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Hamptons.com
April 7, 2024

The Evolution and Legacy of NY Route 27: From Indian Trails to Modern Highways

T.J. Clementeby T.J. Clemente
in Community, Trending
Home Community
The Evolution and Legacy of NY Route 27: From Indian Trails to Modern Highways

NY Route 27 East is the lifeline, pipeline, and only direct line to the Hamptons. It is the longest state route on Long Island, stretching 120.58 miles. It starts in Brooklyn, N.Y., and ends at the Montauk Lighthouse. Back in the 1960s, former Tonight Show host and frequent Sag Harbor visitor Johnny Carson used to jokingly call it “the world’s biggest parking lot.” Yet, to most Hampton visitors, residents, and workers, it is the road “most traveled.”

 

Old timers will tell you stories of its importance before there was a Long island Expressway. The actual signed Route 27 was born in 1920 and, at that time, only extended to Amagansett. Robert Moses, the great builder of N.Y. Highways had developed a plan to elevate Route 27 through Nassau County in order to service trucks but local store owners and businesses fought and killed the idea.

 

On the east end, it is called Montauk Highway, but like so many roads on the east end, it started out as an Indian trail. The Shinnecock Indians, as well as the Montauketts, took this route on the east end (Montauk) in order to trade wampum with other Indians located to the west. Some historians consider Adriaen Block, a Dutch Explorer, as the first known Western man to set foot in Montauk. In 1614, Block landed and interacted with the tribe at Montauk Point; Block named the Point Hoeck van de Visschers, or “Point of the Fishers.”

 

However, Lord David Lion Gardiner was the first settler to pass through Montauk while moving to Gardiner’s Island from Connecticut in 1639. As the settlement of what we now call Montauk progressed, the highway was laid out naturally as ranchers let their livestock graze on the Montauk peninsula in the 1700s. In 1792 George Washington authorized construction of the Montauk lighthouse and the project was completed in 1796. the first lighthouse in New York State. Originally Montauk Highway hugged the coast into the village and is now called Old Montauk Highway only after a more direct Route 27 was built to handle modern traffic.

 

However, over thirty years (1960-1990), the route between Lindenhurst and East Patchogue was gradually upgraded to a freeway-type road. The stretch from East Patchogue to Shinnecock Hills was built as a highway with exits from the beginning but was not updated again until the 1990s. Those with memories can remember, as did Johnny Carson, that as one approached Shinnecock Hills traveling east on NY 27, the road became three lanes only to suddenly become a single lane when it merged with County Road 39. That then formed a single lane in both directions, and that stretch was labeled “the Shinnecock Squeeze.” On weekends in the Summer, it might take over one hour to get from Hampton Bays to CR-39 with traffic stop-and-go. If a car overheated like it did back then or if there was a fender bender, then things would get uglier.

 

Using 2022 data from the National Highway Safety Traffic Administration, there were 934 highway fatalities on Long Island roads, with the majority of them (578) in Suffolk County. Although the highest number (62) deaths on Long Island occurred on Route 25, Route 27 was right behind with 62.

 

Finally, in 2006-7 more lanes were added at the “squeeze,” but anyone who was around then can remember the “cones” and massive bottlenecks that expansion created. As bad as traffic can become every workday morning and evening and on weekends like Sunday evenings heading west, nothing compares
to the pre-2006 Southampton Town Route 27 traffic jams at those same times. Oldtimers will testify that the flow has really improved, of course, to no relief to those who grapple with the traffic to get to and from work these days.

 

Trivia: The official distinction between “Montauk Highway” and Sunrise Highway is Sunrise Highway (NYS Route 27) – Connects Southampton/Brookhaven Town Line to County Road 39. Montauk Highway (NYS Route 27) – Connects North Road (County Road 39) to Southampton/East Hampton Town Line. Also, Amityville is the only town in Suffolk County where the NY 27 (Montauk Highway) is officially referred to as Merrick Road. Yet it is the same east-west road, no matter the signage and different speed limits.

 

First instituted in 1901, speed limits were assigned nationally to increase road safety. Thus, prevent accidents. Originally, individual states were responsible for determining their own speed limit laws. After oil shortages in the 1970s, Congress established a national maximum speed limit of 55 mph. The first-speed limit signs were posted at city and town limits. Early signs were not reflective. By the middle to late 20s, however, many cities required that speed limit signs be illuminated. The New York State legislature, in 1925, about the time of the official establishment of state highways, passed a law that “each city shall have placed conspicuously [signs on] each main highway, where the rate of speed changes [and signs shall be] adequately illuminated between sunset and sunrise.” That is the reason for the speed limit on Route 27 varying from 25mph in Bridgehampton by the school to 30mph traveling through Tuckahoe and 45-55mph in most other towns.

 

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May 23 @ 08:30 AM - May 24 @ 06:00 PM
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Guild Hall’s 38th Annual Academy of the Arts Achievement Awards Dinner

Guild Hall's 38th Annual Academy of the Arts Achievement Awards Dinner

  • My curiosity piqued when I saw the new, shovel-ready plans at 28 Pepperidge Lane in Amagansett. Included with this nearly two-acre property, are sophisticated and luxurious plans by the firm Resolution: 4 Architecture (RES4). New construction in the Hamptons isn’t easy—but what if your dream home could be architect-designed and delivered directly to you? What is the latest in prefab architecture in 2025?⁠
⁠
To explore this intriguing approach further, Scott connected me directly with Robert Luntz, the co-founder of RES4. See our conversation on redefining luxury through modern modular design, its growing relevance in the Hamptons, and the future of high-end prefabrication.⁠
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For more information about the plans in place at 28 Pepperidge Lane, Amagansett, contact Scott Bradley.⁠
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RES4 has been a pioneer in modern prefab architecture. What inspired you to focus on this method of construction?⁠
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We’ve spent over two decades innovating ways to deliver exceptional, modern homes efficiently and affordably. Our modular methodology uniquely allows us to combine luxury, precision, and accessibility, transforming the landscape of high-end housing by delivering refined design to a broader market.⁠
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@resolution4architecture @hamptons_waterman_lifestyle @hamptonsrealestate⁠
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Read the full interview at Hamptons.com. (Link in Bio)⁠
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#architecture #hamptons #hamptonsrealestate #luxury⁠
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  • NYC Second Chance Rescue hosted its 5th Annual Rescue Ball Gala — a dazzling evening of compassion, community, and celebration — at Pier Sixty in New York City.⁠
⁠
The event honored two inspiring individuals for their outstanding advocacy and dedication to animal welfare: Martha Stewart, iconic lifestyle entrepreneur and lifelong animal champion, and Dr. Dan Belkin, leading dermatologist and passionate rescue animal advocate.⁠
⁠
Set against the stunning waterfront views of Pier Sixty, the gala brought together philanthropists, celebrities and compassionate supporters to champion NYC Second Chance Rescue’s mission. The night featured a special live performance by Rob Thomas, a special appearance by Georgina Bloomberg, a lively auction led by celebrity host Elvis Duran, host of Elvis Duran and the Morning Show on Z100, surprise guest Alexandra Daddario, and a high-energy DJ set by GEO ROC that kept guests dancing for a cause.⁠
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📸: Sylvain Gaboury/PMC⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#secondchancerescue #nyc #marthastewart #robthomas ⁠
  • The 14th Annual Montauk Music Festival is back! ⁠
⁠
Check out the top Hamptons events this weekend!⁠
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🎶 Montauk Music Festival⁠
📅 Fri, May 16 – Sun, May 18⁠
📍 Multiple venues, Montauk, NY⁠
A volunteer-run, grassroots celebration of Montauk’s vibrant live music scene.⁠
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🐾 ARF’s Pet Celebration Day⁠
📅 Sat, May 17 | 📍 124 Daniel Hole Rd, East Hampton⁠
A tail-wagging good time! ⁠
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🧵 Airing of the Quilts⁠
📅 Sat, May 17 | 12–5PM⁠
📍 The Art Center at Duck Creek, East Hampton⁠
A beloved outdoor tradition! Bring a quilt, share your story, and explore the beauty of the log cabin pattern.⁠
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🌴 Jimmy Buffett Day at Clubhouse Hamptons⁠
📅 Sat, May 17 | 1–5PM⁠
📍 174 Daniels Hole Rd, East Hampton⁠
Tropical attire encouraged! Live music, raffles, and good vibes—all for a great cause.⁠
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🎉 Hampton Library’s Family Fest Fundraiser⁠
📅 Sat, May 17 | 2–5PM⁠
📍 Channing Daughters Winery, Bridgehampton⁠
Games, music, food trucks, and “The Sled” mobile tech library—family fun with a local flair!⁠
⁠
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🎸 Jackie Greene at The Stephen Talkhouse⁠
📅 Fri, May 16 | 7PM⁠
📍 161 Main St, Amagansett⁠
Roots rocker Jackie Greene takes the stage. Don’t miss this intimate performance!⁠
⁠
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🚲 Springs Bike Ride⁠
📅 Sat, May 17 | 10AM–12PM⁠
📍 Start: Bridge Lane over Sag Pond⁠
Ride through historic Springs after a quick tour of the local library and historical society.⁠
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😂 Comedy in The Hamptons: Joe DeVito⁠
📅 Sat, May 17 | 7–10:30PM⁠
📍 Canoe Place Inn, Hampton Bays⁠
Catch NYC comedy favorite Joe DeVito for a night of nonstop laughs.⁠
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💿 Hamptons Vinyl Record Fair⁠
📅 Sun, May 18 | 12–6PM⁠
📍 LTV Studios, Wainscott⁠
Dig through crates, catch live sets, and vibe with fellow music lovers.⁠
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🎬 Now Playing at Sunset Theater: Sinners⁠
📅 Fri, May 16 – Mon, May 19⁠
📍 2 Brook Rd, Westhampton Beach⁠
A chilling new horror film starring Michael B. Jordan and Hailee Steinfeld.⁠
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📷 Anthony Lombardo Photography Exhibition⁠
📅 Sat, May 17 | 12–4PM⁠
📍 Southampton Cultural Center⁠
A showcase of stunning visuals from a standout local photographer.⁠
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📲 Head to Hamptons.com for more events!⁠
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#hamptonsweekend #montaukmusicfestival #weekend⁠
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  • On Tuesday, April 29th, Kenneth Cole and co-hosts led a special launch event at the Core Club in New York City in partnership with the Mental Health Coalition ahead of Mental Health Awareness Month.⁠
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The evening began with an intimate reception, allowing guests to mingle and connect over cocktails. It was followed by an elegant seated dinner and a special performance from multi-platinum recording artist Rachel Platten.⁠
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Check out the full gallery at Hamptons.com (Link In Bio)⁠
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📸: Photography Courtesy of BFA: Yvonne Tnt⁠
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#kennethcole #rachelplatten #rachelrosnahan #nyc
  • It’s Mother’s Day Weekend! ⁠
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From fine jewelry to live music, art, brunches & nature — here’s what’s happening:⁠
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💎 Jen Proudman Jewelry Pop-Up⁠
🗓️ Friday, May 9 | 2–5PM⁠
📍 Le Closet, 9 Windmill Lane, Southampton⁠
✨ Shop stunning gem-carved fine jewelry while browsing luxury consignment.⁠
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🎬 Gary Cooper Festival⁠
🗓️ Fri, May 9 – Sun, May 11⁠
📍 Southampton Playhouse, 43 Hill St⁠
🌟 A weekend honoring a Hollywood icon with screenings and celebrations.⁠
⁠
🖼️ 17 Women Art Exhibition⁠
🗓️ Sat, May 10 – Sun, May 11 | 11AM–4PM⁠
📍 Ashawagh Hall, East Hampton⁠
🎨 Featuring painting, sculpture & photography by 17 female artists.⁠
⁠
🏛️ Southampton History Museum Spring Fair⁠
🗓️ Saturday, May 10 | 11AM–4PM⁠
📍 17 Meeting House Lane, Southampton⁠
🎶 Live 19th-century music, local legends, crafts, games & more!⁠
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🍳 Artists’ Table Brunch @ Watermill Center⁠
🗓️ Saturday, May 10 | 12–2PM⁠
📍 Watermill Center⁠
🥗 Chef-made meal & artist presentations in an intimate setting.⁠
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🌹 LongHouse Talks: Roses in the Garden⁠
🗓️ Saturday, May 10 | 2–4PM⁠
📍 LongHouse Reserve, East Hampton⁠
📚 Photographer Ngoc Minh Ngo shares stories & images from her new book.⁠
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🎸 The Barnstorm Live @ The Clubhouse⁠
🗓️ Saturday, May 10 | 9PM⁠
📍 174 Daniels Hole Rd, East Hampton⁠
🎤 NYC’s favorite party rock band hits the Hamptons!⁠
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🗿 Vadis Turner’s “Venus Rising”⁠
🗓️ Saturday, May 10 | 4–5PM⁠
📍 LongHouse Reserve⁠
🔥 Bold new outdoor sculpture debut + Artist Walk & Talk.⁠
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🌊 Paddle Diva’s Mother’s Day Paddle & Brunch⁠
🗓️ Sunday, May 11 | 11AM⁠
📍 Vandevere Marina, East Hampton⁠
🛶 Paddle, then brunch with Fresno. Get a free MOM-osa!⁠
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🍽️ Mother’s Day Dining Guide⁠
🗓️ Sunday, May 11⁠
🎁 Treat mom to a perfect brunch, lunch or dinner.⁠
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🎨 ArtSea Create & Sip: Horseshoe Crab Molt⁠
🗓️ Tuesday, May 13 | 6–8PM⁠
📍 Tiana Bayside, Hampton Bays⁠
🖌️ Paint + sip night celebrating horseshoe crabs. No experience needed!⁠
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📍 Check out more events at Hamptons.com (Link in Bio)⁠
#hamptonsevents #eastendhappenings #mothersdayweekend #artinthehamptons #livemusic #southamptonny #easthampton #hamptonslife⁠
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  • 7 Ashwood Court, Southampton, NY 11968⁠
Saunders Exclusive: $6,200,000⁠
@vinceinthehamptons⁠
@hamptonsrealestate⁠
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This magnificent new construction offers a blend of modern luxury and timeless sophistication. Spanning 7,546 +/- sq. ft. on a pristine 0.92-acre lot, this two-story traditional-style residence boasts 7 bedrooms, 7 full baths, and 1 half bath.⁠
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Inside, find an open kitchen adorned with marble countertops and high-end stainless steel appliances, perfect for the culinary enthusiast. The home features a spacious entry foyer, a living room, dining room, family room, den/office, and a study. Enjoy the comfort of two primary bedrooms, each with its own freestanding soaking tub, located on the first and second floors, respectively.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#saunders #hamptons #hamptonsrealestate #luxuryrealestate #southampton
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