Head Of The Harbor, a village on Long Island's north shore in New York, is characterized by its preserved natural beauty and historic charm. The area features a blend of winding country roads, diverse ecosystems including woodlands and wetlands, and scenic waterfront views of Stony Brook Harbor. This landscape provides a setting for several sports like hiking, road cycling, mountain biking, jogging, and more.
Outdoor enthusiasts exploring Head Of The Harbor will…
46
Routes
4.5
(24)
Average rating
376
People visited

5.0
(1)
3
hikers
8.73km
02:21
110m
90m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

2
hikers
2.70km
00:42
20m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

1
hikers
1.40km
00:22
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

2.15km
00:34
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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8
riders
78.6km
03:24
480m
480m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

1
riders
91.6km
04:04
710m
710m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

19
riders
47.3km
02:25
430m
430m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

4.0
(1)
26
riders
69.9km
03:09
600m
600m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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5
riders
9.73km
00:47
30m
30m
Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.

5.0
(1)
17
riders
29.4km
02:01
150m
150m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.

5.0
(2)
11
riders
7.50km
00:36
30m
30m
Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.

7
riders
14.6km
01:18
200m
200m
Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.
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4.5
(4)
37
riders
37.5km
02:09
120m
120m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
7
riders
43.6km
02:43
400m
400m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

3.0
(2)
12
riders
11.8km
00:46
130m
130m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
8
riders
50.2km
03:04
420m
420m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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5.0
(1)
32
runners
7.38km
00:46
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
25
runners
7.73km
00:48
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
8
runners
5.49km
00:34
20m
20m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.0
(1)
5
runners
14.7km
01:34
160m
160m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Head Of The Harbor offers opportunities for hiking, road cycling, mountain biking, and jogging. The region features 8 routes across these sports. Over 1,000 visitors have rated routes in the area, with an average of 4.67 out of 5 stars.
Popular hiking options include the 2.9-mile (4.7 km) loop trail at Avalon Nature Preserve, offering diverse ecosystems and coastal views. Caleb Smith State Park Preserve also features a 3.0-mile (4.8 km) loop through woods. The Stony Brook Harbor Walk provides a 1-mile (1.6 km) stroll with historical information.
The Avalon Nature Preserve offers an easy 2.9-mile (4.7 km) loop trail suitable for beginners. The Stony Brook Harbor Walk is another accessible option, providing a 1-mile (1.6 km) stroll. For more options, consult the Easy hikes around Head Of The Harbor guide.
The winding country roads of Head Of The Harbor are suitable for road cycling. Longer regional routes include the 48.8-mile (78.5 km) Mount Sinai Harbor Loop and the 30.4-mile (49 km) Cordwood Park – Old Field Point Light loop. The Setauket-Port Jefferson Station Greenway Trail, a 3-mile (4.8 km) paved path, is also available.
While specific mountain biking trails within Head Of The Harbor are not prominently highlighted, nearby Hempstead Harbor Woods on Long Island offers a dedicated trail system. This system features various loops with differing difficulty levels for mountain biking enthusiasts. Consult the MTB Trails around Head Of The Harbor guide for more information.
The scenic winding country roads of Head Of The Harbor, along with paths like the Avalon Nature Preserve loop and the Setauket-Port Jefferson Station Greenway Trail, provide opportunities for jogging. Several running loops are also accessible from neighboring Saint James and Stony Brook. The Running Trails around Head Of The Harbor guide offers further details.
Stony Brook Harbor is a central natural feature, with efforts to preserve its 19th-century appearance. Locations like the Avalon Nature Preserve showcase diverse ecosystems, including woodlands, wetlands, and meadows. The village is known for its picturesque scenery, which includes undulating terrain and a blend of residential and agricultural lands.
Rules regarding dogs vary by specific preserve or park. Visitors should check the regulations for individual locations such as Avalon Nature Preserve or Caleb Smith State Park Preserve before bringing pets. Leash requirements are common in most natural areas.
Komoot offers several guides for the region, including Hiking around Head Of The Harbor, Easy hikes around Head Of The Harbor, and Road Cycling Routes around Head Of The Harbor. Guides for mountain biking, jogging, and general cycling are also available.
The official website for the Village of Head Of The Harbor is headoftheharborny.gov. The main phone number for the Village Hall is +1-631-584-5550.
The Avalon Nature Preserve offers an easy loop trail suitable for families. The Stony Brook Harbor Walk is another accessible option, providing a gentle stroll with historical and natural points of interest.
Routes in Head Of The Harbor have an average rating of 4.67 out of 5 stars on komoot. This rating is based on experiences shared by more than 1,000 visitors who have explored the region's 8 routes.

