Marblehead is at its most appealing in summer (June–September) and early autumn (October). Summer brings the full harbour scene — regattas, day-sailors, and the town animated with seasonal visitors — while October has brilliant foliage, crisp air, and quieter streets. The Marblehead Race Week in late July is one of the oldest sailing regattas in the country and draws serious competitors from the northeast. Winter is cold and the town is quiet; many seasonal restaurants close.