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  • Writer's pictureALEXANDRA


Like I said in my last post, we went to Greenport, New York for a week to celebrate my mom's birthday! We ended up staying at the cutest hotel called Sound View, with breathtaking views the water. When we weren't relaxing on the beach, we were exploring the town of Greenport and all it has to offer. Here is my guide of must-eat-at restaurants! STAY TUNED for more of my guide to Greenport, New York to hear all about the activities we did!

208 Main Street, Greenport, NY 11944

Bruce & Son is a cute little brunch spot on the main stretch of Greenport. Unfortunately, we didn't get to try out the food but the menu looks absolutely amazing and the front porch looks like a great place for people watching, especially in the busy season of summer! If you like avocado toast or eggs benedict I would head here!

111 Main Street, Greenport, NY 11944

We just happened to walk up to Claudio's Waterfront on the first day of our trip as we explored the town. I am SO GLAD we did because the food was delicious and the ambiance was A+! We ordered the chicken wings and bang bang shrimp for appetizers and I had the lobster mac & cheese for dinner. SO GOOD! Claudio's is a great place to watch the sunset as well so if you're not in the mood for food definitely head here for some cocktails!

37 Front Street, Greenport, NY 11944

Little Creek Oyster Farm & Market is a super laid back restaurant where you can even shuck your own oysters! Plus, they have apparel and glassware emblazoned with the phrase "SHUCK YOUR SELF," which make for perfect for souvenirs!

119 Main Street, Greenport, NY 11944

From the second we said we were going to Greenport, everyone said we must go to Lucharito's - and they were right! The restaurant is decked out in bright decor, making it super fun, and their menu is AWESOME! I had the pulled pork taco and the bang bang shrimp taco which were both incredible. I also really loved their homemade salsa, guacamole and queso!

300 Main Street, Greenport, NY 11944

I can only imagine how poppin this place is in the heart of summer! The vibe at American Beech is so eclectic and the decor is gorgeous. I could've spent the whole night there, and would highly recommend heading here if you are with a group of friends. There is a cute outdoor bar, an open air dining area with a fire pit, and a cozy and intimate dining area inside the restaurant. For dinner I had the tuna with crispy brussels sprouts and it was absolutely delicious!

I can't wait to get back to Greenport and try out some of the other amazing restaurants that were recommended to us. If you have any restaurants that YOU love, please leave them in the comments!

xoxo. Alexandra



Hey guys! My name is

Alexandra Dempsey, I am 31 years old and live in Stowe, Vermont.

I recently decided to start this blog to give you all a look into the life of a tour wife - the highs, the lows, and EVERYTHING in between!

My rock star husband, Ryan Dempsey

of Twiddle, stands by me every step

of the way as we journey on this whirlwind we like to call the "tour life."

Follow along on my travels, hear

stories from fellow tour wives, and

earn about some of my favorite things. Hope you enjoy and

thanks so much for reading!!

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