Most people arrive in Greenwich by train and think of hedge funds, but for a rider it is the doorstep of a road with a real pedigree. The Merritt Parkway begins near the New York line here, and it is one of the most beautiful and eccentric roads in America. Built in the 1930s and named for Schuyler Merritt, the Stamford congressman who championed it, the parkway was designed as a garden road, not a freeway, with planted verges, gentle curves and a long run of bridges, each of which has its own Art Deco design. There are dozens of them, and no two match.
Greenwich itself is a wealthy town on the Sound, with a handsome shopping street, the Bruce Museum, and enough big houses and old stone walls to keep the neighbors in conversation. It is not a place to hunt for bargains, but it does supply fuel, coffee and food. Cos Cob, a short distance east, was the seat of an early American art colony, and the old harbor has a few authentic corners. The shoreline is mostly private, so expect to see Long Island Sound through gaps rather than from a promenade.
Riding the Merritt is a different pleasure from anywhere else in the region. There are no trucks, because commercial vehicles are banned, and the lanes are narrow and the old-style entrance ramps short, so you need to keep your eyes open and your throttle civilized. There are almost no shoulders, which means any breakdown gets awkward quickly, so check tyres and fuel before you start. Early on a weekend morning, with low light through the trees, it is lovely; at the Friday rush hour it is a slow-moving queue that nobody enjoys.
The best seasons are spring, when the dogwoods and cherries bloom, and mid-October. Traffic is thinner on Sundays than any other day. There are no services on the parkway itself, so top up in Greenwich or Stamford beforehand, and plan on leaving at an exit if you need a coffee, because the old rest areas are long gone. It is a road best savored slowly, with attention to the bridges.