Southampton, with its stunning beaches, sweeping lawns and shingled summer “cottages,” is a high-ticket vacation spot. But with a bicycle, a Long Island Railroad ticket and a picnic in your basket, you can spend a day soaking up the pleasures of this exclusive resort town on Eastern Long Island — beaches ranked among the best in the U.S., shaded streets, a postcard-perfect Main Street — for about the cost of a mani-pedi. Annual permits or steep daily parking fees limit car access to the shore, but when you travel on your own two wheels, Southampton is your oyster.

Just follow these easy steps:

  • Grab your bike, helmet and lock, and bag your beach necessities, lunch and water bottle. Check the trip planner on the Long Island Railroad website for timetables and fares, and review the rail line’s bike policy page for restriction before you set out.
  • Leave early. The trip to Southampton takes about 3 1/2 hours. You’ll ride a Babylon-bound train from Penn Station to Jamaica Station, then transfer to the Montauk Branch. You’ll also need a bike pass, which costs $5, and is reusable for other trips.
  • This 13.5-mile Southampton route map, which you can view on your smartphone using the MapMyRide app, will guide you from the Southampton rail station, to the beachfront and village. It’s a flat and easy ride, but the roads are narrow in some places and distracted driving can be a problem in the Hamptons, so ride single-file and remain alert to motorist around you.
  • If your time is limited, and your sole objective is to lounge on the beach, rack your bike in the parking lot of Cooper’s Beach off Meadow Lane (see “P” on the map). The pavilion there has restrooms, water to fill your bottle, and take-out food service with tables and chairs on the deck.
  • Before or after your beach stop, a good option is to ride the length of Meadow Lane, a narrow peninsula projecting west. You’ll be wowed by the opulent beachfront homes on the south side of the road, where you’ll also find additional, more secluded public beach access points, and by the wetland views of Shinnecock Bay on the north side. The peninsula ends at Shinnecock Inlet, where you’ll need to turn around.
  • When it’s time to check out the Village of Southampton, follow Meadow Lane east. Where it joins with Gin Lane you’ll pass the historic St. Andrew’s Dune Church, a distinctive brick structures situated on the ocean. The map will lead you through neighborhood streets to the heart of the village at the intersection of South Main Street and Job’s Lane. Park you bicycle, and stroll the lengths of both streets, which are lined with boutiques, restaurants, cafes and other attractions before heading back to the train station.

View the slideshow below for a visual tour of the sights in store for you. And be sure to consult our Hamptons Riding Guide for more insider tips.

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  • Sunday farmer's market on the grounds of the Parrish Art Museum.

  • The ride along Agawam Lake leads to Southampton's oceanfront beaches.

  • Tree-shaded streets in Southampton's estate district.

  • A peak behind the hedges at the grass courts of the Meadow Club.

  • St. Andrew's Dune Church presides over the waterfront.

  • Colorful clothing and accessories, plus bike helmets and accessories, at C. Wonder.

  • Open-air cafes and shops line Southampton's Main Street.

  • Primrose Lane offers beachy dresses and cover-ups that won't break the bank.

  • Flea market at the Southampton Historical Society.

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