If you want to visit a quintessential village that represents the East End, then spend time in beautiful Sag Harbor. While having modern-day offerings, it still has the look and feel of a bygone era, with an old-fashioned five and dime store,a movie theater looking like something out of the 1950s, and a friendly, small-town atmosphere. Of course, it doesn’t hurt that the town is set on the water’s edge with a beautiful wharf and bridge as its background.
Once a bustling whaling center and one-time port entry for New York, this picturesque town is filled with refurbished buildings from that era, and streets are lined with homes originally built for whaling captains.
A good place to begin your Sag Harbor exploration is on Long Wharf, lovingly referred to by locals as "The Wharf". Here, a picturesque windmill does double-duty, serving as a unique background for photo opportunities as well as being the town’s information center.
Long Wharf has a short boardwalk filled with fun things to do. Here is where you’ll find famed restaurant B. Smith’s, as well as a quaint shopping "mall" with a vintage clothing store tucked inside (Around Again), and of course, there is that spectacular view of the water with gigantic and amazing yachts from around the world. At the end of the wharf, where Long Wharf, Bay Street, and Main Street intersect, sits the gem of Sag Harbor, Bay Street Theatre. This not-for-profit regional theater offers big names, plus a vast array of year-round activities for all ages, from comedies, dramas, and musicals to first-time performances of works by renowned playwrights.They also have summer kids’ camps, movie nights, family events, and their ever-popular summer gala.
Main Street is filled with a multitude of shops, galleries, and restaurants. With a nod to yesteryear, visit the Sag Harbor Variety Store, an old-fashioned five and dime where you can find anything from children’s toys to kitchen goods. Need a potato peeler? A beach towel? A hostess gift? This is the place to go! One place to stop,whether for an overnight stay or a late-night cocktail, is the not-to-be-missed American Hotel, built in 1846 during the height of the whaling era. This boutique hotel, a member of the Historic Hotels of America, offers a high-end restaurant with multiple dining areas, plus an outside seating area that overlooks the activity on Main Street. Another popular Main Street restaurant is the Zagat-rated Sen, a Japanese restaurant and Sushi bar. Just off the beaten path is a charming little Italian place called Il Cappuccino. Looking like something straight out of the movie Lady and the Tramp, this small, cozy place serves Northern Italian cuisine and is open seven nights a week.
Find out all that is going on in Sag Harbor and the surrounding areas (East Hampton,Southampton, Noyac, North Haven, and Bridgehampton) by picking up the local newspaper,The Sag Harbor Express. This award-winning newspaper began in 1859 and has reported on fantastic stories over the years, from the assassination of President Abraham Lincoln to the testing of torpedoes here for World War I! One hundred and fifty years later, the Express is contemporary, yet it still maintains the old-fashioned standards of caring about the local community. Also look for their magazine, XO,which covers recreational activities as well as the latest in holistic health.
If you like history, take a walk down the tree-lined streets to The Sag Harbor Whaling Museum, a whaling captain’s mansion from the mid-1800s. It now houses whaling tools,exhibits, scrimshaw from the period, toys, boat collections, and more. Other places to visit are the Old Whaler’s Church, listed on the National Register of Historic Places, and the first Customs House in the United States, the Old Customs House,built in 1789. There is also the Fire Department Museum, created in 1803, the oldest volunteer fire department in the state, with antique equipment on display. Checkout the town websites (listed in the informational sidebar) for an extensive list of other historical places of interest.
When you’re ready to explore outside of the village’s central area, you can get some sun at Haven’s Beach on Bay Street; the Sag Harbor Golf Course, a nine-hole course open to the public; Mashashimuet Park with a playground for the kids, tennis courts, and basketball court; or visit the nearby Channing Daughter’s Winery, which also has an interesting outdoor art collection. For more outside fun, check out the Elizabeth A. Morton National Wildlife Refuge, a wonderful way to get fresh air,with its 187 acres of forest, grasslands, and salt marsh. Another way to explore Sag Harbor is from the water’s vantage point…take a 90-minute narrated sightseeing cruise aboard the American Beauty II, which offers several cruises daily, plus a romantic sunset cruise.
With local activities, such as the annual maritime festival and lobster bake, the farmer’s markets, holiday parades, and all the other great things Sag Harbor has to offer, it is no wonder that this little slice of heaven is such a popular tourist destination.