Charlottetown is the capital of Prince Edward Island and the birthplace of Canadian Confederation. With around 35,000 residents, it is a small city by any measure, but it punches well above its weight in restaurants, culture, and walkability. The historic downtown is compact enough to explore on foot in an afternoon, lined with Victorian buildings in bright paint and independent shops that have somehow held off the chains.
The city calls itself "The Birthplace of Confederation" and means it. In 1864, delegates from the British North American colonies met at Province House to discuss the union that would become Canada three years later. The irony is that Prince Edward Island itself held out until 1873 before joining. Province House still stands at the centre of the city, and you can visit the room where those first talks took place.
Charlottetown's layout dates back to surveyor Samuel Holland's plan from the late 1700s. Four large squares -- Hillsborough, Connaught, Rochford, and Kings -- form the corners of a rectangle with Province House at its heart. The waterfront boardwalk runs along the harbour, busy in summer with buskers and ice cream stands. Victoria Row, a block of restaurants with patios spilling onto the closed-off street, is the social centre on warm evenings.
Summer is peak season, when the Charlottetown Festival runs at the Confederation Centre of the Arts. The musical adaptation of Anne of Green Gables has played here every summer since 1965. But Charlottetown is also pleasant in fall, when the island's famous red and gold foliage is at its best and the crowds thin out.