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Running trails & routes
United States
Maine
Cumberland County

Hinckley Park via Winnick Woods loop

Moderate

2.9

(2)

91

runners

Hinckley Park via Winnick Woods loop

00:40

6.26km

40m

Running

Jog this 3.9-mile (6.3 km) moderate loop through the varied terrains of Hinckley Park and Winnick Woods, gaining 125 feet (38 metres).

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

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1

3.95 km

Hinckley Park

Highlight • Parking

With 40 acres, two scenic ponds and stunning fall foliage, Hinckley Park is a charming corner just outside of South Portland.

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B

6.26 km

End point

Parking

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Way Types & Surfaces

Way Types

2.59 km

1.62 km

1.22 km

828 m

Surfaces

2.44 km

2.35 km

1.21 km

240 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

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Today

Sunday 5 July

27°C

16°C

0 %

Additional weather tips

Max wind speed: 21.0 km/h

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Frequently Asked Questions

Is the 'Hinckley Park via Winnick Woods loop' a single, continuous trail?

No, the 'Hinckley Park via Winnick Woods loop' is not a formally recognized single trail. Hinckley Park is located in South Portland, and Winnick Woods is in Cape Elizabeth, Maine. They are distinct trail systems, each offering its own network of trails for jogging and other activities. This Komoot route connects sections of both parks to create a longer experience.

Where can I park to access Hinckley Park?

You can find parking at Hinckley Park itself. The Highland Avenue parking area is a common starting point, especially if you plan to explore the trails that gain elevation towards Stillman Street.

Are dogs allowed on the trails in Hinckley Park and Winnick Woods?

Yes, both Hinckley Park and Winnick Woods are popular destinations for dog walkers. However, please ensure you observe local leash laws and clean up after your pet to maintain a pleasant experience for all users.

What is the best time of year to jog in Hinckley Park and Winnick Woods?

Both parks offer enjoyable jogging experiences year-round. Spring and fall provide beautiful foliage, but some areas can become quite muddy, so appropriate waterproof footwear is recommended. Summer is pleasant, especially in the wooded sections, and winter jogging is possible with proper gear, though trail conditions may vary.

Do I need a permit or pay an entrance fee for Hinckley Park or Winnick Woods?

No, there are no permits or entrance fees required to access the trails in either Hinckley Park or Winnick Woods. Both parks are open to the public for recreational use.

What is the terrain like for jogging in these parks?

The terrain in both parks is varied, offering an easy to moderate difficulty level. Hinckley Park features woodland stretches, shoreline paths around two ponds, and open pastures, with surfaces including dirt, rock, grass, and gravel. Some sections have uneven, climbing paths and stairs. Winnick Woods offers woodlands, wetlands, a pond, and a meadow, with dirt paths and numerous boardwalks over wet areas. While some sections are flat, grades can be steep in places, and paths go up and down small hills.

What kind of scenery can I expect while jogging in these parks?

In Hinckley Park, you'll enjoy diverse scenery including two scenic ponds fed by Kimball Brook, mini-falls, wooded areas, and open fields. Winnick Woods offers serene woods, wetlands, and an open meadow, with many bridges and boardwalks traversing these natural features. Both parks are home to abundant wildlife, making for a rich natural ambiance.

Are there any specific features or viewpoints to look out for?

In Hinckley Park, look for picturesque overlooks of the ponds and brooks from various bridges and benches, as well as mini-falls at the outlet of each pond. Winnick Woods is known for its extensive network of boardwalks and bridges that wind through scenic wetlands and dense forests.

Are these trails suitable for beginners or families with children?

Yes, both Hinckley Park and Winnick Woods offer sections suitable for beginners and families. While some areas have moderate climbs or uneven terrain, both parks have multiple loop options of varying lengths and difficulties. Winnick Woods, for example, has machine-built trails like the Winnick Wander that are beginner-friendly with consistent grades.

What should I wear or bring for jogging on this route?

Given the varied terrain and potential for muddy sections, especially in spring and fall, we recommend wearing appropriate trail running shoes with good grip. Layers are advisable, as conditions can change. Bring water, especially on warmer days, and consider insect repellent during warmer months. If jogging in winter, dress warmly and be prepared for potentially icy or snowy conditions.

Does this route intersect with other well-known paths?

Yes, the route also passes through sections of the Ocean St Bike Route and the Highland Avenue Bike Route, offering connections to other local pathways.

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