Lost Theme Parks: 10-year Tenure of “Pleasure Island” – Wakefield, Massachusetts

in Entertainment, Theme Parks

Retro-themed artwork featuring the iconic Pleasure Island ferris wheel and classic amusement rides, with the title: “Lost Theme Parks: Pleasure Island.” This tribute celebrates the cherished Wakefield, Massachusetts destination that brought joy to generations of thrill-seekers and park fans.

Ironically billed as the Disneyland of the Northeast as Disney had its own version of Pleasure Island from 1989-2008, this Massachusetts amusement park (1959-1969) featured 48 rides before it closed.

The popular New England park has several similarities to Disneyland, California, in that it was designed by the same man who helped design Walt’s California park, Cornelius Vanderbilt Wood.  Pleasure Island also enjoyed numerous ride sponsorships in the same manner as Disneyland.

The Massachusetts amusement park was started by “Child Life” magazine publisher William Hawkes in 1959 only a few years after Disneyland opened.  Pleasure Island spanned 80 acres. Attractions at the park included a small scale railroad, petting zoo, miniature golf, and Monkey Island, which showcased the antics of the small primates.

Monkey Island’s picturesque pond features playful ducks, inviting benches, and colorful umbrellas, with a nostalgic sign proclaiming: “Monkey Island—you’ll have more fun than a barrel of monkeys.” A delightful homage to beloved lost attractions like Pleasure Island in Wakefield, MA.
Listed below are a few of the more popular rides.

Moby Dick Hunt

Adventurers would board a guided boat (guided by a driver – no tracks on this ride) and encounter sharks, a charging rhino and cannibals.  The highlight was an encounter with a  giant white whale surfacing near the boat.

A whimsical whale emerges from a river bordered by lush trees, sending a playful spray skyward—capturing the magical nostalgia of classic Pleasure Island in Wakefield, Massachusetts, once a beloved Lost Theme Park attraction.

Ride the Old Chisholm Trail

After boarding a carriage, travelers were taken back in time to the old west.  Along the way they would encounter angry cattle; a hanging at the town jail, and a final run in with a gunslinger inside the piano bar.

Cowboys duel in front of the iconic “Chisholm Trail” sign, thrilling guests gathered at Pleasure Island in Wakefield, Massachusetts—a classic moment from one of New England’s beloved lost theme parks.

Pirate Boat Ride

Pirates were the theme of the free floating boat ferrying passengers to Captain Kidd’s Treasure Island.  Along the journey the boat’s skipper spieled with bad puns and jokes until reaching the destination.  Cannon fire greeted the party as they approached the landing.

A nostalgic riverboat packed with guests glides smoothly past the dock and the iconic “HATE COVE” sign at Pleasure Island in Wakefield, Massachusetts—once a must-visit destination among legendary theme parks and fondly remembered by amusement park fans.

Space Rocket

The centerpiece of this attraction was an Atlas Mercury rocket. The Mercury program was the forerunner to the Apollo moon landing program. Riders were strapped into position and then experienced the sensation of lift off, via centrifugal force, while viewing images from “space” seen at the top of the capsule.

Vintage Pleasure Island poster featuring a rocket ship soaring near a glowing yellow moon, promoting the thrilling Space Ride attraction at Wakefield’s legendary, long-lost amusement park.

Wreck of the Hesperus

Based on the poem by Henry Wadsworth Longfellow, this dark ride took guests aboard a small sailing ship shaped ride vehicle for a maritime adventure that culminated in an encounter with King Neptune.  After “sinking” as the result of a terrible storm, riders enjoyed an “underwater” view of the ocean complete with giant animated sea turtle and circling shark.  Neptune chided, “Beware ye who have desecrated my kingdom!” as the boat made its exit.

Visitors gather around the iconic Wreck of the Hesperus shipwreck attraction at Pleasure Island in Wakefield, Massachusetts, with nearby park buildings, leafy trees, and a flagpole adding to the nostalgic atmosphere of this legendary New England theme park.

 

Pleasure Island also featured headline entertainment from stars like Cesar Romero, the Three Stooges, Michael Landon, Jerry Mathers (the Beaver) and Clayton Moore (the Long Ranger).  Gunfights would break out regularly in the Western area of the park.

The most popular entertainment venue in the park was the Diamond Lil Saloon which featured performances by Diamond Lil (based on the Mae West character, not the Marvel comic).  Sponsored by Pepsi, this late 1800’s saloon offered four shows daily, with an additional show each day on the weekend.  The show was produced by former Disneyland public relations and show promotion executive Lloyd Settle.

Performers light up the stage as an enthusiastic audience revels in the ornate, vintage theater at Pleasure Island, Wakefield’s beloved entertainment haven—capturing the grandeur and excitement that once made this iconic theme park a regional favorite.

Due to the short summer seasons of New England the amusement park only operated for ten years, closing in 1969.  Edgewater Office park now occupies the area which once called this historic park home.

Sources: Friends of Pleasure Island, Wikipedia
Images: NOBLE web, Friends of Pleasure Island

in Entertainment, Theme Parks

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