Sag Harbor: Historic Whaling Port a South Fork Treasure

Few places on Long Island’s East End deliver the area’s one-of-a-kind blend of old-money opulence, small-town charm, and bucolic serenity like Sag Harbor does. This historic South Fork village is considered part of both East Hampton and Southampton, but it stands on its own as one of the finest examples of everything there is to love about Long Island. 

Settled in the early 18th century, Sag Harbor quickly grew into an important whaling center and seaport, serving as a theater of war during the American Revolution, and eventually becoming the first port of entry in the state of New York, all before 1800. 

“Sag Harbor is an authentic charming maritime community that has existed here in this beautiful location in one form or another since the early 1700s,” Town Mayor James Larocca tells us, “and to a remarkable degree [it] has been able to maintain and hang onto much of the charm of that early era.” 

The town got its own Long Island Rail Road branch in 1870, inspiring both a transition to manufacturing and a boom in tourism, the latter of which is the primary industry in Sag Harbor today. 

If you’re interested in supporting that industry in the near future, consider the following: 

Charming History

The cool thing about Sag Harbor is that it wears its history on its sleeve more prominently than perhaps any other town in the South Fork.

It has notable landmarks like the Custom House (192 Main St., 631-692-4664) and The Sag Harbor Whaling and Historical Museum (200 Main St., 631-725-0770, www.sagharborwhalingmuseum.org), two historic buildings dedicated to sharing the town’s rich history. 

“Sag Harbor, in terms of total number of voyages made, was the sixth largest whaling fleet in America from 1760 to the 1870s and made roughly 750 voyages during that time,” whaling museum Director Richard Doctorow tells us. “[The whaling industry] impacted the daily lives of everyone in the village and the surrounding communities.”

The museum has four rooms of standing exhibits and offers special exhibits in its main gallery, which rotate throughout the year. This September their special exhibit is Her Story: A Celebration of Sag Harbor Women 1800-1970.

But what makes Sag Harbor’s appreciation and acknowledgement of its own history truly stand out is its dedication to preserving its small port town feel.

Take a walk down Main Street and enjoy all the most romantic parts of that bygone American era where every community had its own colorful personality and mom and pop shops were the norm.

Highlights include The Wharf Shop (69a Main St., 631-725-0240 www.wharfshop.com), a classic toy store, Sag Harbor Variety Store (114 Main St., 631-757-9706 www.sagharborvariety.com), the local Five and Dime, and Schiavoni’s Market (48 Main St., 631-725-0366, www.schiavonismkt.com), a 90-year-old family-owned market offering specialty and gourmet foods and various locally made products. 

“We maintain [the town] carefully, with effort, and with difficulty,” Mayor Larocca says of the local governments efforts to preserve Sag Harbor’s small-town charm. “We’re not anti development, we’re not anti commerce, or any of those things, but we don’t get to enjoy a waterfront like this without some considerable effort and investment.”

A Rich Multicultural Heritage

Another aspect of Sag Harbor’s history that locals are committed to preserving is that of their African American, Native American, and other minority communities, all of whom play a crucial role in the telling of the Sag Harbor story.

Perhaps the best way to learn about and appreciate these essential pieces of the town’s past and present is at the Eastville Community Historical Society (139 Hampton St., 631-725-4711, www.eastvillehistorical.org). They offer an ever-changing series of exhibits dedicated to preserving and promoting the unique history of their multicultural community.      

Executive Director and Chief Curator Georgette Grier-Key says that visitors to the Historical Society have a chance to “learn the history of the thriving community of multiethnic people that came before us…that includes others like women and the BIPOC [Black and Indigenous people of color] community.” 

“We think history is so far away from us,” Grier-Key says. “It happened right here in this spot.” 

Bayside Beaches

The typical sandy shores frequented by Hamptons tourists is one that meets the Atlantic Ocean head-on, which is what makes the beach experience in Sag Harbor something of a curveball for the uninitiated.

Local sand-and-sun destinations like Foster Memorial Beach (1000 Long Beach Rd., 631-728-8585) and Havens Beach (Havens Beach Rd., 631-725-0222) reside along either Sag Harbor Bay or Noyack Bay, which means they’re a bit more rocky, a lot more calm, and the swimming is much more relaxing.

East-End Eden

For more outdoor enjoyment, check out Sag Harbor’s first new waterfront park in over 100 years: John Steinbeck Waterfront Park (www.johnsteinbeckwaterfrontpark.org), named after the iconic American author who spent the later years of his life, and wrote both Travels with Charley and The Winter of Our Discontent, in Sag Harbor. 

The park offers 1.25 acres of peaceful greenery and serene shores. There are picnic tables and benches, both great places to relax and take in a beautiful day with a good book.

Eclectic Arts and Entertainment

You can find hip galleries and charming theaters all throughout the Hamptons, but Sag Harbor’s relatively offbeat personality lends itself to a selection of galleries, theaters, and more that are among the hippest and most charming of all. 

Sag Harbor Cinema (90 Main St., 631-725-0010, www.sagharborcinema.org) is the building with the iconic art deco neon sign illuminating its façade. The historic theater burned down in 2016, but has since been fully restored and currently screens current and classic films, documentaries, and more.

“[The fire] became the engine that made possible what we have today,” Founding Artistic Director Giulia D’Agnolo Vallan says. “It’s a beautifully renovated three-screen facility with a café at the entrance, a bar upstairs, two terraces, and complete state-of-the-art projection. It has a technical setup that allows the audience to see the films at their best, as they were intended to be seen.”

Bay Street Theater & Sag Harbor Center for the Arts (1 Bay St., 631-725-9500, www.baystreet.org) is a not-for-profit professional regional playhouse that offers productions of beloved plays and musicals as well as other unique performances.  

If you’re looking for art galleries and exhibits, start with either The Church (48 Madison Street, 631-919-5342 www.thechurchsagharbor.org) or Grenning Gallery (26 Main Street, 631-725-8469 www.grenninggallery.com). 

From Sept. 10-11, you can take part in a storied Sag Harbor tradition by attending HarborFest 2022 (Sag Harbor Marine Park, 7 Bay St.). The two-day festival includes vendors, food, beer and wine, a boat show, live music, and much more.

An Offbeat Shopping Experience

High-end designers thrive Out East, but Sag Harbor provides a decidedly different flavor with their retail offerings. Think antique and vintage rather than Armani and Versace.

Some of the bigger standouts include…

Ava’s & Around Again (1 Long Wharf St., 631-725-4067, www.avasaroundagain.com), a funky boutique and consignment shop that’s representative of all the eclectic flavors you’ll find when shopping in Sag Harbor.

Black Swan Antiques (26 Main St., 631-377-3012), an unusual antique shop offering rare and beautiful furniture, décor, and more. 

Kites of the Harbor (75 Main St., 631-725-9063), an enchantingly colorful kite shop that also has a variety of interesting toys for your kids (and you) to check out.

Any Meal You’d Like

The Village of Sag Harbor isn’t much larger than two square miles and yet you’re likely to be impressed by each of your three square meals no matter where you go. Here are our breakfast, lunch, and dinner recommendations: 

Start out at The Grindstone Coffee & Donuts (7 Main St., 631-808-3370, www.grindstonedonuts.com) where you’ll find brioche and cake donuts, sandwiches, and a drink menu containing some of the finest coffee, matcha, and espresso around.

Around lunchtime stop into Cromer’s Market (3500 Noyack Rd., 631-725-9004, www.cromersmarket.com) to get a taste of an award-winning deli and butcher shop that locals love. The fried chicken is legendary.

When you’re ready for dinner, check out The Beacon (8 W. Water St., 631-725-7088, www.beaconsagharbor.com) or Dockside Bar & Grill (26 Bay St., 631-725-7100, www.docksidesagharbor.com) for the local rendition of the kind of scenic seafood-centric waterfront dining that the Hamptons are renowned for. 

Luxurious Lodging

Unless you live on the East End, Sag Harbor is the kind of place that merits an overnight stay or two so you can really take in all it has to offer (and avoid repeated trips through the notorious South Fork summer traffic). Fortunately, there are more than a few noteworthy places to spend the night.

The American Hotel (49 Main St., 631-725-3535, www.theamericanhotel.com) is an iconic local structure that’s been giving travelers a place to rest their heads for close to 200 years. Its convenient location offers close proximity to many other attractions.

For an upscale experience, it doesn’t get better than Baron’s Cove (31 W. Water St., 844-227-6672, www.caperesorts.com). The resort was the first of its kind when it was built in the late 1950s, and the experience it offers still stands alone in many respects. 

Sag Harbor is also a fantastic place for overnight boating. Sag Harbor Village Marina (7 Bay St., 631-725-2368) offers transient slips, as well as restrooms, showers, wireless Internet, and more.

Where to Stay in Sag Harbor

The American Hotel

49 Main St., 631-725-3535, www.theamericanhotel.com

Baron’s Cove 

31 W. Water St., 844-227-6672, www.caperesorts.com

Sag Harbor Inn

45 W. Water St., 631-725-2949

Sag Harbor Village Marina 

7 Bay St., 631-725-2368, www.sagharborinn.com

Where to Dine in Sag Harbor

LT Burger

62 Main St., 631-899-4646, www.ltburger.com

Sen

23 Main St., 631-725-1774, www.senrestaurant.com

Page at 63 Main

63 Main St., 631-725-1810, www.page63main.com