N ewport was always an enigma to me. For years, I heard tales of beautiful mansions, streets of opulence, centuries of history, a very endearing grass tennis court, a music festival, and, well, sailing. Yet despite living in New York City for over a decade, I'd never made the trip up I-95 (or the Northeast Corridor line) to see this historic town. So when the invitation came from A. Lange & Söhne to join them at the Audrain Concours d'Elegance, I leaped at the opportunity. I was excited to experience the car show, but I was equally excited to see the backdrop.

The history is everywhere the moment you enter Newport, and the town offers so much that it's worth the trip regardless. Audrain just sweetens the deal. The timing, late September/early October, is smart. It's just at the tail end of the season, so you still get those beautiful summer sunsets and light, but the crowds have lessened.…