A historic hamlet can be found on Long Island’s North Fork, tracing its stunning history back to 1640 when it was founded by English settlers. Southold prides itself on being one of the first English colonies in New York and played an important role in colonial America’s early days. The hamlet has been shaped by strong agricultural roots and maritime ventures.

Southold has become a sought-after vacation destination, as in addition to its rich history it boasts a long tradition of horse racing and is filled with parks, landmarks, and museums. The city is also home to stunning beaches, arguably some of the best in North Fork, creating an ideal spot for travelers to relax and enjoy a quiet getaway.

This beloved destination has blended its historical roots with a welcoming air for its residents and visitors. Below are some of the must-visit summer sites in Southold. 

  1. Founders Landing Park: There is more to this park than may meet the eye. Once known as the Southold Wharf, a hub for steamships bringing goods and services, Founders Landing Park is packed with history. In the 19th century, a dock was added to help ferry city residents to the East End, while also providing local farmers with the opportunity to transport vegetables to NYC and Connecticut. While the Long Island Rail Road eventually acquired and closed the wharf down, the Ladies Village Improvement Society bought the land in 1906, making it Southold’s first official park in 1907. Today Founders Landing Park is a family-friendly spot with a playground and picnic tables.
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  1. McCabe’s Beach & Kenney’s Beach: Southold beaches are picturesque must-visits. With McCabe’s Beach equipped with lifeguards on duty during the summer season, restrooms, and shower facilities, Southold invites you to enjoy a summer day on this 900-foot-long beach of soft sand. A short half-mile walk west will find visitors on Kenney’s Beach, another gorgeous beach operated by the town. Kenney’s Beach is perfect for a relaxing afternoon or a quiet sunset stroll.
  1. Southold Indian Museum: While many may come for the beaches, Southold is filled with history that shouldn’t be missed. The Southold Indian Museum, which is managed by the Long Island chapter of the New York State Archaeological Association, is an important trip for visitors hoping to learn about the area’s indigenous peoples. Expect to see a diverse collection of artifacts from the Native Americans who inhabited the area. The Southold Indian Museum is a must-see for those interested in local archaeology and natural history.
  1.  The Custer Institute and Observatory: Benefiting from some of the darkest skies on Long Island due to lower light pollution, the Custer Institute and Observatory is the island’s oldest public observatory. Facing Peconic Bay and Shelter Island, the observatory hosts a number of events throughout the summer that welcome visitors to explore the night sky.
  1. Horton Point Lighthouse: Constructed in 1857, Horton Point Lighthouse stands 58 feet tall and is one of eight historic lighthouses in Southold Township. Horton Point Lighthouse warns of the treacherous shoreline of the Long Island Sound. Once managed by keepers until its automation in 1993, visitors can explore the main floor of the keepers’ quarters, which was transformed into the maritime museum that highlights the lighthouse’s history.