The oldest of the Hamptons’ villages is Southampton, a pristine and deceptively simple-looking town attracting a high quotient of socialites and the nouveau riche. The downtown is just a few blocks long, but it’s lined with leafy trees, posh boutiques, and expensive cars—Jaguars are especially well represented. All around town are winding wooded lanes dotted with splashy second homes, most of which are protected from prying eyes by tall privacy hedges.

Settled in 1640, Southampton was first called Conscience Point; its name was later changed to honor the Earl of Southampton. The town centers on the intersection of Main Street and Job’s Lane. Walking maps and brochures can be picked up at the Southampton Chamber of Commerce (76 Main St., 631/283-0402, www.southamptonchamber.com, 10 a.m.–4 p.m. Mon.–Fri., 11 a.m.–3 p.m. Sat.–Sun.).

Beaches

Southampton’s main public beach is Coopers Beach (off Cooper Neck Lane, 631/283-0247, full facilities including concession, bathhouse, chair and umbrella rental, $40 a day parking fee), at the end of Cooper Neck Lane.

No parking permit is required at the often uncrowded Old Town Beach, at the end of Old Town Road. There are only about 30 parking spaces, however, and no facilities.