Spring Fling
This annual event is held the first Saturday in April with local merchants, artists, and crafters gathering in the Courthouse Square. A variety of food and drink is available from local organizations and the kids always look forward to visiting with the Easter Bunny.

Farmers Market
Local growers sell their produce and wares each Saturday morning on the north side of the Courthouse Square. The market opens in late spring, depending on the weather, and remains open until the end of October.

Porta Westfalica
This annual event is held the third Tuesday in June in honor of the Sister Cities partnership between Waterloo and Porta Westfalica, Germany. The festival is held on the Courthouse Square with plenty of food and drink. The traditional German fare of pork sausage and potato pancakes is available. The Waterloo German Band and the Waterloo Municipal Band perform throughout the evening. There is a parade featuring floats and marching bands.

Monroe County Fair
The Monroe County Fair usually begins the last Sunday in July and runs through the following Sunday. The annual event is held at the Waterloo Fairgrounds, located on the west side of the City along Route 156. Fair exhibits include farm implements, farm animals, arts and crafts, 4-H projects, floral arrangements, art and photography, quilts, and garden produce. Carnival rides are also featured. Local organizations offer food and refreshments. The Fair grandstand events range from tractor pulls to the FFA competition and the annual Fair Queen Pageant and the Little Miss contest. One of the more popular events is the demolition derby. The Fair also has many events related to horses.

Waterloo Homecoming
The Waterloo Homecoming is held annually the last Friday and Saturday in August on the Courthouse Square. The event features live music, carnival rides, games, and plenty of food and drink offered by local organizations. A parade is featured on Saturday with floats, marching bands, and other items of interest.

Heritage Fall Festival
Local merchants, artists, and crafters gather on the Courthouse Square to sell their wares. A local chicken wing competition allows patrons to sample and vote for the “Best Wings in Waterloo”. Other food and drinks are also available. A petting zoo and carriage rides are featured. This event is held the second Saturday in October.

Halloween Check Point
The Monroe County EMS and the Waterloo Police Department host this event at the Waterloo Police Department, located at City Hall, on Halloween from 6:00 p.m. to 9:00 p.m.. Food and drinks are donated by local businesses and provided free of charge to children.

Christmas Walk
The annual Christmas Walk sponsored by the Waterloo Merchants is held the Sunday after Thanksgiving. Local merchants are open for holiday shopping. Also featured are carriage rides, Santa’s cottage and a Christmas concert.