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The best scenic stops along Montauk Highway

Take a stop along your drive

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Driving the entire length of the Hamptons along Montauk Highway probably isn’t something people would go out of their way to do, considering traffic can get serious and a single-lane highway isn’t exactly the most efficient drive. But if you find yourself along Montauk Highway for longer than expected, there are some really beautiful scenic spots along the way that often go unnoticed.

Next time you’re driving out to Montauk Point for a Sunday morning lighthouse trip, or next time you’re on your way back west to the city, take your time to check out these beautiful spots.

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1. Shinnecock Canal, Hampton Bays

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Shinnecock Canal
Hampton Bays, NY 11946

Starting at the point where most people agree the Hamptons begin, the Shinnecock Canal is a great place to look out to the water. There are usually boats docked in the canal, and restaurants along the waterside are typically lit up at night.

2. Shinnecock Bay Overlook, Hampton Bays

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295 E Montauk Hwy
Hampton Bays, NY 11946

If you’re driving along County Road 80 to get to Montauk Highway, there’s a great stretch of land that looks out over Shinnecock Bay. The view is particularly great from Edgewater Restaurant.

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3. Southampton Windmill, Southampton

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39 Tuckahoe Rd
Southampton, NY 11968
(631) 632-5119
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This windmill, found on Stony Brook University’s Southampton campus, is reportedly haunted by Beatrice Clafin. The building served as her playhouse and when she was still young she fell down the steps, broke her neck, and died. There are reports of people seeing the face of a little girl looking out the windows.

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4. Hill Street, Southampton

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Hill St
Southampton, NY 11968

Even though the speed limit is a slow and “strictly enforced” 25 miles per hour along Hill Street, the course of the road is beautiful.

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5. Agawam Park, Southampton

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23 Main St
Southampton, NY 11968
(631) 283-0247
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If you have time to stop, Agawam Park is a great place to break from a drive to eat lunch and feed some ducks.

6. Parrish Art Museum, Water Mill

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279 Montauk Hwy
Water Mill, NY 11976
(631) 283-2118
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The Parrish Art Museum has beautiful grounds. It’s a fun thing to catch on your drive past.

7. Corwith Windmill, Water Mill

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Montauk Hwy
Water Mill, NY

Located on Montauk Highway in Water Mill, the Corwith Windmill stands on a site that used to be home to another windmill—but the first windmill was actually destroyed in a three-day blizzard in 1811.

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8. Hayground Cove, Water Mill

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Hayground Cove
Water Mill, NY 11976

Hayground Cove is another beautiful scenic stop for those who need the sound of running water.

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9. Poxabogue Pond, Sagaponack

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Poxabogue Pond
Sagaponack, NY 11937

Not only is there Poxabogue Pond, but there’s Little Poxabogue Pond, and an adjacent Poxabogue County Park. Plenty of nature scenes.

Long Pond Green Belt

10. Sagg Swamp Nature Preserve, Sagaponack

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Sagg Rd
Sagaponack, NY 11962
(631) 329-3981
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Sagg Swamp is a local favorite.

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11. Wolffer Estate Vineyards, Sagaponack

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139 Sagg Rd
Sagaponack, NY 11962
(631) 537-5106
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The stretch of land that the vineyards is set on is beautiful to drive past.

12. Town Pond, East Hampton

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Town Pond
East Hampton, NY 11937

Right near the South End Cemetery, Town Pond may be small, but it’s worth a stop.

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13. South End Cemetery, East Hampton

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34 James Ln
East Hampton, NY 11937
(631) 324-0362

It may seem weird to have a cemetery listed as a scenic stop on our list, but it has some incredibly old tombstones that have been kept in great condition. Directly next to our previous map point, Town Pond, you can get two birds with one stop stopping in this East Hampton village spot.

14. Maidstone Club, East Hampton

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29 Maidstone Ln
East Hampton, NY 11937
(631) 324-0510
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The historic Maidstone Club is set on some of the most beautiful land in the Hamptons—which is part of why it has such a good reputation.

15. Napeague State Park, Napeague

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Napeague State Park
Napeague, NY

Pretty much all of Napeague consists of Napeague State Park, so it’d be a shame to not take a stop to view the beautiful land.

16. Hither Hills State Park, Montauk

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164 Old Montauk Hwy
Montauk, NY 11954
(631) 668-2554
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Driving to and from Montauk is so beautiful largely because of the state parks that you drive through getting there, Hither Hills being the main one.

17. Hither Woods Preserve, Montauk

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Montauk Point State Parkway
Montauk, NY 11954

Hither Woods Preserve is an extension of Hither Hills State Park, and the wooded area is just so peaceful to drive past.

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18. Fort Pond, Montauk

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Fort Pond
Montauk, NY 11954

If you’re really feeling like you need a break from driving, there are restaurants on and near Fort Pond that you can enjoy the view from.

19. Montauk Downs, Montauk

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50 S Fairview Ave
Montauk, NY 11954
(631) 668-5000
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This golf club is a great place to stop for a view of peaceful golfing.

20. Shadmoor State Park, Montauk

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Shadmoor State Park
Montauk, NY 11954

Shadmoor State Park is right on the water. Stop by the beach and snap a few photos.

21. Lake Montauk, Montauk

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Lake Montauk
Montauk, NY 11954

Drive along West Lake Drive or East Lake Drive to soak in those views.

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22. Oyster Pond, Montauk

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Oyster Pond
Montauk, NY 11954

Located right off the bay, Oyster Pond has amazing water views of the pond and bay alike.

Google Maps

23. Camp Hero State Park, Montauk

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Camp Hero State Park
Montauk, NY 11954

The park that Stranger Things was based on is definitely a bit creepy at times, but well worth the stop.

24. Montauk Point Lighthouse, Montauk

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2000 NY-27
Montauk, NY 11954
(631) 668-2544
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A tourist and local favorite alike, the Montauk Point Lighthouse is a great place to end your scenic drive out to the easternmost point on Long Island.

1. Shinnecock Canal, Hampton Bays

Shinnecock Canal, Hampton Bays, NY 11946

Starting at the point where most people agree the Hamptons begin, the Shinnecock Canal is a great place to look out to the water. There are usually boats docked in the canal, and restaurants along the waterside are typically lit up at night.

Shinnecock Canal
Hampton Bays, NY 11946

2. Shinnecock Bay Overlook, Hampton Bays

295 E Montauk Hwy, Hampton Bays, NY 11946

If you’re driving along County Road 80 to get to Montauk Highway, there’s a great stretch of land that looks out over Shinnecock Bay. The view is particularly great from Edgewater Restaurant.

295 E Montauk Hwy
Hampton Bays, NY 11946

3. Southampton Windmill, Southampton

39 Tuckahoe Rd, Southampton, NY 11968

This windmill, found on Stony Brook University’s Southampton campus, is reportedly haunted by Beatrice Clafin. The building served as her playhouse and when she was still young she fell down the steps, broke her neck, and died. There are reports of people seeing the face of a little girl looking out the windows.

39 Tuckahoe Rd
Southampton, NY 11968

4. Hill Street, Southampton

Hill St, Southampton, NY 11968
Google Maps

Even though the speed limit is a slow and “strictly enforced” 25 miles per hour along Hill Street, the course of the road is beautiful.

Hill St
Southampton, NY 11968

5. Agawam Park, Southampton

23 Main St, Southampton, NY 11968

If you have time to stop, Agawam Park is a great place to break from a drive to eat lunch and feed some ducks.

23 Main St
Southampton, NY 11968

6. Parrish Art Museum, Water Mill

279 Montauk Hwy, Water Mill, NY 11976

The Parrish Art Museum has beautiful grounds. It’s a fun thing to catch on your drive past.

279 Montauk Hwy
Water Mill, NY 11976

7. Corwith Windmill, Water Mill

Montauk Hwy, Water Mill, NY

Located on Montauk Highway in Water Mill, the Corwith Windmill stands on a site that used to be home to another windmill—but the first windmill was actually destroyed in a three-day blizzard in 1811.

Montauk Hwy
Water Mill, NY

8. Hayground Cove, Water Mill

Hayground Cove, Water Mill, NY 11976

Hayground Cove is another beautiful scenic stop for those who need the sound of running water.

Hayground Cove
Water Mill, NY 11976

9. Poxabogue Pond, Sagaponack

Poxabogue Pond, Sagaponack, NY 11937
Long Pond Green Belt

Not only is there Poxabogue Pond, but there’s Little Poxabogue Pond, and an adjacent Poxabogue County Park. Plenty of nature scenes.

Poxabogue Pond
Sagaponack, NY 11937

10. Sagg Swamp Nature Preserve, Sagaponack

Sagg Rd, Sagaponack, NY 11962

Sagg Swamp is a local favorite.

Sagg Rd
Sagaponack, NY 11962

11. Wolffer Estate Vineyards, Sagaponack

139 Sagg Rd, Sagaponack, NY 11962

The stretch of land that the vineyards is set on is beautiful to drive past.

139 Sagg Rd
Sagaponack, NY 11962

12. Town Pond, East Hampton

Town Pond, East Hampton, NY 11937

Right near the South End Cemetery, Town Pond may be small, but it’s worth a stop.

Town Pond
East Hampton, NY 11937

13. South End Cemetery, East Hampton

34 James Ln, East Hampton, NY 11937

It may seem weird to have a cemetery listed as a scenic stop on our list, but it has some incredibly old tombstones that have been kept in great condition. Directly next to our previous map point, Town Pond, you can get two birds with one stop stopping in this East Hampton village spot.

34 James Ln
East Hampton, NY 11937

14. Maidstone Club, East Hampton

29 Maidstone Ln, East Hampton, NY 11937

The historic Maidstone Club is set on some of the most beautiful land in the Hamptons—which is part of why it has such a good reputation.

29 Maidstone Ln
East Hampton, NY 11937

15. Napeague State Park, Napeague

Napeague State Park, Napeague, NY

Pretty much all of Napeague consists of Napeague State Park, so it’d be a shame to not take a stop to view the beautiful land.

Napeague State Park
Napeague, NY

16. Hither Hills State Park, Montauk

164 Old Montauk Hwy, Montauk, NY 11954

Driving to and from Montauk is so beautiful largely because of the state parks that you drive through getting there, Hither Hills being the main one.

164 Old Montauk Hwy
Montauk, NY 11954

17. Hither Woods Preserve, Montauk

Montauk Point State Parkway, Montauk, NY 11954

Hither Woods Preserve is an extension of Hither Hills State Park, and the wooded area is just so peaceful to drive past.

Montauk Point State Parkway
Montauk, NY 11954

18. Fort Pond, Montauk

Fort Pond, Montauk, NY 11954

If you’re really feeling like you need a break from driving, there are restaurants on and near Fort Pond that you can enjoy the view from.

Fort Pond
Montauk, NY 11954

19. Montauk Downs, Montauk

50 S Fairview Ave, Montauk, NY 11954

This golf club is a great place to stop for a view of peaceful golfing.

50 S Fairview Ave
Montauk, NY 11954

20. Shadmoor State Park, Montauk

Shadmoor State Park, Montauk, NY 11954

Shadmoor State Park is right on the water. Stop by the beach and snap a few photos.

Shadmoor State Park
Montauk, NY 11954

21. Lake Montauk, Montauk

Lake Montauk, Montauk, NY 11954

Drive along West Lake Drive or East Lake Drive to soak in those views.

Lake Montauk
Montauk, NY 11954

22. Oyster Pond, Montauk

Oyster Pond, Montauk, NY 11954
Google Maps

Located right off the bay, Oyster Pond has amazing water views of the pond and bay alike.

Oyster Pond
Montauk, NY 11954

23. Camp Hero State Park, Montauk

Camp Hero State Park, Montauk, NY 11954

The park that Stranger Things was based on is definitely a bit creepy at times, but well worth the stop.

Camp Hero State Park
Montauk, NY 11954

24. Montauk Point Lighthouse, Montauk

2000 NY-27, Montauk, NY 11954

A tourist and local favorite alike, the Montauk Point Lighthouse is a great place to end your scenic drive out to the easternmost point on Long Island.

2000 NY-27
Montauk, NY 11954