Classic surfing-town hipness. Where the Hamptons end, Montauk Begins
Montauk, on the easternmost tip of the South Fork, is one of the sports fishing and surfing capitals of the world, as well as home to the oldest lighthouse in Long Island. Take Montauk Highway East and go to the very end, where you will run straight into the lighthouse. The Montauk Historical Society maintains the lighthouse, keeper’s dwelling, outbuildings and grounds, while the US Coast Guard operates it -- there’s a nice museum in the keeper’s dwelling. Visitors are welcome to climb the 137 spiral steps to the top of the lighthouse and, on a clear day, look out at Block Island across the sound.
A visit to Montauk Harbor is a must when you are out here. Stroll through while watching the fishing boats go in and out of the harbor. Sample a true fisherman’s hangout at the Westlake Marina’s Chowder House – the fishing boats pull up right off the deck of the restaurant.
In early spring, don’t miss the Montauk St. Patrick’s Day parade. Usually held the Sunday after St. Patrick’s Day, it is the second largest parade in our area, after the New York City parade.
If you happen to be in Montauk in early June be sure to catch the Blessing of the Fleet, which kicks off the summer season and combines a festive atmosphere with a somber reminder of those lost at sea the previous season.
Also one of the best surfing destinations on the entire US east coast, Montauk is known for its quality waves and consistency of swells. There are many different spots to choose from according to your level, the tide, swell direction, or wind conditions. Stop by one of the 4 local surf shops to get all the necessary info and gear.
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Wineries / Vineyards
If mountain biking or hiking is your thing, Montauk’s defiant single-track trails take you through some of the most beautiful natural preserves you can imagine. Montauk’s local bike shop can direct you to all the best trails and outfit all your equipment needs.
Kayaking and stand-up paddle-boarding are also hot topics here in Montauk, with plenty of challenging paddles for all levels. Contact Air & Speed for all your kayaking and paddle-boarding needs.
If it’s golf that you’re after, be sure to play the championship course at Montauk Downs State Park, one of the world’s best - and public - courses.
For all you endurance athletes, the Montauk Triathlon is a yearly event that draws many top athletes from around the country. Road biking and running junkies also head to “The End” in numbers for their share of the superb roads and many demanding loops surrounded by astonishing landscapes.
Do you fancy equestrianism? Then horseback ride on the beach at Deep Hollow Ranch, the oldest continually operating cattle ranch in the United States, or Rita’s Stables, both featuring petting zoos for kids.
All oenophiles (but you don’t have to be!) will be enthralled by Long Island’s wineries, which seriously merit a tasting tour. Only rivaled by California’s wine country, Long Island’s wine industry has grown from one small vineyard to nearly 3,000 acres of vines and over two dozen wineries producing world-class wines. The praise and awards continue to accumulate, and Long Island wines just keep getting better.
The sole staff can assist in arranging any special activity. Please inquire if you need assistance.