The Paul McCartney: Amagansett Bike Ride or Drive

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Sights: This ride takes you to Paul McCartney’s house, the mansions of Devon Colony, the funky Fish Farm, Napeague State Park, some lovely bay beaches, the Devon Yacht Club, and to Lazy Point, the most popular wind- and kite-surfing location in the Hamptons.

Distance: 11.8 miles.

Starting point: The Amagansett train station. Bikes are allowed on the Long Island Railroad as long as you are not traveling during rush hour, or on holidays. If you have a car, you can park in the station parking lot, or along the Route 27. After you exit the station, turn left. When you reach the railroad crossing, turn left. Ride over the tracks and then stay to your right onto Abraham’s Landing Road. At the first intersection, turn left onto Fresh Pond Road. The first house on your right will be…

Paul McCartney’s house

20 and 26 Fresh Pond Road

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Why would young Paul, at the height of his Beetle mania fame, buy a modest house in the tiny hamlet of Amagansett where not much was happening at the time?

Love.

Paul had fallen in love with Linda Eastman, a photographer from Scarsdale, NY.

Love led to marriage, which led to in-laws, which led to visiting the in-laws, who were well-off and had a summer house in East Hampton. Smitten with the Hamptons, Paul bought the modest shingle structure you see to the left of the driveway entrance, as well as the 22 acres surrounding it. He, Linda, and their children spent summers here until Linda died of breast cancer in 1998. That loss devastated McCartney who, other than the 10 days he spent in a Tokyo jail for marijuana possession, had never spent a night apart from his 56-year-old wife. 

Four years later, McCartney married Heather Mills. Local real estate agent lore has it that Mills did not want to live in the house Paul had so happily shared with Linda. Understanding how she felt, Paul purchased 11 Pintail Lane, a house with a pool on a small cul-de-sac abutting the edge of his property. That marriage ended in divorce and, when he married trucking company executive executive Nancy Shevell in 2011, his digs became noticeably fancier. Up went a brand new house on the Fresh Pond Road side of his property (bringing the total number of houses on his compound to 3), deer fencing, and a gated driveway.

Paul’s daughter, fashion designer Stella McCartney, has a place nearby in Napeague . Known as a nice guy by all who have met him here, Paul and his family can frequently be seen in town living as simple and normal a life as possible for someone of his stature. As his independently wealthy, successful wife once told The New York Observer, “I’m over 50. I work. That’s it.…There really isn’t much to talk about.”

Return to Abraham’s Landing Road and turn left. In 1 mile, turn right  on Cross Highway East.  You will be approaching…

The Devon Colony

In 1906, two millionaires from Cincinatti -- Richmond Levering (of Lever Brothers) and William Cooper Procter (of Procter & Gamble) were invited on a hunting trip to Montauk by their friend Arthur Benson, who had recently purchased most of the land there. The visitors loved the area so much that they asked Benson if they could buy some of his mostly uninhabited acreage. Having heard that the Long Island Rail Road was about to extend its tracks out to Montauk – which meant his land would soon vastly appreciate in value – Benson said no. 

But, he suggested, why didn’t the guys take a look at nearby Amagansett Highlands, whose high elevation overlooked Gardiners Bay on one side and the ocean on the other. The men, along with two other wealthy Cincinatti businessmen – Joseph Rawson Jr. and William Stanhope Rowe -- went on to buy about 2,000 acres for 50 cents an acre. Four gorgeous stucco mansions went up to house their families and servants, and Levering built a fifth house for his mother Julia. (18 Cranberry Lane) (The only one not made out of stucco)

The families made the days-long trek out here from Cincinatti every summer, beginning in 1909. They had strong social ties to each other and spent their days going to the beach, sailing, swimming, socializing with each other, and entertaining, and established what is now the Devon Yacht Club, which we will see at the end of this ride.

Levering House

30 Cross Highway East

The grounds in front of the Levering mansion

The grounds in front of the Levering mansion

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After Richmond Levering died in 1920 at the age of 39 in the Spanish Flu epidemic, his mother donated a house and land on Main Street for the town to use in his memory as the Amagansett Free Library.

Rawson House

10 Cross Highway East

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Originally called Red Roof, the name of the house was changed to Windy Dune after the 1938 hurricane blew off its red roof tiles. John Mackall, the son of the Rawson’s, has said his house — as well as the others in the colony — was always packed with people and it was “nice… to be living in a tribe, rather than a nuclear family.”

At the next corner, turn left onto Cranberry Hole Rd. On your left, you see the front of the Rawson house shown in the photo above. Remember, Cranberry Hole Rd. did not exist when the Rawsons lived here. Their view from the porch, above, was an unobstructed one of the ocean. At the next corner, turn left onto Ocean View Lane. On your left will be…

Procter House

3 Ocean View Lane.

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Of all the original mansions, the Proctor house is in the best shape, having received the most contemporary TLC.

On your right is the…

Rowe House

2 Ocean View Lane

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This is quite the imposing structure. It looks more like a boarding school more than a house.

At the side of the mansion, is the clothesline where the original owners hung their laundry.

At the side of the mansion, is the clothesline where the original owners hung their laundry.

In 0.6 miles, you will reach Cranberry Lane. On your right, you will see the house Levering built for his mother, Julia.

Julia Levering’s house, at 18 Cranberry Lane, was the only one of the original five houses that was not made of stucco. To see photos of the inside of the house, click here.

Julia Levering’s house, at 18 Cranberry Lane, was the only one of the original five houses that was not made of stucco. To see photos of the inside of the house, click here.

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We will be turning onto Cranberry Lane but, for now, cross the intersection and, in the grass on the right, look for this plaque his mother had engraved in his memory. In part, it reads, “Inscribed in the honor of Major Richmond Levering who founded the colony of Devon in 1908” and “built the Devon Yacht Club in 1911.”

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Directly across from the start of Cranberry Road, you will see these two stone markers, located at the rear entrance of Richmond Levering’s estate. This was the path he would have taken to walk to his mother’s house.

Take Cranberry Road past Julia Levering’s house until Cranberry Lane ends in a T at Cranberry Hole Road. Turn left onto Cranberry Hole Road. The road will become very beachy in feeling and, soon, you will see water on both sides. In 1.03 miles you will reach…

The Fish Farm

429 Cranberry Hole Rd.

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If you didn’t know better, you would be tempted to keep pedaling right by this place without giving it a second look. But this rather derelict driveway leads to a unique husband and wife business.

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The husband raises striped bass — both in pools and in cages offshore — for commercial use and the wife runs a funky market and cafe, shown at right in the photo.

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You can bring your food outside and eat at picnic tables overlooking the bay. For more info, click here.

Continue on Cranberry Hole Rd. In anofher 0.4 miles you will reach…

Napeague State Park

Stop and hike the 1.8 mile Promised Land Trail. This lovely hike takes you through woodlands dappled with pitch pines and cacti (rare on Long Island), past the ruins of the Smith Meal Fish Factory, and to the beach at Napeague Bay. Someone has adorned branches along the route with lovely sea shells, adding to the charm of the walk.

Follow Cranberry Hole Rd for another 0.8 miles. At the end of the pond, turn right onto Crassen Blvd. and then left onto Shore Drive East. Directly across the water from the first house on Shore Drive (number 72) you will see the Art Barge. Established by Victor D’Amico, the founding Director of the Education Department at the Museum of Modern Art, the Art Barge offers various arts classes for children and adults. You have now entered…

Lazy Point

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This is the main settlement in Napeague. The fishing shacks that still dot the area were built the late 1800s to house workers from the Smith Meal Fish Factory. People who live here own their homes, but most do not own the land their houses stand on. That land is owned by East Hampton Town Trustees who rent the land for a modest price to the owners.

Bike to the end of Shore Drive, then head back the way you came. Turn right onto Crassen Blvd, then make an immediate  left onto Shore Drive West. This very quickly brings you to a pretty water view. Make a u-turn and head back to Crassen Boulevard. Turn right and bear immediatelty right onto lazy Point Road. In 0.3 miles, you will reach a fork in the road. Go straight to…

Lazy Point Beach

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This is the place for wind- and kite-surfing the in Hamptons. If you want to give kite-surfing a try, check out the lessons given here by Sky Walk Kite Boarding.

Continue biking, or driving, through the parking area (the water will be on your right). Keep going until the road ends in a T. At the T, turn left. This will put you back onto Lazy Point Road. Turn right onto Shore Road. This pretty street will bring you back to Cranberry Hole Rd. Follow Cranberry Hole Rd. for ___ miles and turn right on Bendigo Rd. This ends in a T at Abraham’s Landing Rd. Turn right and, immediately in front of you will be…

Devon Yacht Club

This unassuming-looking, exclusive club was established by the Ohio-based millionaires of the Devon Colony. Although the buildings have been updated and renovated, they stand in their original locations.

Levering Bath House






Richmond Levering and his wife separated and, finally, divorced in 1915. A year before the divorce was finalized, he built this bath house across from the entrance to Devon Yacht Club for the Broadway star Hazel Dawn, whom he was seeing. The beach-front house had four changing rooms and a large sitting room with a fireplace. It was sold as part of the Levering estate in the 1920s. When After the purchasing family eventually sold the estate, they kept this house and turned it into a summer home.


Head back the way you came on Abrahams Landing Path until you reach Route 27. Turn right and you will soon be at our starting point for this ride, the Amagansett train station.  

Text and photos by Irene Daria



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