Travelogue – Offseason Overnight in Sag Harbor, NY

After 8 years (8 years?!?!) in NYC, I’ve been lucky to explore much of the east end of Long Island.  I realized late this fall that this past summer was my first summer with no trip out East and I missed it!  My mom came to visit so I used that as a perfect excuse to pop out for a quick 24 hour trip to hit all of my favorite places.  
So unlike me, but I left this trip up to spontaneity, we knew we wanted to escape the city for a night but didn’t have a set plan or agenda.  I woke up on Sunday morning and started calling places for availability.  It happened to be Columbus Weekend and was the Film Festival in East Hampton so prices weren’t as much of a bargain as I was hoping for in the off season.  We found the last room at The American Hotel in Sag Harbor, a reasonable deal at $200 for the night.  I had also considered Baron’s Cove and the Sag Harbor Inn but I’m so glad fate would have us at The American Hotel, it was much more central in town and had a charming, old-world feel.  The restaurant also came in handy as we were there in the midst of hurricane Matthew and we were able to practically wear our slippers downstairs to the dining room for a lovely dinner.       
We rented a car and made the drive out east.  I drove us straight to The Lobster Roll, I needed my fix of a perfect lobster roll and sweet potato fries!!  This restaurant is now prominently featured in the show The Affair, and they’ve certainly exploited their newfound fame, with show paraphernalia all over the restaurant!  My mom’s heard me talk about this place for years so was fun to finally show her.  We split one hot and one cold lobster roll and those perfect fries!  

After lunch, we explored the shops in Amagansett, East Hampton, and finally made our way back to Sag Harbor.  After a day of rain that would.not.stop. we were thrilled to see our cozy attic room.  While the hotel is certainly old, the bed was extremely comfortable and the bathroom was nicely updated.  The stairs to the attic were quirky but fun.   

I was considering dinner at The Beacon or Dopo La Spiaggia but due to the rain we decided to take advantage of the restaurant downstairs.  I’d been for lunch before but never for dinner.  It was charmingly old-school (from service to the food).  They have an incredibly extensive winelist.  We enjoyed a lovely Chablis alongside our shared entrees of scallops with truffled risotto and blackfish with lobster in a tomato vinaigrette.  

Dessert was not to be missed!  Bananas foster for 2!

The next morning we woke up to clear sunny skies and took a walk around the village of Sag Harbor.  We ended with a stop at Grindstone Donuts, I’m a shameless fan of Michael Symon and when I heard his son opened this coffee and doughnut shop I knew I had to visit.  As luck would have it, the very minute that I was in line he was there with his wife and parents!  I was too shy to ask for a picture, but I’ve now seen in person 3/5 hosts of The Chew! (Nerd alert).  

We tried the lemon poppyseed and cinnamon sugar doughnut holes!
We returned to the hotel for breakfast in the atrium.  The continental options were minimal but sufficient alongside our doughnut haul 🙂

We spent the day strolling through Sag Harbor, which in my opinion has the best selection of reasonably priced shops both old and new.  
We had one last lobster roll lunch overlooking the water at The Dock House followed by a final scoop of my favorite ice cream at Big Olaf’s (their cookie dough topper is unreal). 

All in all a successful overnight getaway from the city.  Word of warning, while many places in the Hamptons are open year-round, some were starting to close for the winter season so if you plan to head out double check opening dates and times!

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