Strolling Through Sag Harbor


As another summer Friday came and went, I decided to make the most of the day by heading out to Sag Harbor on Long Island’s East End. I haven’t been to Sag Harbor since I was a child, but the quaint and idyllic town looks just as I had remembered it.

My plan for the day was simple – to just enjoy exploring the landscape. I love going out that way because even though I haven’t actually left Long Island, I feel worlds away. The small towns out there have such charm and character and the locals are friendly and more than happy to tell you what to do while you’re there. This visit was no exception.

Thankfully, the traffic going out was not too bad. If you are planning on visiting the Hamptons, or anywhere else on the East End this time of year, be warned that the traffic can be backed up for miles depending on the day and time of your visit. The road leading into Sag Harbor is quite beautiful, overlooking water on both sides. I was able to stop at the beach along the way and admire the clouds and blue sky before continuing on to the main part of town. It was a cool and windy day that felt more like late September.



The first stop upon arrival was at the Port of Sag Harbor information center where a knowledgable woman, and 20-year resident, pointed out all of the things to do and see in the town. She was enthusiastic and I enjoyed talking to her and learning more about the town and her life there. Her best advice for tourists was to just “get lost” and explore the many side streets off the beaten path. Lastly, she offered a few suggestions of where to go for lunch. I noticed some restaurants along the main drag in town, but they were pricey and seemed ordinary. One place she suggested in particular sounded good to me – The Dockside Bar and Grill on Bay Street. As the name implies, the restaurant is right across the street from the docks and offers indoor and outdoor seating. She raved about the seafood, which was just what I was in the mood for.


The stroll over to The Dockside was very pleasant. A scenic street leads the way to the restaurant and is overlooked by a marina. As someone who has seen my fair share of yachts, even I was impressed with what was docked in this marina! The restaurant was bustling and people were waiting outside when I put my name on the list to be seated. They said it would be about 20 minutes for a table inside to open up. The 20 became 40 minutes, but I used the time to answer some work emails and watch the boats. Once inside, I noticed the restaurant had the beach vibe you would expect of a coastal place – a lot of white, blue and marine decor. It was open and airy with a nice view of the water.


The menu made for some tough decisions. Calamari? Clams? Seafood Paella? Too many choices. I ordered a pink sangria, hoping that it would help me narrow down my options. The cool sangria coupled with a cucumber garnish was refreshing after a morning of walking in town. A final perusing of the menu resulted in a new find – breaded scallops with French fries. I had never had breaded scallops, but thought it sounded interesting.



After a short wait my lunch arrived, looking every bit as delicious as I had anticipated. The five scallops were large and tender and the bread crumbs added just the right amount of seasoning and texture. Overall, the dish was uniquely prepared and I would order it again. The restaurant was incredibly charming and worth the wait to be seated. I felt relaxed after lunch and ready for more exploring.


The best part of Sag Harbor is the laid back feeling the town offers. While wandering I found a few houses I wouldn’t mind living in, and some historic properties undergoing renovations. On the walk back to the car there was an old church under construction. I couldn’t help but stare at its majestic beauty. So much so that the foreman actually came over to show me some old wood where bees made a hive and honey. He explained that he and his crew were working on a two-year project to turn the old church into a residence. I can’t wait to see the house when it is completed, as he said it will have three levels!


My day in Sag Harbor was just what I needed to escape and feel rested. If you are looking for a short day trip I would highly suggest this town. It’s a quick jaunt to the Hamptons if you are interested in shopping or if you are heading to Montauk. Aside from the traffic, parking can be a little dicey, but there are plenty of side-streets if you are willing to be slightly farther from Main Street. I am thankful for the helpful advice offered by the woman at the information center. Sag Harbor has a lot to offer visitors, and plenty of history for those inclined to take tours.



  1. My boyfriend and I have been trying to plan a weekend getaway for a while now, but we haven’t been able to decide where to go. I think Sag Harbor is high on our list now after seeing these incredible pictures. Seems like you had an amazing time!

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