Breckenridge's quaint main street could be a painting of the mountain resort of your dreams. The oldest and largest town in Colorado's famous Summit County started out, like many, as a mining town, and locals aren't about to forget it — the 250-plus buildings on the National Historic Register attest to that. That historic downtown district is packed with shops and local restaurants. Four mountain peaks make up Breckenridge's popular ski resort, and year-round recreation can be had on its surrounding peaks and trails.