Cookstown: Trail, Theater, and Local History

Cookstown brings together a shared-use trail, local history, theater, and shopping destinations. These topics can help you plan your trip: the route through the landscape offers a range of activities, while historic sites bring Cookstown’s development to life. Theater and shopping add culture and a variety of goods to these highlights.

Thornton-Cookstown Trans Canada Trail: Route and Landscape

The 14 km Thornton-Cookstown Trans Canada Trail runs between Thornton and Cookstown, Ontario. As a shared-use trail, it is intended for hiking, cycling, horseback riding, cross-country skiing, and snowmobiling. The options range from walks and bike rides to other activities along the route. It offers a scenic way to walk or cycle and passes through green pastureland and forests.

One notable feature of the route is that it crosses Cookstown Creamery Creek six times. Wildlife may also be a highlight along the way: possible, but not guaranteed, sightings include deer, beavers, rabbits, raccoons, porcupines, foxes, groundhogs, turtles, and various bird species. The combination of shared use, several types of activities, and scenery makes the trail a highlight of its own on your Cookstown trip.

Cookstown’s Local History and Culture

The Cookstown Heritage Conservation District covers around 14 blocks around the intersection of Queen Street and King Street. Its approximate extent and connection to this intersection give the historic district a specific geographic setting. Cookstown was settled in the mid-19th century and was initially called Perry's Corners. By 1847, the place had been renamed “Cooke's Town” after early settler Thomas Cooke; the name later evolved into Cookstown.

St. John's Anglican Church is also among the town’s historic sites: it was originally built in 1852 under the direction of Reverend I. Olsen of Bond Head.

South Simcoe Theatre is a registered non-profit organization in Cookstown that produces a variety of plays and musicals each year. Individual season schedules may change; check the dates for the period of your trip if you have a specific performance in mind. Another historic site is the hall at the location of today’s theater: in 1983, it became the new home of the South Simcoe Theatre group.

Shopping and Getting Around Locally

Tanger Cookstown is at the southeast corner of the intersection of Highway 400 and Highway 89. This upscale outlet shopping destination in Simcoe County offers a selection of well-known brands and local shops. The location of the electric vehicle charging stations is also clearly specified to help you find your way around: they are in the northeast parking lot near entrances 3 and 4.

Nearby, north of Cookstown, is the Cookstown Antique Market. It has two fully finished floors in a 100-year-old barn, with curated antiques, vintage decor, and collectibles from 35 independent dealers. The shopping options are quite distinct: Tanger Cookstown is an outlet destination featuring brands and local shops, while the Antique Market focuses on antiques, decor, and collectibles.

For a broader trip overview: Innisfil.