A Weekend in Sag Harbor, NY

One sunny Labor Day weekend, we set out from NYC on the Hampton Jitney for a couple’s weekend getaway to Sag Harbor. It had the charm of an old whaling port that has been transformed into a hangout overflowing with the casual sophistication of the Hamptons. Where once Indians would set out on whaling boats out to sea, or merchant ships from all over the world would come to dock, now sailing boats and million-dollar yachts float in the harbor.

It’s relaxing to hang out along Main Street and by the water, however my boyfriend wanted to get a drink at the iconic American hotel, do

After settling into our AirBnB we headed to Main Street, getting some visitors information at the Windmill first. Then we walked along Main Street, found the American hotel, and gingerly stepped inside, squinting as our eyes adjusted to the darker interior. The American Hotel was bought by a whaler in 1876, who built a bar and dining room there, calling it “The American House”. Today the beautifully restored hotel offers a high-end dining experience and an award-wining wine selection.

We “stood at the bar”, which was packed about 5 rows deep that evening….we were really more pressed against the opposite wall, with waiters patiently squeezing past us. Apparently, many had had the same idea as us. After a few minutes, we decided actually getting drinks there was something we were going to have to save for another day.

The American Hotel

Sag Harbor is not a large village, but its history runs deep in the Hamptons. We got a flyer for a self-guided walking tour of the area, which also covers a lot of history. First we grabbed some donuts and coffee at Grindstone Donuts [7A Main Street, (631) 808-3370] which has wonderful scratch made donuts (my favorite was one filled with homemade blueberry jam).

Blueberry jam filled, and cinnamon sugar donuts from Grindstone Donuts

Sag Harbor Walking Tour

From the windmill you can go straight down Main street, which has most of the restaurants, shops and stops, all the way down to the Whaling Museum. To truly explore Sag Harbor however, we used our self-guided walking tour to roam around a little and learn a few things. The windmill itself is located on the Long Wharf, which since 1771 has been Sag Harbor’s hub. In its whaling heyday in the early 19th century ships were lined six deep preparing for voyages to sea which could last 6 months or more. After the whaling trade declined, this became an international port.

We hung a left onto Bay Street to check out the marina.  There is a small and relaxed beach on Bay street called, Haven’s Beach, which might be a pleasant stop for the afternoon.  We were hungry so we grabbed an excellent lunch of the best tuna burgers I’ve ever had at The Dockside Bar and Grill [26 Bay Street, (631) 725-7100]. 

We went back up Bay Street then to take the walk down Main Street and make a right on Madison to the Stanton House & Hope House, the prior residences of Admiral Stanton who took a historic visit to Japan opening up the east to the west, and Benjamin Franklin Hope who was a skilled clockmaker.  Both houses were built in the mid 19th century and are archetypal examples of early Greek Revival and Victorian architecture.    Turning back to Main Street and along Garden Street is the Custom House, which has been restored by the Society for the Preservation of Long Island Antiquities and is open to the public.  It is furnished faithfully to the period often with original pieces.  Turning back along Union Street you will find the Old Whaler’s Church, erected as a monument to the town’s whaling prosperity and it is considered the best example of Egyptian Revival style in the U.S. A point of interest is the decoration of blubber spade motifs along the roofline.  Going back up towards the water along Division Street, you will find the location of the Bulova Watchcase factory, which played a major role in the industrial revival of Sag Harbor in the early 20th century.  Right now the building is being converted into condominiums.  These are just a few of the 43 historical sites listed in the Sag Harbor Historical Societies’ self-guided walking tour.

Sunset at Sag Harbor

For us, it was time to get changed and go out to dinner at The Beacon [8 West Water Street, {631) 725-7088].  We had early reservations but couldn’t snag a seat on the outdoor patio which would have been nice.  Their menu consists of “Sunset Dinners”.  We ordered the pork chop Milanese with roasted tomatoes and blackened local fish with citrus beurre blanc and roasted beets, which were excellent. We finished just in time to catch the sunset on our way out, stopping for a minute at the bar where we could enjoy the view over the marina.

Sunset view from The Beacon restaurant

If you plan ahead (since they tend to be booked, especially in the summer) there are also boat charters and sunset cruises you can take, like those offered by American Beauty Cruises.

The next day had a more relaxed pace.  After breakfast at our AirBnB my friend went for a run along Ferry Road to Foster Memorial Beach and back, while I hung out at Sag Harbor Books and got a book about the Hamptons written by Dan Rattiner of Dan’s Papers.  The bookstore is great for browsing and I spent a quiet hour there.  Then we met up and walked up and down Main Street some more.  The sidewalk was full of people, along with some who appeared to be local residents. One woman was floating by hand-in-hand with her daughter, both wearing full-length, romantic pink tulle ball gowns which were adorned with fabric flowers, creations which we discovered can be bought for upwards of $500 at one of Sag Harbor’s small boutique shops. In terms of fashion, it looked like white pants were the thing to wear. Almost everyone we passed by (both men and women) had white pants on.  I was glad I had brought my white capris pants and sandals with my on our trip, it was my standard outfit with a nice top.  My friend also had white cotton pants and a sharp shirt on.  We blended right in, we thought. 

We walked by a charming market called Provisions, had brunch at a sidewalk café, and ate frozen yogurt at Buddhaberry [125 Main Street].  They offer only vegan frozen yogurt and there is an entire wall of all sorts of toppings like chocolate chips and sprinkles, where customers help themselves build the perfect frozen yogurt.  Soon it was dusk, and the streets became more crowded with people stepping out for dinner and drinks.

Sag Harbor Movie Theatre

Sag Harbor Movie Theatre

At 90 Main Street is the well-known Sag Harbor Movie Theatre, which was closed down after a fire but has thankfully been fully restored and is now operational.  This would be a great place to catch a movie before or after dinner, if your didn’t feel like doing all that walking up and down Main Street.

We had reservations for dinner at Lulu’s [126 Main Street, (631) 725-0900] but there was still time before dinner and a brief rain storm was brewing, so our final stop was to check out the The Sag Harbor Whaling Museum.

Scrimshaw (pictures etched on whale bones and teeth) at the Whaling Museum

Sag Harbor Whaling Museum

This was an unexpectedly fun place to hide out from the rain.  We watched a short movie on what a typical experience of a whaler on a whale boat might be like (it was a little gruesome), and then we walked through the museum looking at centuries-old maps, artifacts, and things like the typical medical bag of a doctor back in those days.  There was scrimshaw, whaling hooks and spears, and the like.  It took me back to another time, I got a sense of what it might have been like living in the salty whale port that was Sag Harbor at its beginning. 

Dinner at Lulu’s was good, if somewhat standard, bistro fare. When we were done with dinner it just seems like it was too early to call it a night.  It might be quiet here during the year, but on Labor Day weekend everyone was out – it had the air of a night out on a coastal town in the Mediterranean.  We decided to get drinks at The Page [63 Main Street, (631) 725-1810] – so we got our drinks at the bar in after all!

Sag Harbor may be an upscale, Hamptons hangout now, but is very welcoming to all.  Just as throughout its history it has housed people from all walks of life and from all over the world, today it carries on that tradition in true American spirit.

Date of trip:  September 2019

Top Ten Things to Do

  1. The American Hotel
  2. Sag Harbor Whaling Museum
  3. Grindstone Coffee
  4. Sag Harbor Book Store
  5. Provisions and Buddhaberry
  6. Chamber of Commerce Windmill
  7. Sag Harbor Walking Tour
  8. Marina and Dockside Bar and Grill
  9. Sag Harbor Movie Theatre
  10. Sunset Cruise

Published by Irena Springer

I am a travel blogger who loves to make the most out of each and every trip.

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