In the Oshawa & Durham area east of Toronto, there are several key retail districts, where you can find pretty well anything you’re looking for:

Pickering

Pickering’s shopping district lies along Kingston Rd, and nowadays consists of a seemingly non-stop sequence of malls and plazas, north of the 401.

Shopping in Ajax Billage

Ajax

Ajax is home to Durham’s premier shopping area, with many shops along Kingston Rd, and over 92,900 sq. metres (one million sq. ft.) of retail space. Historic Pickering Village has the appeal of a quaint 19th century Quaker settlement. Ajax has a collection of malls and plazas along Harwood Ave between Bayly St and Kingston Rd, north of the 401.

Whitby's Four Corners shopping area

Whitby

Whitby’s shopping district is centred around “The Four Corners” where Dundas Street East meets Brock St, which also has some older period architecture.

There is a second historical shopping district in Brooklin, at the intersection of highway 7 & 12, a few km north of Whitby. There is also a Farmers Market each Saturday during the summer.

Oshawa

Shopping at Oshawa's Four Corners

Oshawa has a vibrant shopping district is centred along Bond & King Streets.
There are a mix of older heritage buildings and modern retail facilities, with specialty stores and fine restaurants, as well as
a seasonal Farmers’ Market at the Queen’s Market Square, in the heart of the city.
The downtown also is home to the Robert McLauglin Gallery, the Canadian Automotive Museum, and has a large collection of historical murals.

Bowmanville

Historic downtown Bowmanville has recently become more pedestrian-friendly with interlocking brick sidewalks and historical period lighting, and implemented two hours free parking at municipal lots. Shoppers can find everything from antiques to designer clothing along and adjoining King Street.

Cobourg

Downtown Cobourg, the economic hub of Northumberland County, has picturesque streetscapes and well-preserved architecture surrounding historic Victoria Hall, and is home to over 250 businesses. Two blocks up from the marina, is an eclectic mix of specialty retail shops & boutiques, services, restaurants, pubs and cafes. Saturdays also has a Farmers’ Market.

Trenton

Dundas Street is the major shopping area of the town, and is close to the marinas and Trent Canal.

Belleville

Downtown Belleville, adjacent to the Moira River near the Bay of Quinte, has old brick buildings of a Victorian city centre. Front Street is the City’s main street, but there is a lot happening on Pinnacle and Dundas Streets and other side streets. It is predominated by small retail shops, professional services, entertainment services, and functions as the region’s administrative/governmental centre.

Downtown Port Perry

The pristine Victorian architecture and historic buildings, overlooking the shores Lake Scugog, gives the downtown unique charm. There is an eclectic mix of business including retail merchants, restaurants, attractions, financial institutions and professional services.