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Lined with mom and pop stores selling odes to pollock, items made by special needs adults, homemade pesto, mustard, and jam, minimalistic home furnishings, and wineries, it’s no wonder you can spend a whole day wandering around Southold.

Southold wasn’t originally on my North Fork itinerary. I had beaches I wanted to visit and trails I wanted to hike. But when Memorial Day weekend brought about 3 days of torrential downpour, I had to adapt my plans quickly. I had to come up with innovative ways to spend 3 days out on the North Fork. During my research, I came across Main Street in Southold, Long Island. Not much was said about Southold, but I read that there were plenty of cute shops to visit. On a rainy Saturday afternoon, I decided to go checkout the scene for myself. What I found was Main Street, a street filled with unique, mom and pop shops selling everything you can and can’t imagine. It was a wonderful and whimsical way to spend the afternoon that truly brought to life the soul and community of Southold.

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