Captain Kidd, the pirate, is said to have buried treasure on Charles Island, off the coast of Milford, in 1699, shortly before his arrest and execution. Nobody has found it, but the legend lives on. The island is connected to the mainland at low tide by a sandbar, and you can walk across from Silver Sands State Park. Be careful: the tide comes in fast, and people get stranded every year.
Milford is one of the oldest towns in Connecticut, founded in 1639 by Puritan settlers, and its centre has a long green, old churches and houses, and a harbour where oyster boats once worked. The Wepawaug river runs through the town, with a duck pond and a waterfall near the green.
The beaches along the Milford shore are sandy and calm, with views across Long Island Sound. Silver Sands State Park has a boardwalk through the dunes and salt marsh, with birds and wildflowers.
This stop marks the end of the ride from the Taconic hills, a day of backroads through the woods and farms of the Hudson Valley, and the coast is a pleasant contrast. The final stretch follows the Merritt Parkway or I-95, both often congested.
Fuel is everywhere on the Boston Post Road. Down at the harbour, where the oyster fleet once worked, fried clams with a cold drink and the Sound turning silver at dusk make a fitting full stop to a day of Hudson Valley back roads.