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Travel: The Best of Sag Harbor, New York

Updated on February 6, 2015
lawdoctorlee profile image

Ms.Treadwell is a licensed attorney and the author of "How Do Hurricane Katrina's Winds Blow: Racism in 21st Century New Orleans."

Sunrise in Sag Harbor

Peaceful sailboats dot the bay a short walk from the Sag Harbor Inn.
Peaceful sailboats dot the bay a short walk from the Sag Harbor Inn. | Source

We moved from Yonkers to what New Yorkers call “the island” when I was ten years old. Some of my favorite memories were during my years in Long Island. At 16-years old, I fell in love for the first time with Darryl, the “boy-next-door.” He grew up “out East” and told me stories of his hometown, Sag Harbor and the nearby Hamptons. His stories about that area of Long Island were mesmerizing for me; and I longed to visit the tiny town for many years.

Although I moved away from Long Island when I was 21 years old, I came home for regular visits since my mother and family lived in Suffolk County. Still, I always thought about visiting Sag Harbor but could never bring myself to visit, knowing it would remind me of Darryl and the heartbreak of a broken engagement because of youthful immaturity.

More than two decades later, I returned to Long Island to resettle. Naturally, I found a lot had changed. Still, I heard that "out east" was quieter and still rustic compared to central Long Island. So, one day, I decided to just take a local road trip with no real plan for the day. As I drove east on Montauk Highway, I saw a sign that said “Sag Harbor”; and, upon an emotional stirring of my heart, I took an immediate left in the direction of the town, not knowing the area at all.

The Windmill at Long Wharf


A graceful swan


The History of Sag Harbor

The size of Sag Harbor impressed me, perhaps it was because I never realized how tiny the village is. According to the U.S. Census, the population of the town is approximately 2,300. Still, although Sag Harbor is less than two square miles, it has so much to offer and was the perfect afternoon getaway for me. As I drove over the quaint bridge that connects Sag Harbor to North Haven, I immediately had a sense that I was traveling back in time.

The incorporated village is situated in Eastern Long Island and spread across the towns of East Hampton and Southampton. Presently referred to as a writing colony, it is the birthplace of poet George Sterling and was the residence of author John Steinbeck until his death in 1968. Sag Harbor is mentioned in the classic novel Moby Dick.

At the end of the bridge, to my left, was the historical wharf, an immaculate port dotted with peaceful sailboats in contrast to the neighboring, multi-million dollar yachts. The port of Sag Harbor was founded in 1707; and, according to the Sag Harbor Historical Society, in "1789, when George Washington approved the creation of Sag Harbor as a Port of Entry for the newly formed United States, the village had more square rigged vessels engaged in commerce than the Port of New York." Important military action occurred in Sag Harbor during the American Revolution and the War of 1812.

To my right was the historic Main Street with The American Hotel in plain sight. The hotel was opened in 1877 by Addison Youngs, a farmer, and his father-in-law, Captain William Freeman, a whaler. It was one of the first Long Island hotels to have modern conveniences of electric lights, steam heating, and indoor plumbing. Darryl often spoke about Main Street's 4th of July parades and his participation as a boy scout.

The location of the village sparked a successful whaling industry. Whales were harvested for their oil; and so it is fair to say that it was an oil port. The whaling industry peaked around the 1840s. Today, the wharf is home to festivals during the year and the occasional fisherman. A graceful windmill posited nearby beckons visitors to the small beach.

I found a parking spot on the wharf; and I entered The Dock House to eat the most delicious fried oysters I have ever tasted, enjoyed the gentle bay breeze, and took some photos of the graceful swans that ducked in, around, and about the boats. After a relaxed sigh, I thought to myself, "ah, this is the life."

The American Hotel in Sag Harbor

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Must See Attractions in Sag Harbor

  • Long Wharf
  • The Windmill
  • Mashashimuet Park
  • A performance at Baystreet Theater
  • B. Smith's Restaurant
  • The American Hotel

Sag Harbor Cinema

The theater was originally a vaudeville stage and host to burlesque shows. Later, silent films and then talking movies were shown. The single screen theater shows about 75 films per year.
The theater was originally a vaudeville stage and host to burlesque shows. Later, silent films and then talking movies were shown. The single screen theater shows about 75 films per year. | Source

Things to Do in Sag Harbor

Sag Harbor has it all, at least for me, because I am a bit of a history buff and a nature lover. It is a sparkling jewel in Long Island. Historical landmarks include Main Street, which boasts a number of restaurants, including the famous B. Smith's. I stopped for ice cream and then into the old "Five and Dime" to pick up postcards and trinkets. My walking tour included passing by the Whaler’s Church; the old burial ground; the Umbrella House, which housed British troops during the American Revolution; and the Masonic Lodge, which houses the whaling museum.

Nearby, I came across St. Andrew's Roman Catholic Church. Memories have a funny way of creeping into the mind. I remembered Darryl's stories about attending St. Andrew's school and his days as an altar boy. St. Andrew's was constructed in the mid-1800s and was completed in 1872. With its share of gorgeous stained-glass windows, St. Andrew's has a Gothic-style marble altar, which was built in Italy in 1922, from a combination of many different types of colorful Italian marble. The prosperity of Sag Harbor as a whaling town is reflected in the relative grandeur of this church and in its distinctive features. A beautiful pipe organ sits in a loft over the entrance to St. Andrew's. And I recall a fleeting thought, "this beautiful, white church with its graceful steeple is the quintessential wedding church."

I enjoyed a stroll through Mashashimuet Park and Otter Pond, which offer a place to relax, play, or fish. The nature preserves are home to a number of mammals including fox, mink, chipmunks, weasels, muskrats, and deer. The bays and rivers and the Sound are rich with reptiles, fish, bottle-nosed dolphins and porpoises. And though it’s an easy drive to some of Long Island’s best vineyards, I spent so much time in Sag Harbor, I was unable to fit in a wine tasting.

Places to Stay in Sag Harbor

The American Hotel
Sag Harbor Inn
Harborwoods Guest House

Liza & Darryl's Wedding

The bridal party looks on as my husband and I exchange a post-ceremony kiss in front of St. Andrew's Roman Catholic Church, 122 Division Street, Sag Harbor.
The bridal party looks on as my husband and I exchange a post-ceremony kiss in front of St. Andrew's Roman Catholic Church, 122 Division Street, Sag Harbor. | Source

Life is funny.

Life is funny; I mean, really funny. It was around the time of this day trip that Darryl and I reconnected. He was in the army and stationed in Germany. He was taken aback about my visit to Sag Harbor and my personal recollections of our teenage conversations. After dozens more phone calls (ok, maybe more than dozens), and at his invitation, I took a chance and set off across "The Great Pond" to visit him. Before we knew it, we were in love again; and I traveled several times to Europe for months at a time. When the army transferred Darryl to Texas, I packed up and joined him. A tour in Afghanistan had Darryl away for nearly a year but shortly after he returned, we were engaged again to be married.

It was not hard to decide where that wedding would take place. It had to be in Sag Harbor. So there we were planning a wedding at St. Andrew's: the church of his youth, the church that formed his values, and for me, "the quintessential wedding church with the graceful steeple." We applied for our marriage license at Southampton Town Hall, a short distance from the village of Sag Harbor. We were married the Friday of Labor Day Weekend, the busiest weekend of the year for the "East End" given the idyllic weather. We were blessed that our family and friends braved the traffic to be there on time, although I kept them waiting. I entered that breathtakingly beautiful church with the greatest sense of calm and happiness I had known in years; and I could not take my eyes off of Darryl, stoic in his full-dress military uniform.

We included a stay in Sag Harbor during our Long Island honeymoon, enjoyed a few cocktails and live music at B. Smith's and a nostalgic overnight at the Sag Harbor Inn. We strolled the wharf during the evening hours serenaded by the lights of the boats that dotted the bay and the twinkling of the stars which shone in the sky. We savored our morning coffee at a super-cool cafe called Sagtown Coffee; and I decided on a flaky butter croissant despite the wide variety of fresh pastries available there. Honestly, I never wanted to leave.

One of the Most Unique Places

I have traveled throughout Europe and the United States; so I do not say this lightly: Sag Harbor is one of the most unique places I've ever been. Sag Harbor rises to the challenge of giving one the sense of going back in time and providing every modern convenience: it is "old-world-meets-new-world." It is a place to get away from it all, a place to get back to yourself, and a place to find a new you.

Visited Sag Harbor? Give this town a rating!

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By Liza Lugo, J.D.

(c) 2014. All Rights Reserved.

Ms. Lugo retains exclusive copyright and publishing rights to all of her articles and photos by her located on Hub Pages. Portions of articles or entire content of any of these articles may not be used without the author's express written consent.Persons plagiarizing or using content without authorization may be subject to legal action.

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Submit a Comment
  • lawdoctorlee profile imageAUTHOR

    Liza Treadwell Esq aka Liza Lugo JD 

    4 years ago from New York, NY

    AliciaC, thank you so much for taking the time to read this hub and for your encouraging comments. I hope that one day you will have the opportunity to visit Sag Harbor. Blessings to you & yours.

  • AliciaC profile image

    Linda Crampton 

    4 years ago from British Columbia, Canada

    This is an interesting and enjoyable hub with a beautiful ending! It was a pleasant surprise to discover that you and Darryl reconnected. Thanks for sharing the information about Sag Harbor. It sounds like a place that I would enjoy exploring.


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