Southold was the first English settlement on Long Island in 1640, and the names of the families who arrived then are still spoken often today. The now-sizable town of Southold offers plenty of adventure, historic sites, shopping and water-related fun.
An eclectic spot bracketed by 163 miles of coastline
Southhold, like Greenport to the east, offers options, options, options — but with a more updated feel. There are a clutch of appealing wineries to visit, historic sites like the Maple Lane village, amenities like the best fresh seafood market for miles, plus marinas and a good-size business district that hugs the main highway. There are also spots where it’s easy to get away from it all.
Newer housing than most North Fork hamlets
Southfield’s year-round population of 20,000-plus has led to a nice mix of housing for everyone’s taste, with newer neighborhoods tucked in behind the farmhouses and historic buildings that typically hug Main Road. Whether you’re looking for a shingle-style manse, a sprawling country estate, a humble cabin or a brick ranch, you can find it here. Just be prepared to compete for listings. The median sale price hovers at around $735,000, and Zillow rated the 2017 market “very hot.”
Owner Charlie Manwaring has fished the local waters for over 25 years and offers the North Fork’s best retail assortment of fresh seafood. You can eat in, take out, or grab some fish, shellfish, chowder to prepare at home.
This beautifully curated Main Road interiors shop features linens, vintage hardware, locally made whitewashed tables, and glassware.
Sleep on Frette linens at this quaint inn, or book a dinner reservation for some of the best seafood anywhere. There’s also a delicious on-site food truck.