks involved.

Chasing Squirrels is a wealth of local lore: how what was once the C.J. Bates factory became the Goodspeed at Chester, what unusual trick basketball players used to confuse opponents when Chester had its own high school and the team played in a large room on the second floor of 4 Water Street, and where, at the turn of the century, Chester’s Junior Prohibition Club met.

Joslow MacGregor got the idea for the walks by walking herself. Now a New York City resident, COVID-19 and its resultant changes mean longer visits to Chester to see her parents Doreen and Jon Joslow. Although she had grown up in Chester, Joslow MacGregor found as she walked her Jack Russell terrier that she was seeing her community with new eyes.

She thought that looking at Chester through the lens of its past would make fascinating walking tours, an activity that could encompass the required social distancing while providing outdoor exercise.

“It’s an activity people could do on their own at different times,” she said.

The maps and historical information are all on the Chester Historical Society website chesterhistoricalsociety.org. Joslow MacGregor pointed out people could even access the information on their cell phones as they walked.

There are two short routes, Up North, starting at the Stone House on North Main Street and going up to the Chester Meeting House at Liberty Street with detailed information about eight sites along the walk, and Out West, again eight sites, also starting at the Stone House and continuing up West Main Street to the building that once housed Chester Union School, now the location of the Chester Hose Company, and finishing at what was once a popular meeting place in town, Bradley’s Hall, now renovated as two apartments.

Cary Hull, president of the Chester Historical Society, said she didn’t know how many people had done the walking tours but she knew people had gone online to read the historical descriptions.

Deck the Halls

In addition to the walking tours, Joslow has spearheaded a holiday house decorating contest in conjunction with Chester Presto ACT, the arts, culture, and tourism committee of the Chester Merchants Association.

Participating homes had to register by the end of November and decorations must be up by Monday, Dec. 14. From the evening of the 14th until Thursday, Dec. 17, people are encouraged to take an automobile tour of the homes and vote for their favorites in three different categories: brightest, best decoration, and funniest.

The town website chesterct.org will have a map of the homes involved and the town is also planning to send out an e-blast with the information in time for people to view and vote on the decorations online. Chester Presto ACT is also planning to have a map of the homes on its website and information about voting.

The emphasis, whatever the holiday celebration, is to decorate with the bright lights that illuminate the darkest days of the year.

“The decorating brings light and joy to the season,” said Mandy Carroll, head of the merchants association.

Find route maps for the Chester Squirrel walks atchesterhistoricalsociety.org.

Information on viewing Holiday Homes will be forthcoming at www.instagram.com/chesterprestoact and the town website www.chesterct.org.