You’ll find a slice of Americana on the bay in the Village of Sag Harbor. This old whaling port spans only 2.3 square miles, but is steeped in history. With its landmarks, historic homes, museums and iconic Main Street shops and restaurants, Sag Harbor is a desirable walking village and choice destination for boaters and tourists.
Mom and pop shops, literary roots and culture dominate
A lot is packed into this small village. In the 1800s, it was one of the busiest ports in the country, and is mentioned several times in “Moby Dick.” Though it has gone through a transformation, it has maintained its small-town charm with mom and pop shops, like the Sag Harbor Variety Store. It has always had a literary history: Most notably, John Steinbeck lived and wrote “The Winter of Our Discontent” here. The Bay Street Theater and several art galleries, as well as an effort to bring back the Sag Harbor Cinema, make it a cultural hub, and a dozen restaurants and bars make it a late-night hangout for celebrities and artists alike.
Historic whaling captains’ quarters and newly constructed cottages
Featuring many finely preserved captains’ houses and whaling cottages, this village maintains a classic New England maritime feel. In the heart of the village, Greek Revival and Victorian-style homes typically command seven figures or more despite their small lots. Further away, in areas like Eastville (where wealthy African-American families summered in the mid-1900s), quaint cottages are being replaced by larger and pricier shingle-style houses.
Fine dining in this iconic hotel on Main Street offers unparalleled service and cuisine. See and be seen from the hotel’s front porch or in its elegant dining room and bar.
Sit down at the café for lunch or a freshly made juice or smoothie. Then pick up some organic groceries from the market.
Take in a show at this 300-seat playhouse at the foot of Long Wharf. Comedy shows, music and readings are offered year-round.