4.5
(3)
157
runners
35
runs
Jogging around Southold offers diverse natural landscapes, including extensive trail networks, parks, and preserves. The region features woodlands, wetlands, dunes, and beach habitats, providing varied terrain for runners. Many routes offer scenic water views of the Long Island Sound and various bays. Southold's commitment to maintaining these natural areas ensures a rewarding experience for outdoor exercise.
Last updated: June 29, 2026
5
runners
13.1km
01:36
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
14
runners
9.96km
01:02
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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13
runners
12.5km
01:19
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
11
runners
5.73km
00:36
20m
20m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
10
runners
5.21km
00:32
10m
10m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Southold
Nicoll's Creen is a marshy bay, part of Mashomack Preserve. This area is great for birdwatching and a scenic spot for a break.
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Nestled on Shelter Island, Mashomack Preserve is a 2,039-acre natural wonderland. It features diverse ecosystems from woodlands to tidal creeks, offering picturesque trails for hikers. Rich in biodiversity, it's a haven for birdwatchers and nature enthusiasts, showcasing the beauty of Long Island's wildlife.
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Southold offers a good selection of running routes, with over 25 options available. These routes cater to various preferences, ranging from easy jogs to more challenging runs through diverse landscapes.
You'll find a wide variety of terrain for running in Southold. The region features extensive trail networks through woodlands, wetlands, and even beach habitats. Many routes offer scenic water views of the Long Island Sound and various bays, providing a mix of natural surfaces and coastal paths.
Yes, many of Southold's running routes are designed as loops, offering a convenient way to explore the area. For example, the Joan C. Coles, Red, Yellow, Blue and Green Trail loop is a popular 8.1-mile option traversing diverse ecosystems. Another great choice is the Running loop from Village of Greenport, which offers coastal views and village surroundings.
Many of Southold's preserves and parks are dog-friendly, though it's always best to check specific park regulations. Generally, dogs are welcome on trails if kept on a leash. Places like Inlet Pond County Park and Goldsmith Inlet Park are popular choices for runners with canine companions, offering scenic trails through natural settings.
Absolutely. Southold has several preserves and parks with shorter, less strenuous trails perfect for family jogs. Downs Farm Preserve in Cutchogue, for instance, offers a mile of passive recreation trails that are easy to navigate. Mill Road Preserve also features a 1.2-mile trail through varied landscapes, suitable for families.
Southold's running routes often pass through beautiful natural areas and offer stunning views. You can enjoy water views of the Long Island Sound at places like Inlet Pond County Park or Goldsmith Inlet Park. The Mashomack Preserve, though on Shelter Island, is a significant natural wonderland with diverse ecosystems. You might also encounter historical sites like Fort Corchaug at Downs Farm Preserve.
Yes, Southold is home to several preserves with extensive trail networks ideal for longer runs. The Mashomack Preserve (accessible from Southold) offers an 8.2-mile loop with varied scenery. Laurel Lake Preserve also boasts a 2.1-mile nature trail that traverses woodlands, grasslands, and offers views of Laurel Lake, perfect for a longer, immersive run.
Most major preserves and parks in Southold, such as Inlet Pond County Park, Goldsmith Inlet Park, and Downs Farm Preserve, provide dedicated parking areas for visitors. For specific details on parking facilities, you can often find information on the individual park or preserve websites, or check the Southold Town Parks & Beaches page for general guidance: Southold Town Parks & Beaches.
While many of Southold's preserves and parks are best accessed by car, some areas, particularly those closer to villages like Greenport, might be reachable via local public transport options or within walking distance from bus stops. For routes like the Running loop from Village of Greenport, public transport might be a viable option to get to the starting point. It's advisable to check local bus schedules for specific routes.
The running routes in Southold are highly regarded by the komoot community, with an impressive average score of 5.0 stars from reviews. Over 110 runners have explored these trails, often praising the diverse ecosystems, scenic water views, and the well-maintained nature of the paths that make for a rewarding outdoor experience.
Generally, most public trails and preserves in Southold are open to the public from dawn to dusk without requiring specific permits for jogging. However, it's always a good idea to check the official Southold Town website for any updates or specific regulations regarding certain preserves or activities. You can find more information on trails and stewardship here: Southold Town Trails and Stewardship.
Southold offers great jogging opportunities year-round. Spring and fall provide pleasant temperatures and beautiful scenery with changing foliage or blooming wildflowers. Summer is also popular, especially for coastal runs, though it can be warmer. Even in winter, many trails remain accessible, offering a peaceful experience amidst the natural beauty.


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