Drive past the ocean-facing towns of Southampton, Water Mill, and Bridgehampton and you'll find the beauty of the bay “north of the highway”: Sag Harbor.
Main Street is a picture-perfect vision of what an ideal town should be: leisurely, family friendly, featuring unique boutiques, and top restaurants. Add to that the cultural caché of the Bay Street Theatre with the celebrity caché American Hotel and you have a formula for the good life.
Living in Sag Harbor
On the northern edge of the South Fork, looking out onto scenic waters dotted with yachts, Sag Harbor is a charming old port village with plenty of character. Its thriving history is evident in the carefully preserved architecture that lines Main Street. However, this is no museum piece and the village sustains a vibrant and varied social scene. Stylish bars and restaurants overlooking the harbor make elegant spots for cocktails at sunset and the village hosts a plethora of cultural attractions, most notably at the well-regarded Bay Street Theater.
Sag Harbor real estate
Sag Harbor provides luxurious and elegant properties for rent or sale. Stunning waterfront homes give both direct bay access and all the advantages of close proximity to the restaurants and theaters of the village. Enjoy wonderful sunset views from waterside decks and private pools. Sag Harbor real estate includes some stunning upscale contemporary architecture, where designs seamlessly link interior and exterior spaces — perfect for summer entertaining. In the village itself, traditional architecture predominates, with quaint clapboard cottages, elegant, Greek Revival homes and well-proportioned historic captain’s houses all providing summer homes that offer you your own slice of Sag Harbor’s prestigious history.
Sag Harbor history
The town, founded in 1707, had the advantage of its harbor being deep enough to accommodate the growing number of international ships that were plying trading routes to the region. The port played an important role in the Revolutionary War, when the British garrisoned troops here. During the War of 1812, British Navy ships were stationed nearby at Gardiners Island when they unsuccessfully attacked Sag Harbor in July 1813.
In the 19th century Sag Harbor became a thriving whaling port, bringing more international vessels, merchants, and fame — it’s even mentioned in Herman Melville’s Moby Dick. Many of the village’s landmark buildings date from this time, including the Old Whalers’ Church, Greek Revival mansions and Victorian-style homes. Later, as whaling declined, Sag Harbor was a major transport hub for all forms of industrial merchandise before becoming a popular summer destination.
Sag Harbor things to do
One of the showpiece buildings on Sag Harbor’s Main Street makes a fitting home for the Sag Harbor Whaling & Historical Museum. The building, a grand, pristine white Greek Revival structure fronted by a portico with ornate Corinthian columns, was built in 1845 as the home of Benjamin Huntting II, a wealthy whaling ship owner. Later it was a Masonic Lodge (they still use an upper floor), before becoming a museum. The building is listed on the National Register of Historic Places, and its exhibits offer a comprehensive history of whaling through the extensive range of whaling artefacts.
Nearby, a simpler building also harks back to Sag Harbor’s heyday. The Custom House, which dates from 1789 when Sag Harbor became a US port of entry, was the home of the port’s first Custom Master. Custom House is now a museum that recounts the life of the Custom Master Henry Packer Dering and his family.
Today boating in Sag Harbor is more likely to be on leisure crafts; its waterfront is busy with boats, a marina, historic yacht clubs and charters. Sag Harbor Charters operates tours of the bay, while Sailacat offers private catamaran yacht charters, taking you out to explore the nearby bays and islands.
You’ll find more extensive beaches beyond Sag Harbor, but Haven’s Beach, only a five-minute drive from the town center, is known for its calm waters. This area is excellent for families, walkers and those who just want to sit and watch the boats go by.
Sag Harbor restaurants
Sag Harbor offers a sophisticated, varied dining scene. There are over 20 restaurants within the village, mostly focused on lively Main Street and the harborside. The American Hotel, which dates from 1846, has long been a centerpiece of Main Street. The restaurant combines French influences and local specialties. Expect lobster bisque, foie gras, oysters, or tuna steak served with a chive beurre blanc sauce.
For an unsurpassed bayside location, perfectly situated for sunset, the firm favorite is Beacon. Only open in summer, it produces a seasonal menu, which changes from year to year. Look for fresh flavors, seafood and some trademark dishes, such as halibut baked in parchment. Looking out over the yachts of Sag Harbor is the Dockside Bar & Grill, an informal seafood joint, perfect for grabbing a quick sandwich or fresh fish tacos.
There’s more than enough to tempt you within the small network of streets by the harbor, but if you venture just a little farther out, you’ll be rewarded with a real gem in the Sag Harbor dining scene. Estia’s Little Kitchen has earned a reputation with those in the know for its varied menu, which includes healthy, light takes on Mexican dishes, including delicious Crab tostadas, shrimp taquitos, and adobe pork nachos, often incorporating ingredients from the restaurant’s own garden.
Sag Harbor nightlife
Sag Harbor can claim a couple of the East End’s most historic cultural destinations. Bay Street Theater, a non-profit venue right by Long Wharf on the bay, has developed a formidable reputation for its works, many of which have transferred to Broadway. Inland stands the much-loved Art Deco single-screen Sag Harbor Cinema, with iconic its “Sag Harbor” sign lighting up Main Street.
For a drink, the bar at the American Hotel is always a classic spot to start the evening with a cocktail or a glass from their excellent wine list. A low-key watering hole, The Corner Bar makes a good stop for a beer. Night owls head to Murf’s Backstreet Tavern, a tiny place with regular live music, that’s open until 4am.
Like St. Barth in the U.S.
"In Sag Harbor you can find yachts in the harbor, avant garde art galleries, local cinema and a grocery store on Main Street. Sag Harbor is one of the few towns where you can stroll and shop at night."
What's In The Area: Sag Harbor
Local tips and information for going out in the Sag Harbor from The Corcoran Group. Explore dining, shopping and nightlife.All Sag Harbor tips