Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Road cycling routes
United States
New York
Suffolk County
Southampton

Sag Harbor – Water Mill Windmill loop from Southampton

Routes
Road cycling routes
United States
New York
Suffolk County
Southampton

Sag Harbor – Water Mill Windmill loop from Southampton

Easy

4.5

(4)

13

riders

Sag Harbor – Water Mill Windmill loop from Southampton

01:48

45.9km

190m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: October 15, 2025

Download GPX

Save

Move start point

Edit route

Navigate

Send to Phone

Waypoints

A

Start point

Train Station

Get Directions

1

28.9 km

Lance Corporal Jordan C. Haerter Memorial

Highlight • Bridge

The community dedicated this bridge to honor a 19-year-old native of Sag Harbor who sacrificed his life while fighting in Iraq. Following his death, he received recognition for his "extraordinary …

Tip by

2

29.1 km

Sag Harbor

Highlight • Settlement

Sag Harbor is a picturesque village on the East End of Long Island, New York. It boasts a rich maritime history dating back to the 18th and 19th centuries and …

Tip by

3

30.4 km

Otter Pond

Highlight • Lake

Otter Pond is part of the Long Pond Greenbelt, known as the "string of pearls" due to its chain of 13 rare coastal plain ponds. These fragile ecosystems are crucial …

Tip by

4

41.7 km

Water Mill Windmill

Highlight • Monument

The Water Mill Windmill at 695 Montauk Highway in Water Mill, New York, holds historical significance as a tangible link to the area's past. Erected in the 18th century, it …

Tip by

B

45.9 km

End point

Train Station

Way Types & Surfaces

Way Types

21.3 km

12.5 km

7.89 km

4.23 km

Surfaces

45.9 km

Sign up to see more specific route details

Sign up for free

Elevation

Elevation

Sign up to see more specific route details

Sign up for free

Weather

Powered by AerisWeather

Today

Monday 17 November

7°C

2°C

0 %

If you start your activity now...

Max wind speed: 27.0 km/h

to get more detailed weather forecasts along your route

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Loading

Nearby routes

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Moderate

4.0

96

Hither Hills & Montauk Point State Park via Montauk Point State Parkway loop

04:01h

101km

420m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Moderate

4.5

125

Montauk Point State Parkway – Montauk Point Lighthouse loop from East Hampton

03:22h

79.0km

340m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Moderate

5.0

63

Truman's Beach – Hashamomuck Beach loop from Mattituck

03:41h

83.8km

220m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Moderate

4.8

74

Shelter Island Heights loop from Greenport West

01:56h

40.8km

320m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Easy

4.5

46

Ponquogue Bridge View – Dune Road loop from Westhampton

01:55h

44.5km

80m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Easy

5.0

44

Truman's Beach – Orient Beach loop from Greenport

01:33h

34.8km

60m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Moderate

44

Sag Harbor – Napeague State Park loop from Sag Harbor

03:28h

88.4km

360m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Moderate

4.5

37

Dune Road – Ponquogue Bridge View loop from Westhampton

02:37h

59.5km

180m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Easy

4.0

25

Dune Road – Ponquogue Bridge View loop from Hampton Bays

01:28h

37.2km

80m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Easy

5.0

31

Napeague State Park – Napeague Harbor loop from East Hampton

01:51h

44.8km

110m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Easy

22

Sag Harbor loop from East Hampton

01:34h

38.8km

180m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Moderate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Hard
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Easy

28

Dune Road loop from Westhampton

01:27h

34.1km

40m

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepacking
B2B
PartnersConnectEmbed routes
Company
PressWhat's NewPioneersProduct UpdatesAmbassadorsAdventure Hub
Community
Help GuidesSupportKomoot Treasure Hunt
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy
Terms of Service
Community guidelines
Vulnerability disclosure program
Imprint
Information for law enforcement