The area around Port Perry was first surveyed as part of Reach Township by Major Samuel Street Wilmot in 1809. The first settler in the area was Reuben Crandell, a United Empire Loyalist who built a homestead with his wife in May 1821. Their original home is still in use and can be seen on King Street between Prince Albert and Manchester. In November 1821, Lucy Ann Crandell became the first child of European descent born in the area. In 1831, Crandell and his family moved to a homestead at what became Crandell's Corners (later called Borelia).[3] It had its own Post Office, near the present-day junction of Queen Street and Highway 7A.
Settler Peter Perry laid out village lots on the shore of Lake Scugog in 1848 on the site of a former native village known as Scugog Village. The townsite was named Port Perry in 1852 and its first Postmaster was Joseph Bigelow. It was incorporated as a village in 1871. At the time there was an intense rivalry between Port Perry and two nearby towns, Prince Albert and Manchester. Expecting great things for "his" town, Peter Perry predicted that goats would eat grass off of Prince Albert's main street.[4]
At the time, Prince Albert sat astride a planked toll road running south to Whitby. Grain and lumber from areas throughout the area south-east of Lake Simcoe fed through Prince Albert, which was a major grain trading area. Perry and others in Port Perry felt a railway was a much better option, and Perry's prediction would eventually come true.
A group of local businessmen started the process of bringing the railway to the town in 1867, and the first train on the Port Whitby and Port Perry Railway reached the terminus in Port Perry in 1872. In the following year the grain elevator was built, still standing today as Canada's oldest existing grain elevator.[5] Cargo from all over northern Ontario was shipped via the Trent-Severn Waterway to Port Perry via Lake Scugog, and then via the railway to Whitby, where it could be loaded onto the CP or CN mainlines running along the shore of Lake Ontario, or onto ships in Port Whitby. Businesses quickly moved out of Prince Albert and moved to Port Perry, leaving Prince Albert effectively a suburb of Port Perry today. The Port Perry Granary still stands as a tall sentinel on the shores of Lake Scugog and proud of being Canada's oldest grain elevator outlasting numerous fires and modern day demolition.
The village was amalgamated with Cartwright, Reach and Scugog Townships to form the Township of Scugog in 1974 upon the creation of the Regional Municipality of Durham.
An Ontario Historical Plaque was erected at the Scugog Shores Museum by the province to commemorate cartoonist Jimmy Frise's role in Ontario's heritage.[6]
Port Perry's Victorian-era downtown is a tourist destination, with clothing stores, restaurants, cafés, bookstores, galleries and antique shops. In the summer, the town features the festivals Mississauga First Nation Pow Wow, the Highland Games, the Dragon Boat Races and StreetFest. Port Perry is also home to the Theatre on The Ridge summer theatre festival featuring 6 shows performed at Townhall 1873 during July and August. Its annual fair, held every Labour Day weekend, has been running for over 150 years. There are also golf courses, both public and private. Other attractions in Port Perry and surrounding area include the Great Blue Heron Charity Casino, Scugog Memorial Library (featuring the Kent Farndale Art Gallery), the Scugog Shores Historical Museum and the Town Hall 1873 Centre for the Performing Arts.
At many local farms, visitors may pick their own seasonal fruit (strawberries, raspberries, apples). In the summer, bass tournaments and lakeside activities are also featured.
The Lake Scugog shoreline offers two popular lakeside parks, Palmer and Birdseye. There are active fishing seasons, both winter and summer. In the winter months, Lake Scugog is dotted with ice-fishing huts and is a destination for ice fishermen and snowmobilers.