Marblehead is a harbour town in the old sense, a crooked tangle of lanes and clapboard houses crowded around a bay full of masts, founded in 1629 on a rocky peninsula that never offered any farmland and so turned to the sea. About twenty thousand people live here, and the streets of the Old Town are the reason to come: narrow, steep, bending at odd angles between houses built when carts were the only traffic. Salem, a bigger neighbour famous for its witch trials, lies a few kilometres to the north-west, and for riders it is the place for fuel and plentiful parking.
The riding here is slow and charming. Coming in on Route 114 or 129, you pass through suburban streets before the lanes tighten and the water appears, with views of moored yachts, sailboats and the low shape of Marblehead Neck. In the Old Town, speed limits are low, streets are narrow, parking is restricted and pedestrians are everywhere, so treat it as a place to arrive, park and walk. On a summer weekend it is crowded, and the best moments are early morning and the shoulder seasons, when the harbour is quiet and the light is crisp. Sea fog sometimes rolls in and wraps the town in grey.
The town has a proud and rebellious past. Marblehead was a fishing port that sent hundreds of boats to the Grand Banks, and its mariners were famous for toughness. During the Revolution, a regiment of local fishermen under John Glover served as the boatmen who carried Washington's army across the Delaware on Christmas night 1776, and the town claims to be a birthplace of the American Navy because a schooner from its harbour was one of the first armed vessels commissioned by Washington. In Abbot Hall, a painting called The Spirit of '76, showing a fife and drum trio, hangs on public view. Fort Sewall, a small stone fort at the harbour mouth, offers a grassy spot to sit and watch the boats.
The harbour is one of the great yachting centres on the east coast, and the annual Race Week in July fills the water with sails. The coast beyond is rocky, with tide pools, gulls and the smell of seaweed and salt, and in the evening the light turns the clapboard houses gold. Old Burial Hill, with its slate gravestones dating back centuries, is a quiet place for a walk.
Fill the tank in Salem or Swampscott, since fuel in the Old Town is hard to find, and carry a lock if you leave the bike. Allow time to wander.