Eastern Long Island is a world away from hectic New York City. Gorgeous beaches, stretches of preserved forest, idyllic farmland, and quintessentially American small town main streets all make this area a perennial attraction for the well-heeled and tourists alike.

Montauk Point Lighthouse

Montauk Point Lighthouse

Sag Harbor, NY

We used the village of Sag Harbor, NY, as a base. The town was a whaling port in its early days, but I don’t think folks here are doing too much whaling anymore–I did not see any blubber on the docks or any peg legged sailors on the brunch line.

We stayed within a short walking distance of the Sag Harbor Village District, which was bustling with out-of-towners browsing the shops and queuing up for hour-long waits on the restaurant lines. We managed to get dinner here each night, despite the long waits. We also enjoyed getting ice cream after and relaxing on a park bench along the street under the night sky.

Sag Harbor Main Street

Main Street, Sag Harbor on a busy summer night

Montauk, NY

Since I was waking up like two hours before everyone else, I drove out to Montauk, the most eastern point of New York State and site of the Montauk Point Lighthouse.  I left early enough so that would not get stuck in infamous Hamptons traffic in and around East Hampton on Route 27 (Montauk Highway).  The road leads through a couple of state parks and nature preserves that skirt the beaches on the Atlantic Ocean side of the South Fork, one being the Hither Hills State Park. At Hither Hills you can pull off the road and get a nice view of the surrounding landscape.

A few miles up the road is Montauk, an oceanfront hamlet with a string of restaurants, souvenir places, ice cream shops, and surf shops.

Montauk, NY

Montauk downtown

I drove through the town without stopping since I wanted to check out the Montauk Lighthouse first. I parked for $8 near the Lighthouse and decided not to enter the Lighthouse museum due to the extra $9 admission fee—I wanted to walk around outside anyway.

Montauk Point Lighthouse entrance

Montauk Point Lighthouse entrance

The short walk down to the beach below the Lighthouse was pleasant and I got a few good close up pictures of a butterfly.

Monarch butterfly

Monarch butterfly near Montauk Point Lighthouse

Montauk has some of the best surfing on the East Coast, I hear, and I could understand that reputation as large waves crashed against the breakers below the lighthouse grounds. From one side of the lighthouse, by the visitors center, I could see across Connecticut and Block Island with my naked eye across Long Island Sound.

Montauk Point bluffs

Bluffs west of Montauk Point

On the way back, I had an awesome seafood lunch at St. Peter’s Catch a block or two over from the Montauk main street.

Shelter Island, NY

Shelter Island is located right north of Sag Harbor, between the South and North Forks of Long Island. Though it was long inhabited by indigenous peoples, Europeans took possession of it in the early 1600s.

Shelter Island car ferry

Shelter Island car ferry

Shelter Island is actually still an island; there are no bridges to it so you have to take car ferry from either the North or South Fork. I took the South Fork ferry for a total of $17 round trip and visited the Mashomack Preserve, a 100 acre area of forest trails, marshland, grassland, and views of the Sound.

Mashomack Preserve, Shelter Island

Mashomack Preserve, Shelter Island, walkway through marsh

Mashomack Preserve

Marsh at Mashomack Preserve, Shelter Island NY

If you’re looking for a quiet hike through the woods, this park run by The Nature Conservancy is the place to go. I saw two other people on the trail the entire time I was there. Shelter Island also has a nice little downtown area with a bunch of shops and restaurants—though not as dense as Sag Harbor by any measure. I had a seafood lunch at Commander Cody’s Seafood and then found a great used book store.


While the Hamptons have a reputation for exclusivity and wealth, you don’t have to blow through your savings to experience the area. Stick to the state parks and less expensive restaurants and you’ll be fine.


  • Renting a car is really the only option here
  • Bring binoculars to get an even better view from Montauk point
  • If you’re flying, book early and fly Southwest Airlines into Islip from BWI (if coming from the DC area of course)


Shelter Island, Commander Cody’s Seafood: If you’re not paying attention, you’ll drive right by this place. It looks like a regular house. In the back, down a narrow driveway, you’ll see the restaurant. I had a fried shrimp platter and really enjoyed it.

Montauk, St. Peter’s Catch: Right off Montauk’s main strip, this place serves excellent lobster in a cool old house overlooking the town’s main baseball field. I treated myself to the lobster platter, which actually filled me up.

Sag Harbor: LT Burger: an independent burger place a la Shake Shack or Bolt Burger or BGR or (you get the hint)

Sag Harbor: Sen: an Japanese place serving sushi and sake and sashimi–you name the S. If you can get a table on a busy summer night, you’ll probably will leave satisfied but a lot lighter in the wallet. Be prepared for a wait during the summer.




Kevin is based in Washington, DC and writes about his travel adventures in the Mid-Atlantic region and around the world. Through entertaining writing and eye-catching photography, he aims to provide readers with useful information as they plan their next trips.

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