1. Toronto to Belleville

The route: If you’re driving to Belleville or Prince Edward County, forgo the monotony of the 401 and jump on Highway 2 at Port Hope. This meandering road, which offers a survey of 19th-century homes and flirts with Lake Ontario, takes you directly into downtown Belleville.
Driving time: Three hours.
Roadside attractions: Your detour begins in Port Hope, a haven for discerning antique hunters. In Cobourg, stop in at the Human Bean café (80 King St. W., 905-377-1755), which serves an expert latte and sumptuous lunches (salads, panini, samosas). In the quaint town of Colborne, the Colborne Art Gallery (51 King St. E., 905-355-1798) exhibits everything from native art to abstract canvases. Highway 2 is known as the Apple Route; before Brighton, you’ll find Cricklewood Farm (27 Grandview Rd., RR 4, 613-475-4293), where you can pick eight varieties of apples and get lost in a corn maze. The town of Brighton has a small but splendid retail strip with a couple of old-timey furniture shops: Borchert Furniture (19 Main St., 613-475-2315) and Main Street Antique Market (13 Main St., 613-475-0003). Before heading on to Trenton and Belleville, make a short detour to Presqu’ile Provincial Park (RR 4, 613-475-4324), which features hiking trails, a long beach and a historic lighthouse.

2. Toronto to Niagara Falls

The route: The QEW is nigh unavoidable up until Hamilton. Get off at Steeltown and take the 8/81 through Grimsby, Beamsville, Jordan and St. Catharines before heading up to Highway 87, where it’s one vineyard after another. Enjoy the undulations of what is arguably the most picturesque road in southern Ontario.
Driving time: Three and a half hours.
Roadside attractions: After Hamilton, you’ll need a treat. Stop in at the Beamsville Bakery & Patisserie (4966 King St., 905-563-4533) for an old-fashioned apple fritter. Carry on along 81 until you reach Ball’s Falls Conservation Area (6th Ave., Louth, 905-788-3135), a 615-acre park with two breathtaking waterfalls. Soon after, you’ll hit your first major wine outpost: Jordan. High rollers will make a beeline to the gourmet restaurant On the Twenty (3845 Main St., 905-562-5336); the budget-conscious will go across the street to Zooma Zooma (3836 Main St., 905-562-6280), which makes a mean Reuben sandwich. Take 81 through St. Catharines and north to 87. You’re now on the official Wine Route. For proof, take a quick detour off 87 and visit the Stratus Winery (2059 Niagara Stone Rd., 905-468-1806), a postmodern slab that looks more like a library than a vineyard (the wine is as innovative as the architecture). Carry on along 87 into Niagara-on-the-Lake, a Pleasantville-like hub that’s a photographer’s dream.

3. Toronto to Waterloo

The route: Take the 401 to Brampton, then resume your westward journey on Highway 7. Don’t be frightened off by the monotonous subdivisions; suburban sprawl soon gives way to small-town quaint, as 7 winds through Georgetown, Acton, Rockwood and Guelph.
Driving time: Three hours.
Roadside attractions: Georgetown’s historic strip has recently been refurbished; the highlight is McMaster Meats and Deli (110 Main St., 905-702-1274), which is not only a stellar butcher, but also has an improbably exotic frozen foods section (butter chicken, vindaloo). A trip through Rockwood is incomplete without stopping at Saunders’ Bakery (104 Main St., 519-856-9561); opened in 1914, its specialty is old-fashioned sugar doughnuts. Once back on 7, take Wellington Road 44 south to the Streetcar and Electric Railway Museum (13629 Guelph Line, Milton, 519-856-9802), which features vintage trains and trolleys galore. Moving along Highway 7, take Highway 29 north for five kilometres to Knapp’s Country Market (8066 Wellington County Rd. 124, RR 1, 519-824-4222), which offers an assortment of fresh produce, organic meats, homemade preserves and superlative cinnamon buns. If you only have time for one stop in Guelph, make it the Book Shelf (41 Quebec St., 519-821-3311), a bookstore–slash–café– slash–rep theatre and all-around hipster haunt.