Southold, a region on the North Fork of Long Island, New York, provides diverse landscapes for outdoor activities. Its geography, characterized by coastal areas along the Long Island Sound and Peconic Bay, combined with a relatively flat topography, makes it suitable for several sports like hiking, road cycling, jogging, and touring cycling. The area features woodlands, meadows, and significant natural preserves, offering varied terrain for exploration.
Outdoor enthusiasts exploring Southold can find more than 20…
38
Routes
4.5
(11)
Average rating
436
People visited

19
hikers
8.91km
02:18
50m
50m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

10
hikers
2.81km
00:44
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

1.43km
00:22
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

968m
00:15
0m
0m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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5
runners
13.1km
01:36
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

13
runners
9.96km
01:02
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

13
runners
12.5km
01:19
90m
90m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

9
runners
5.73km
00:36
20m
20m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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4.8
(4)
82
riders
47.5km
02:17
360m
360m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

5.0
(1)
43
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

15
riders
164km
06:27
660m
660m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

9
riders
50.4km
02:03
150m
150m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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5.0
(1)
39
riders
55.4km
03:26
330m
330m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.0
(1)
21
riders
47.9km
02:43
120m
120m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

10
riders
17.3km
01:00
50m
50m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

4
riders
19.4km
01:08
60m
60m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Southold offers a variety of outdoor activities, including hiking, road cycling, jogging, and touring cycling. The region features diverse landscapes such as woodlands, meadows, and coastal areas along the Long Island Sound and Peconic Bay. There are 22 routes available, with an average rating of 4.6 stars from more than 900 visitors.
The Arshamomaque Pond Preserve is a notable hiking destination in Southold, offering woodlands, meadows, and wetlands. Other trails include the Mattituck-Cutchogue Loop, Southold Bayview Loop, Southold Soundview Loop, and Orient Loop. For more options, consult the Hiking around Southold guide.
Southold's relatively flat topography makes many trails accessible for various fitness levels. The Arshamomaque Pond Preserve offers paths through woodlands and meadows suitable for easier walks. For specific easy options, refer to the Easy hikes around Southold guide.
Southold provides scenic routes for both road and touring cycling, often with coastal views. A popular touring route is the Hashamomuck Beach – Orient Beach State Park loop, which is approximately 30 miles (48 km) long. Wine country bike tours are also available, allowing cyclists to explore local vineyards. More routes can be found in the Cycling around Southold guide.
Yes, Southold offers tranquil roads and scenic routes for road cycling, often featuring views of the Long Island Sound and Peconic Bay. The region's flat terrain is well-suited for this activity. Explore options through the Road Cycling Routes around Southold guide.
Joggers can utilize many of the same trails as hikers and cyclists in Southold. Scenic routes are available within areas like the Arshamomaque Pond Preserve. The Running Trails around Southold guide provides specific options for joggers.
Southold is characterized by its natural endowments, including the Peconic Bays and Long Island Sound, which are federally designated National Estuaries. The Arshamomaque Pond Preserve features diverse ecosystems, and the region also includes numerous beaches and picturesque vineyards.
The Arshamomaque Pond Preserve is recognized for its rich wildlife, including osprey, white-tail deer, and diamondback terrapins. The preserve's diverse habitats, such as tidal wetlands and vernal ponds, support a variety of species. Osprey are typically visible from mid-March to October.
Komoot offers several guides for Southold, including Hiking around Southold, Easy hikes around Southold, Road Cycling Routes around Southold, Running Trails around Southold, and Cycling around Southold.
Southold is a popular destination on komoot, with more than 900 visitors having explored its routes. The 22 available routes across various sports have received an average rating of 4.6 out of 5 stars from 34 ratings.
The official website for the Town of Southold, NY, is southoldtownny.gov. This resource provides information on local government services and community details.
The main phone number for Southold Town Hall is 631-765-1800. For inquiries regarding permits or beach access, the Southold Recreation Department can be reached at 631-765-5182.

