Driving north from East Hampton along Route 114, through lush and fertile farm country, you’ll soon come to the old whaling port of Sag Harbor. During its heyday, Sag Harbor was a bustling and bawdy commercial town, and some of that lively atmosphere—so different from the elegance of the Hamptons—still lingers.
Sag Harbor is a good town to explore on foot. Lower Main Street is filled with shops and restaurants, while upper Main and the side streets hold dozens of 19th-century homes and huge old trees. At the foot of Main Street is the weather-beaten 1,000-foot Long Wharf, which offers close-up views of the harbor.
Plentiful parking is available near the waterfront, especially between Main and Meadow Streets. Traffic usually doesn’t get quite as congested here as it does in the Hamptons, but it can still be daunting.
In summer, the Sag Harbor Chamber of Commerce (55 Main St., 631/725-0011, www.sagharborchamber.com) runs a visitors information center (9 a.m.–5 p.m. daily July–Aug.) in the old windmill at the entrance to Long Wharf.
The Society for the Preservation of Long Island Antiquities (631/692-4664, www.splia.org) publishes a succinct walking-tour map of historic Sag Harbor sites; look for it inside their brochure on the Custom House.
© Avalon Travel and Sascha Zuger from Moon New York State, 5th Edition