The most charming bike city in North America may well be Montreal, where Old World flair meets cycle-friendly infrastructure. After checking in to the Gingerbread Manor Bed and Breakfast, head to Cycle Pop for bike rentals. Pick up route maps at Vélo Québec, then snake through the city's bike-route network and climb little Mont-Royale, a 763-foot urban mountain. Stop at the Marché Atwater farmers' market, then make your way northeast toward the cobblestone streets of Old Port. Day two: Pack a picnic from Premiére Moisson and drive 45 minutes north (or take the commuter train) to Le P'tit Train du Nord bike path, a 135-mile stretch of transformed rail trail that transects the Laurentian Mountains.
Two nights at the Gingerbread Manor (gingerbreadmanor.com): US$220. Two 48-hour bike rentals (cyclepop.ca): US$70. Map (velo.qc.ca): US$6. Farmers' market lunch (marche-atwater.com): US$25. Train fare for two to St. Jerome (amt.qc.ca): US$40. Gelato from Havre Aux Glaces (514-278-8696): US$7. Picnic lunch and bottle of wine (premieremoisson.com): US$40. Total: US$408.